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Quality Control of [ 24242-20-4 ] Purity: 98% SDS Specification

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Product Details of [ 24242-20-4 ]

CAS No. :	24242-20-4
Formula :	C₆H₆N₂O₂
M.W :	138.12
SMILES Code :	NC1=CN=C(C=C1)C(=O)O
MDL No. :	MFCD02684600
InChI Key :	WDJARUKOMOGTHA-UHFFFAOYSA-N
Pubchem ID :	4179726

Safety of [ 24242-20-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 24242-20-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	35.6
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	76.21 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.32
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.37
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.72
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.19

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.09
Solubility	11.1 mg/ml ; 0.0807 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.18
Solubility	9.07 mg/ml ; 0.0657 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.01
Solubility	13.5 mg/ml ; 0.0977 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.12 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.42

Application In Synthesis of [ 24242-20-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 24242-20-4 ]
Downstream synthetic route of [ 24242-20-4 ]

[ 24242-20-4 ] Synthesis Path-Upstream 1~2

1
[ 24242-20-4 ]
[ 32046-43-8 ]

References: [1] Pharmazie, 1983, vol. 38, # 9, p. 591 - 596.
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 10, p. 933 - 945.

2
[ 24242-20-4 ]
[ 323578-38-7 ]

References: [1] Patent: WO2011/59839, 2011, A1, .
[2] Patent: US2015/158864, 2015, A1, .
[3] Patent: EP2768509, 2017, B1, .
[4] Patent: WO2013/59587, 2013, A1, .

[ 24242-20-4 ] Synthesis Path-Downstream 1~33

1
[ 110-86-1 ]
[ 24242-20-4 ]
[ 108-24-7 ]
[ 86873-62-3 ]

References: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1951,vol. 288,p. 237,241.

2
[ 24242-20-4 ]
[ 14527-26-5 ]
5-guanidinopicolinic acid sulfate [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 260 - 268.

3
[ 24242-20-4 ]
[ 108-24-7 ]
[ 86873-62-3 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

4
[ 24242-20-4 ]
[ 103-72-0 ]
5-(N'-phenylthioureido)picolinic acid [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 260 - 268.

5
[ 24242-20-4 ]
[ 123-62-6 ]
[ 75903-35-4 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

6
[ 24242-20-4 ]
[ 556-61-6 ]
5-(N'-methylthioureido)picolinic acid [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 260 - 268.

7
[ 24242-20-4 ]
[ 592-82-5 ]
5-(N'-butylthioureido)picolinic acid [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 260 - 268.

8
[ 24242-20-4 ]
[ 30766-11-1 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

9
[ 24242-20-4 ]
[ 32046-43-8 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.
[2]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 933 - 945.

10
[ 24242-20-4 ]
[ 100-36-7 ]
[ 957344-88-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20℃; for 48h;	The 5-aimno-pypidme-2-carboxylic acid is coupled to N,N-diethyl-ethane-l,2-diamine(0 47mL, 3 32mmol), m the presence of O-(7-azabenzotriazol-l-yl)-lambdar,lambdar,iV',lambdar -tetramethyluronium hexafluorophosphate (1 26g, 3 33mmol), and DIPEA (0 59mL, 3 33mmol) m THF (10 mL) The mixture is stirred at room temperature for 48 hours The solvent is removed in vacuo and the residue partitioned between water-EtOAc The organic layer is dpied over MgSpsi4, filtered and concentrated to give a residue purified by silica gel column chromatography 5-Ammo-pypidme-2-carboxylic acid (2- diethylammo-ethyl)-amide is isolated (394mg, 100percent) elutmg with 96 4 DCM NH3 (7M in MeOH)

References: [1]Patent: WO2007/131991,2007,A1 .Location in patent: Page/Page column 57.

11
[ 24242-20-4 ]
N-<2-(t-butylcarbamoyl)-ethyl>-5-iodopyridine-2-carboxamide [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 933 - 945.

12
[ 4487-59-6 ]
[ 24242-20-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1995,vol. 36,p. 933 - 945.
[2]Pharmazie,1983,vol. 38,p. 591 - 596.
[3]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1951,vol. 288,p. 237,241.

13
[ 24242-20-4 ]
[ 29082-92-6 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

14
[ 24242-20-4 ]
[ 66933-04-8 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

15
[ 4214-76-0 ]
[ 24242-20-4 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1951,vol. 288,p. 237,241.

16
[ 100367-55-3 ]
[ 24242-20-4 ]

References: [1]Pharmazie,1983,vol. 38,p. 591 - 596.

17
[ 59290-34-5 ]
[ 24242-20-4 ]

References: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1951,vol. 288,p. 237,241.

18
methanol-3 N sodium hydroxide-35% aqueous hydrogen peroxide [ No CAS ]
[ 55338-73-3 ]
[ 24242-20-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	In water;	(a) 3-Amino-6-pyridinecarboxyamide 3-Amino-6-pyridinecarbonitrile (0.45 g) was mixed with 5 ml of methanol-3 N sodium hydroxide-35percent aqueous hydrogen peroxide (2:3:1 (v/v)). After stirring at room temperature for 30 minutes, 5 ml of water was added to precipitate a solid. The precipitated solid was collected by filtration, and washed with water and acetone, followed by drying. Thus, 0.29 g of a white powder was obtained (yield: 56percent).

References: [1]Patent: US5262415,1993,A .

19
[ 67-56-1 ]
[ 24242-20-4 ]
[ 67515-76-8 ]

Yield	Reaction Conditions	Operation in experiment
78%		Thionyl chloride (12.9 g, 109 mmol) was added to methanol (60 mL) at 0 C. The reaction mixture was stirred at 0 C for 1 h before 5-aminopicolinic acid (3.0 g, 21 .7 mmol) was added. The reaction solution was refluxed for 4 h. The reaction solution was cooled to room temperature and concentrated. The crude residue was dissolved in water (100 mL) and treated with saturated aqueous of sodium bicarbonate (30 mL). The aqueous layer was extracted with ethyl acetate (1 00 mL c 3). The combined organic layers were washed with brine (1 00 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give methyl 5-aminopicolinate (2.6 g, 1 7.1 mmol, 78%) as a yellow oil. LCMS (ESI) m/z: 153.0 [M+H]+. Used in the next step directly without additional purification.
73%	With thionyl chloride; at 0℃; for 96h;Reflux;	Step 1. Methyl 5-aminopicolinate. To a stirred solution of 5-aminopicolinic acid (170 g, 1.23 mol) in MeOH (1700 ml) was added SOCl2 (178.6 ml, 2.47 mol) at 0 C. The reaction mixture was then refluxed for 72 h. The mixture was then cooled to 0 C. and additional SOCl2 was added (40 ml, 0.55 mol). The mixture was then refluxed for 24 h. The excess SOCl2 was removed under reduced pressure and the crude material was neutralized with aq. NaHCO3. The mixture was filtered and the filter cake dried at 40-50 C. overnight. The solid was collected to give methyl 5-aminopicolinate (350 g). The filtrate was further extracted with DCM (3×2 L). The organic extract was washed with brine, dried (Na2SO4) and concentrated to dryness to afford crude compound (200 g). All of solids were collected to give methyl 5-aminopicolinate (550 g from 680 g of compound 1, 73%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.12 (d, J=2.5 Hz, 1H), 7.93 (d, J=8.5 Hz, 1H), 6.97 (dd, J=2.8, 8.5 Hz, 1H), 4.24 (br s, 2H), 3.93 (s, 3H).
63%	With thionyl chloride; at 80℃; for 12h;Inert atmosphere;	General procedure: A mixture of 4-aminobenzoic acid (32-34, 5.0 mmol), thionyl chloride(1.487 g, 5.0 mmol), and MeOH (20.0 mL) was flushed with argon, and stirred at80C for 12 hours. Remove reaction solvent by rota vapor. The reaction mixture wasneutralized with NaHCO3(sat) (20.0 mL) and extracted with ethyl acetate (100 mL ×3). The combined organic extracts were washed with brine, dried by Na2SO4, filtered,and evaporated, to get cmopound 35-37 (63-89%) as a white solid.

39%	With thionyl chloride; In methanol; at 0℃; for 24h;Reflux;	103451 5-Aminopyridine-2-carboxylic acid (2.00 g, 14.5 mmol) was dissolved in anhydrous methanol (20 mL) and cooled to 0 C. Thionyl chloride (3.15 mL, 43,4 mmol) was added drop-wise over 5 minutes and the mixture allowed to warm to room temperature then heated to reflux for 24 hours. The reaction mixture was concentrated, partitioned between ethyl acetate (30 mL) and saturated aqueous sodium bicarbonate solution (30 mL). The mixture was sonicated, the layers separated and the aqueous layer extracted with ethyl acetate (2 x 15 mL), The combined organic extracts were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound 850 mg (39% yield) as an off- white powder. oH NMR (500 MHz, DMSO) 7.97 (d, J = 2.7 Hz, 1H), 7.74 (d, J = 8.6 Hz, 1H), 6.91 (dd, J = 8.6, 2.7 Hz, 1H), 6.18 (s, 2H), 3.76 (s, 3H).
	With acetyl chloride;	Synthesis 255-(3,5-Dichloro-4-ethoxybenzamido)picolinic acid (AAA-026)5-(3,5-Dichloro-4-ethoxybenzamido)picolinic acid (AAA-026) (20 mg, quant, for final step) was prepared in essentially the same manner as in Steps (Hi) and (iv) for AAA-001 , except that 3,5-dichloro-4-ethoxybenzoic acid and methyl 5-aminopicolinate (prepared by treating <strong>[24242-20-4]5-aminopyridine-2-carboxylic acid</strong> with acetyl chloride and methanol) were used instead of 3,5-dichloro~4-(cyclopentyloxy)benzoic acid and methyl 4-aminobenzoate respectively in step (Hi): m/z 355 (M+H)+ (ES+). 1H NMR 400 MHz, DMSO-de) delta: 10.9 (1 H, s), 9.0 (1 H, d), 8.4 (1 H, dd), 8.2 (2H, s), 8.1 (1 H, d), 4.1 (2H, q), 1.4 (3H, t). (The final compound was isolated as a hydrochloride salt.
		5-Amino-2- nicotinic acid (6.38 g) was dissolved in methyl alcohol (50 mL) and then cooled to 0 0C in an ice- water bath. Thionyl chloride (8.3 mL) was then added to the solution. The reaction mixture was refluxed for 3O h. After evaporating the methanol, the residue was neutralized with a saturated solution of sodium bicarbonate and was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and filtered. The filtrate was concentrated to give 2.31 g of the final ester (Rf: 0.473 min, Condition B, M+H+: 153).

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 413 - 417.
[2]Patent: WO2019/183587,2019,A1 .Location in patent: Page/Page column 229.
[3]Patent: US2015/158864,2015,A1 .Location in patent: Paragraph 0292.
[4]European Journal of Medicinal Chemistry,2017,vol. 140,p. 42 - 51.
[5]Journal of Medicinal Chemistry,2011,vol. 54,p. 7232 - 7246.
[6]Patent: WO2016/33445,2016,A1 .Location in patent: Paragraph 0345.
[7]Patent: WO2011/27106,2011,A1 .Location in patent: Page/Page column 92-93.
[8]Patent: WO2006/112828,2006,A1 .Location in patent: Page/Page column 81.

20
[ 55338-73-3 ]
[ 24242-20-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid; at 90 - 100℃; for 4h;	Intermediate 76. 5-aminopyridine-2-carboxylic acid A solution of 5-amino-2-cyanopyridine (10. Og, 83.9mmol) in sulfuric acid (50ml_) was placed in a high pressure vessel and heated to 90 °C for 2h. Then, water was added to the mixture (100ml_) and the reaction was heated to 100 °C for 2 additional hours. The obtained orange solution was poured over a mixture of ice and water and stirring was maintained for 15 min (a pale beige solid precipitated from the solution) and the solid obtained was filtered, washed with cold water and dried under vacuum overnight to afford the title compound (1 1 .7g, 100percent) LRMS (m/z): 139 (M+1 )+
64.68%	With sulfuric acid; water; at 100℃; for 2h;	Synthesis of compound 206.2. The solution of 206.1 (4.0g, 33.61mmol, l .Oeq) in concentrated H2S04 (20ml) was heated at 100 °C for 2h. Further water (20 ml) was added to the reaction mixture and it was heated at 100 °C for 2 h. After completion of reaction, reaction mixture was poured in ice cold water and product was filtered to get pure 206.2 (3.0g, 64.68percent). MS (ES): m/z 138.13 [M+H]+.
	With sodium hydroxide; water; In ethanol; at 120℃;	Step 1 5-Amiotano-pyriotadiotane-2-carboxyliotac acid (2-diotaethylamiotano-ethyl)-amiotade o fI H[00274] 5-Aminopyridme-2-carbomtpile (0 2g, mmol) is stirred m a mixture of EtOH (ImL) and48percent aq NaOH (ImL) at 12O0C overnight The solvent is removed in vacuo and the water residue is <n="59"/>washed with EtOAc The water layer is acidified to pH 5 and concentrated to afford the crude 5-ammo- pypidme-2-carboxylic acid (0 23 g, 0 168mmol)

The 5-amino-2-cyanopyridine (4.0 g) was added to sulfuric acid (20 mL) slowly with stirring. The reaction mixture was stirred at 90 0C for 2 h in a sealed tube. The reaction mixture was diluted with water (40 mL) and heating was continued at 100 0C for 2 h. The reaction mixture was cooled to room temperature and was poured into ice. The solid thus separated was filtered, washed with cold water and was dried under vacuum to yield 6.4 g of the desired product (Rf: 0.173 min, Condition B, M+H+: 139).

References: [1]Patent: WO2016/46390,2016,A1 .Location in patent: Page/Page column 68.
[2]Dyes and Pigments,2011,vol. 88,p. 366 - 371.
[3]Patent: WO2015/131080,2015,A1 .Location in patent: Paragraph 001078; 001079.
[4]Patent: WO2007/131991,2007,A1 .Location in patent: Page/Page column 56-57.
[5]Patent: WO2006/112828,2006,A1 .Location in patent: Page/Page column 81.

21
[ 24242-20-4 ]
[ 929301-65-5 ]
6-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)pyridin-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%		Example 55 6-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undec-3-yl} carbonyl)pyridin-3-amine trifluoroacetateA mixture of Intermediate A (77 mg, 0.20 mmol), l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (42 mg, 0.22 mmol), 5-aminopicolinic acid (30 mg, 0.22 mmol), triethylamine (140 mul, 1.0 mmol) and acetonitrile (1 ml) was stirred at room temperature overnight and acidified with acetic acid. The crude product was purified by preparative HPLC (RP- 18, gradient acetonitrile/water/TFA from 10/90/0.1 to 95/5/0.1) to give the product as a white solid (9 mg, 11percent).1H NMR (399.99 MHz, CD3OD) delta 7.96 (d, IH), 7.44 (d, IH), 7.29 (d, IH), 7.22-7.17 (m, 2H), 6.93 (t, IH), 4.28 (s, 2H), 3.75-3.52 (m, 2H), 3.44-3.35 (m, 3H), 3.25-3.13 (m, 2H), 3.11 (m, 3H), 2.04 (d, 2H), 1.78-1.58 (m, 6H), 1.54 (s, 6H)APCI-MS m/z: 435.6 [MH+]HPLC (Method A) Retention time: 5.34 minHPLC (Method B) Retention time: 7.75 min

References: [1]Patent: WO2007/30061,2007,A1 .Location in patent: Page/Page column 130.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 7706 - 7723.

22
[ 24242-20-4 ]
[ 119830-47-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Step 2 A stirred suspension of <strong>[24242-20-4]3-amino-pyridine-6-carboxylic acid</strong> (25 g) in ethanol (300 mL) at 0° C. was saturated with gaseous hydrogen chloride. The mixture was allowed to warm to 23° C. and heated to reflux for 2 hours. A clear solution was obtained. After cooling to 23° C., the mixture was concentrated in vacuo, neutralized with aqueous NaHCO3 and extracted with ethyl acetate. The organic phase was washed with water, dried over MgSO4, and concentrated in vacuo to give ethyl 3-amino-pyridine-6-carboxylate as a pale yellow solid.

References: [1]Patent: US6689754,2004,B1 .

23
[ 24242-20-4 ]
[ 1036488-09-1 ]
[ 1036488-27-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; N,N-dimethyl acetamide; at 70℃; for 48h;	Example 19 Methyl 5 - \\4-(( 1 R,2S)-2-isopropylcarbamoyl-cy clopentylamino)-5 -trifluoromethyl- pyrimidin-2-ylaminol -pyridine-2-carboxylate-( 1 -methyl-piperidin-4-yl)-amide 300 mg (0.86 mmol, 1 eq) A-2a are dissolved in 1 mL DMA, 154 mg (1.11 mmol, 1.3 eq) <strong>[24242-20-4]5-aminopyridine-2-carboxylic acid</strong> are added and the reaction mixture is then combined with 492 muL (1.97 mmol, 2.3 eq, 4 M in dioxane) hydrochloric acid. The reaction mixture is stirred for 48 h at 700C, combined directly with RP gel, the volatile constituents are eliminated in vacuo and the product is purified by column chromatography (water/MeCN 78/22 (+ in each case 0.2percent HCOOH) to 60/40 in 15 min). Corresponding product fractions are combined and freed from the solvent by freeze-drying. 11 mg of 5-[4-((lR,2S)-2- isopropylcarbamoyl-cyclopentylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-pyridine- 2-carboxylic acid are obtained. MS-ESI+: 453 (M+H)+

References: [1]Patent: WO2008/77885,2008,A2 .Location in patent: Page/Page column 37.

24
[ 24242-20-4 ]
[ 67515-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	With diazomethyl-trimethyl-silane; In methanol; diethyl ether; benzene; at 0 - 20℃; for 6h;	5-Amino-pyridine-2-carboxylic acid 1 (5.4 mmol) is dissolved in benzene : MeOH = 3 :1 (40 niL) and cooled in an ice-bath to 00C. To the solution is slowly added 2M TMSCH2N2 in Et2O solution (6.5 mmol). After the addition is complete, the reaction mixture is warmed to rt and stirred for 6 h. After removing the solvent in vacuum, methyl 5-aminopicolinate 2 is obtained and used in the next step without further purification. MS (m/z) (M+l)+: 153.1.

References: [1]Patent: WO2009/26204,2009,A1 .Location in patent: Page/Page column 43.

25
[ 24242-20-4 ]
[ 64-17-5 ]
[ 119830-47-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With thionyl chloride; at 0℃;Inert atmosphere; Reflux;	To a solution of 5-aminopicolinic acid (13.5 g, 97.7 mmol) in anhydrous ethanol (200 mL) was added SOCl2 (60.0 mL, 504 mmol) dropwise at 0 C. under N2 atmosphere. The resulting mixture was heated at reflux and stirred overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in a saturated aqueous NaHCO3 solution so that that pH of the solution was approximately pH 9-10. The reaction mixture was extracted with EtOAc (8×250 mL). The combined organic phases were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound as a brown solid (14.3 g, 88%) 1H NMR (CDCl3) delta 8.14 (d, 1H), 7.94 (d, 1H), 6.97 (dd, 1H), 4.41 (q, 2H), 4.16 (br s, 2H), 1.39 (t, 3H)
83%	With thionyl chloride; at 10 - 110℃;	Thionyl chloride (5.2 ml, 71.3 mmol) was added dropwise to <strong>[24242-20-4]5-amino-pyridine-2-carboxylic acid</strong>(4.0 g, 29.0 mmol) in EtOH (30 ml) whilst maintaining the temperature of the mixture below 100C. During the addition the mixture became very thick and more EtOH (20 ml) was added. The mixture was then stirred and heated at 95C overnight. Next day the temperature was increased to 1 100C and the mixture was heated at this temperature overnight. On cooling to rt the mixture was <n="74"/>concentrated to give a solid. Saturated aqueous sodium hydrogen carbonate solution was added followed by saturated aqueous sodium carbonate solution. Ethyl acetate and water were then added. The organic phase was washed with brine, dried and concentrated to give an off white solid (4.0 g, 83 %). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.27 (3 H, t, /=7.10 Hz), 4.22 (2 H, q, 7=6.87 Hz), 6.19 (2 H, s), 6.91 (1 H, dd, 7=8.70, 2.75 Hz), 7.74 (1 H, d, J=8.70 Hz), 7.97 (1 H, d, J=2.29 Hz).
79%	With thionyl chloride; at 0℃; for 19h;Reflux;	To a solution of 5-aminopicolinic acid (194 mg, 1.40 mmol) in ethanol (5 mL), was added thionyl chloride (0.20 mL, 2.80 mmol) at 0 C. The mixture was then stirred under reflux for 19 h, after which time it was cooled to room temperature and the reaction mixture concentrated under reduced pressure. Saturated aqueous sodium carbonate solution was added to the resulting solid to adjust the pH to 9, followed by saturated aqueous sodium hydrogen carbonate. Ethyl acetate (10 mL) and water (10 mL) were added and the organic phase was washed with brine (1 0 mL), dried (Na2SO4), filtered and the filtrate concentrated in vacuo. Ethyl 5-aminopicolinate (184 mg, 79%) was obtained as an off-white solid, with no need for further purification; 1H NMR (500 MHz, MeOD) 6 1 .37 (3H, t, J = 7.1 Hz, CH3), 4.35 (2H, q, J = 7.2 Hz), 7.02 (1H, dd, J = 2.7 and 8.6 Hz, Ar), 7.85 (1H, d, J = 8.6 Hz) and 7.98 (1H, d, J= 2.7 Hz). LRMS(ESI÷) mz 167.2 [M + H].

75%		To a solution of 5-aminopicolinic acid (110; 8.4 g, 60.8 mmol) in ethanol (100 rnL) was added SOCl2 (14.5 g, 120 mmol) at 0 0C. The mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust pH = 9. The resulting mixture was filtered and the solids were dried under reduced pressure to afford ethyl 5-aminopicolinate 111 (7.5 g, 75%).
75%	With thionyl chloride; for 12h;Reflux;	To a solution of 5-aminopyridiencarboxylic acid (16; 8.4 g, 60.8 mmol) inethanol ( 100 mL) was added SOO2 (14.5g, 120 mmol) at 0 C. The mixture was refluxed for 1 2 h. The solvent was removed and saturated Na2C03 solution was added to adjust pH=9 and fi ltrated to give a solid. Dried in vacuo to give ethyl 5-aminopicolinate ( 17; 7.5 g? 75%). M S (ESI) calcd forC8H,oN202 (m/z) 166.18.
75%	With thionyl chloride; at 0℃; for 12h;Reflux;	To a solution of <strong>[24242-20-4]5-aminopyridinecarboxylic acid</strong> (8.4 g, 60.8 mmol) in ethanol (100 mL) was added SOCl2 (14.5 g, 120 mmol) at 0 C. The mixture was refluxed for 12 h. The solvent was removed and saturated Na2CO3 solution was added to adjust pH=9 and filtrated to give a solid. The solid was dried in vacuo to give ethyl 5-aminopicolinate (7.5 g, 75%). MS (ESI) calcd for C8H10N2O2 (m/z): 166.18
75%	With thionyl chloride; at 0℃; for 12h;Reflux;	To a solution of 5-aminopyridiencarboxylic acid (8.4 g, 60.8 mmol) in ethanol (100 mL) was added SOCl2 (14.5 g, 120 mmol) at 0 C. The mixture was refluxed for 12 h. The solvent was removed and saturated Na2CO3 solution was added to adjust pH=9 and filtrated to give a solid. The solid was dried in vacuo to give ethyl 5-aminopicolinate (7.5 g, 75%). MS (ESI) calcd for C8H10N2O2 (m/z): 166.18
72%	With hydrogenchloride; at 65℃; for 96h;	Intermediate 77. ethyl 5-aminopyridine-2-carboxylate 5- aminopyridine-2-carboxylic acid (Intermediate 76, 1 1 , 6g, 84.0mmol) was added to a solution of hydrochloric acid (250ml_ of a 1.25 M solution in ethanol) and the mixture was heated to 65 C for four days. Upon complete cosumption of the starting material, the solvent was evaporated and the residue was suspended in water (300ml_). Solid potassium carbonate was added to the mixture until pH=8 was reached and the aqueous phase was extracted with ethyl acetate (3 x 300ml_). The combined organic extracts were washed with brine (500ml_), dried and concentrated under reduced pressure to afford the title compound (10g, 72%) as an orange solid. LRMS (m/z): 167 (M+1 )+

References: [1]Patent: WO2019/14352,2019,A1 .Location in patent: Paragraph 001807; 001808.
[2]Patent: US2014/315928,2014,A1 .Location in patent: Paragraph 0336; 0337.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 5704 - 5718.
[4]Patent: WO2009/122180,2009,A1 .Location in patent: Page/Page column 72-73.
[5]Patent: WO2016/42341,2016,A1 .Location in patent: Page/Page column 138.
[6]Patent: WO2010/3048,2010,A1 .Location in patent: Page/Page column 114.
[7]Patent: WO2011/59839,2011,A1 .Location in patent: Page/Page column 71.
[8]Patent: WO2013/59587,2013,A1 .Location in patent: Page/Page column 158.
[9]Patent: EP2768509,2017,B1 .Location in patent: Paragraph 0578; 0579.
[10]Patent: WO2016/46390,2016,A1 .Location in patent: Page/Page column 68-69.

26
[ 24242-20-4 ]
[ 1198409-41-4 ]
5-amino-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of delta-amino^-pyridinecarboxylic acid (56mg, 0.40mmol, available from ChemPacific) in DMF (2ml) was added HATU (150mg, 0.40mmol) and DIPEA (0.21 1 ml, <n="119"/>1.21 mmol). The mixture was stirred at room temperature for 20mins then 6-(1 H-indol-4- yl)-1 H-indazol-4-amine (50mg, 0.20mmol) was added and the mixture stirred at room temperature for 18h. The reaction mixture was added to the top of a 2Og aminopropyl cartridge that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 3 h before being eluted with MeOH. The solvent was removed in vacuo to give a crude residue that was dissolved in DMSO/MeOH (1 :1 ) and purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1g aminopropyl column, eluted with DCM/MeOH (1 :1 ) and the solvent removed under a stream of nitrogen to give the title compound (28mg) as a white solid. LCMS (Method B) Rt = 0.90 min, MH+ = 369

References: [1]Patent: WO2009/147190,2009,A1 .Location in patent: Page/Page column 116-117.

27
[ 24242-20-4 ]
[ 765-30-0 ]
[ 1206592-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;	5-Amino-pyridine-2-carboxylic acid (leq.), HATU (1.5 eq.) and Et3N (2eq.) are mixed in DMF at room temperature. Cyclopropylamine (l.leq.) is added to the solution and the reaction mixture is stirred at room temperature for 16hrs. Water is added to the reaction. The organic phases are isolated, dried over MgSO/i, filtered and evaporated under vacuum to afford the expected product. In same cases, purification by flash chromatography is required.

References: [1]Patent: WO2010/10189,2010,A1 .Location in patent: Page/Page column 59.

28
[ 24242-20-4 ]
[ 74-89-5 ]
[ 941284-74-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;	5-Amino-pyridine-2-carboxylic acid (leq.), HATU (1.5 eq.) and Et3N (2eq.) are mixed in DMF at room temperature, methylamine (l.leq.) is added to the solution and the reaction mixture is stirred at room temperature for 16hrs. Water is added to the reaction. The organic phases are isolated, dried over MgS O4, filtered and evaporated under vacuum to afford the expected product. In same cases, purification by flash chromatography is required.

References: [1]Patent: WO2010/10189,2010,A1 .Location in patent: Page/Page column 69.

29
[ 24242-20-4 ]
[ 145255-19-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; triethylamine; at 20℃; for 16h;	This compound was prepared via Method C using <strong>[24242-20-4]5-amino-pyridine-2-carboxylic acid</strong> amide prepared by Method N using ammonia. Method N:[00304] 5-Amino-pyridine-2-carboxylic acid (leq.), EDCI (or HATU) (1.5 eq.), HOBt (1.5eq.)(not used with HATU) and Et3N (2eq.) are mixed in DMF (or THF) at room temperature. An appropriate amine (l .leq.) is added to the solution and the reaction mixture is stirred at room temperature for 16hrs. Water is added to the reaction. The organic phases is isolated, dried over MgSO4, filtered and evaporated under vacuum to afford the expected product. In same cases, purification by flash chromatography is required.
260 mg	With ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 10 - 35℃;	A) 5-aminopyridine-2-carboxamide To a solution of <strong>[24242-20-4]5-aminopyridine-2-carboxylic acid</strong> (2.0 g) in N,N-dimethylformamide (50 mL) were added ammonium chloride (3.9 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.1 mL) and 1-hydroxybenzotriazole (4.4 g), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (260 mg). MS(ESI+): [M+H]+ 138.3.

References: [1]Patent: WO2010/10184,2010,A1 .Location in patent: Page/Page column 61; 79.
[2]Patent: EP2832734,2015,A1 .Location in patent: Paragraph 0783.

30
[ 24242-20-4 ]
C₂₁H₃₂N₂O [ No CAS ]
[ 1179356-36-5 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7706 - 7723.

31
[ 24242-20-4 ]
[ 929518-88-7 ]
6-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)methyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)pyridin-3-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7706 - 7723.

32
[ 24242-20-4 ]
C₂₂H₃₄N₂O₂ [ No CAS ]
[ 1179356-42-3 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7706 - 7723.

33
[ 24242-20-4 ]
C₂₂H₃₄N₂O₂ [ No CAS ]
[ 1179356-44-5 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7706 - 7723.

Historical Records

Technical Information

? Arndt-Eistert Homologation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Passerini Reaction ? Petasis Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

Related Functional Groups of
[ 24242-20-4 ]

Amines

A360903 [67515-76-8]

Methyl 5-aminopicolinate

Similarity: 0.90

A135632 [850689-13-3]

Methyl 4,5-diaminopicolinate

Similarity: 0.82

A173892 [1462-86-8]

3-Aminopicolinic acid

Similarity: 0.80

A101667 [23628-31-1]

6-Aminopicolinic acid

Similarity: 0.78

A104747 [71469-93-7]

Methyl 4-aminopyridine-2-carboxylate

Similarity: 0.78

Carboxylic Acids

A191920 [98-98-6]

2-Pyridinecarboxylic acid

Similarity: 0.87

A137131 [934-60-1]

6-Methyl-2-pyridinecarboxylic acid

Similarity: 0.84

A137453 [30651-24-2]

5-Nitro-2-pyridinecarboxylic acid

Similarity: 0.84

A229562 [4434-13-3]

5-Methylpicolinic acid

Similarity: 0.82

A405225 [177359-60-3]

5-Methylpicolinic acid hydrochloride

Similarity: 0.81

Related Parent Nucleus of
[ 24242-20-4 ]

Pyridines

A360903 [67515-76-8]

Methyl 5-aminopicolinate

Similarity: 0.90

A191920 [98-98-6]

2-Pyridinecarboxylic acid

Similarity: 0.87

A137131 [934-60-1]

6-Methyl-2-pyridinecarboxylic acid

Similarity: 0.84

A137453 [30651-24-2]

5-Nitro-2-pyridinecarboxylic acid

Similarity: 0.84

A229562 [4434-13-3]

5-Methylpicolinic acid

Similarity: 0.82

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CAS No.: 24242-20-4

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Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

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Medicinal Chemistry

Application In Synthesis of [ 24242-20-4 ]

[ 24242-20-4 ] Synthesis Path-Upstream 1~2

[ 24242-20-4 ] Synthesis Path-Downstream 1~33

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 24242-20-4 ]

Amines

Carboxylic Acids

Related Parent Nucleus of
[ 24242-20-4 ]

Pyridines

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CAS No.: 24242-20-4

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Product Details of [ 24242-20-4 ]

Safety of [ 24242-20-4 ]

Computational Chemistry of [ 24242-20-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 24242-20-4 ]

[ 24242-20-4 ] Synthesis Path-Upstream 1~2

[ 24242-20-4 ] Synthesis Path-Downstream 1~33

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Related Functional Groups of [ 24242-20-4 ]

Amines

Carboxylic Acids

Related Parent Nucleus of [ 24242-20-4 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 24242-20-4 ]

Related Parent Nucleus of
[ 24242-20-4 ]