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Quality Control of [ 456-24-6 ] Purity: 97% SDS Specification

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Product Details of [ 456-24-6 ]

CAS No. :	456-24-6
Formula :	C₅H₃FN₂O₂
M.W :	142.09
SMILES Code :	C1=C(C=CC(=N1)F)[N+]([O-])=O
MDL No. :	MFCD03095059
InChI Key :	XOZAJNLUAODXSP-UHFFFAOYSA-N
Pubchem ID :	95264

Safety of [ 456-24-6 ]

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

Computational Chemistry of [ 456-24-6 ] 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	4.0
Num. H-bond donors	0.0
Molar Refractivity	33.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.71 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.99
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	1.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.55
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.	-0.32
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	-0.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.0
Solubility	1.42 mg/ml ; 0.01 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.	-2.27
Solubility	0.767 mg/ml ; 0.00539 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-1.66
Solubility	3.11 mg/ml ; 0.0219 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	Yes
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.	-6.15 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.	0.55

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	3.0 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)	2.05

Application In Synthesis of [ 456-24-6 ]

* 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.

Downstream synthetic route of [ 456-24-6 ]

[ 456-24-6 ] Synthesis Path-Downstream 1~33

1
[ 456-24-6 ]
[ 459-73-4 ]
[ 98997-45-6 ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1020,1024.

2
[ 456-24-6 ]
[ 95-53-4 ]
(5-nitro-[2]pyridyl)-o-tolyl-amine [ No CAS ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1020,1024.

3
[ 456-24-6 ]
[ 5446-92-4 ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1020,1024.

4
[ 4214-76-0 ]
[ 456-24-6 ]
[ 5418-51-9 ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1020,1024.

5
[ 4548-45-2 ]
[ 456-24-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium fluoride; In dimethyl sulfoxide; at 70℃; for 18h;Heating / reflux;	To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70° C. for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30percent ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84percent) of 2-fluoro-5-nitropyridine as an oil, which was used in the following procedure. To 76 g of 2-fluoro-5-nitropyridine in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70percent) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91° C.; mass spectrum (m/e): M+H 112.7.
84%	With potassium fluoride; In dimethyl sulfoxide; at 70℃; for 18h;	To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70C for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30percent ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84percent) of 2-fluoro-5-nitropyridine as an oil, which was used in the following procedure. To 76 g of 2-fluoro-5-nitropyridine in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70percent) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91C; mass spectrum (m/e): M+H 112.7.
	With potassium fluoride; In diethyl ether; water; benzene;	A mixture of 5-nitro-2-chloropyridine (2.0 g, 12.6 mmol) and anhydrous potassium fluoride (2.2 g, 38 mmol) in a combination of sulfalone (6 mL) and benzene (4 mL) was stirred at RT for 20 min. The benzene was then removed by distillation. The resulting mixture was heated at 150° C. for 12 h. The mixture was cooled to RT whereupon water (60 mL) was added. The desired product was separated from the solution via steam distillation. Extraction of the distillate with diethyl ether (2*10 mL) followed by drying (Na2SO4) and concentration gave 5-nitro-2-fluoropyridine as a water white oil (1.3 g, 73percent).

	With potassium fluoride; In diethyl ether; water; benzene;	A mixture of 5-nitro-2-chloropyridine (2.0 g, 12.6 mrnol) and anhydrous potassium fluoride (2.2 g, 38 mmol) in a combination of sulfalone (6 nmL) and benzene (4 mL) was stirred at RT for 20 min. The benzene was then removed by distillation. The resulting mixture was heated at 150° C. for 12 h. The mixture was cooled to RT whereupon water (60 mL) was added. The desired product was separated from the solution via steam distillation. Extraction of the distillate with diethyl ether (2*10 mL) followed by drying (Na2SO4) and concentration gave 5-nitro-2-fluoropyridine as a water white oil (1.3 g, 73percent).
119.4 g (83%)	With cesium fluoride; In 1,2-dimethoxyethane;	Method A Preparation of 2-Fluoro-5-nitropyridine A suspension of 160 g (1.01 mol) of 2-chloro-5-nitropyridine and 379 g of dry cesium fluoride was placed in a dry stainless steel bomb which was then charged with 1 L of anhydrous ethylene glycol dimethyl ether. The bomb was sealed, and the reaction was heated at 130° C. with vigorous stirring for 18 hours. The reactor was cooled, vented, and the contents suspended by vigorous agitation. The solids were collected by filtration, then washed well with dichloromethane. The resulting dark brown filtrate was concentrated at 45° C. to give a thick oily brown residue that was distilled through a 4-inch Vigreux column at 61° C./0.05 mm Hg (literature bp 86-87° C./7 mm Hg; Finger G. C. and Starr L. D., J. Am. Chem. Soc., 81:2674-2675 (1959)) to afford 119.4 g (83percent) of the product as a clear pale yellow oil, >96percent pure by gas chromatography (GC). Nuclear magnetic resonance spectroscopy (1H NMR) in deuterated chloroform (CDCl3): delta9.15 (dd, J=2.7, 0.7 Hz, 1H), 8.63 (td, J=7.7, 2.9 Hz, 1H), and 7.15 (dd, J=9.3, 3.4 Hz, 1H).

References: [1]Chemistry Letters,1993,p. 509 - 512.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1411 - 1416.
[3]Patent: US6355636,2002,B1 .Location in patent: Page column 64.
[4]Patent: EP1171440,2004,B1 .Location in patent: Page 53.
[5]Tetrahedron,1980,vol. 36,p. 1931 - 1936.
[6]Journal of the American Chemical Society,1959,vol. 81,p. 2674.
[7]Tetrahedron Letters,1987,vol. 28,p. 111 - 114.
[8]Heterocycles,1992,vol. 34,p. 1507 - 1510.
[9]Tetrahedron Letters,1987,vol. 28,p. 111 - 114.
[10]Patent: US2002/193597,2002,A1 .
[11]Patent: US2001/49444,2001,A1 .
[12]Patent: US6313292,2001,B1 .
[13]Chemical Communications,2014,vol. 50,p. 9650 - 9652.
[14]Journal of Organic Chemistry,2015,vol. 80,p. 12137 - 12145.

6
[ 372-48-5 ]
[ 456-24-6 ]
C₅H₄FN₂O₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3006 - 3009.

7
[ 456-24-6 ]
[ 1827-27-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 5%-palladium/activated carbon; hydrogen; sodium sulfate; In toluene; for 15h;	0.282 g of 5% Pd / C and lOmmol of anhydrous sodium sulfate were added to a 100 mL round bottom flask containing 50 mmol of <strong>[456-24-6]5-nitro-2-fluoropyridine</strong> in 50 ml of toluene, then hydrogen gas was added and heated and stirred for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, suction filtered, spin-evaporated, recrystallized and dried in vacuo to give 1.6806 g of 5-amino-2-fluoropyridine as a solid product in 75% yield.
70%	With hydrogen;nickel; In ethyl acetate; for 18h;	To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70 C. for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30% ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84%) of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> as an oil, which was used in the following procedure. To 76 g of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70%) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91 C.; mass spectrum (m/e): M+H 112.7.
70%		To 100 g of 2-chloro-5-nitropyridine (Aldrich) in 600 mL of dimethyl sulfoxide under an inert atmosphere was added 100 g of anhydrous KF. The reaction was heated at 70C for 18 hours before cooling and diluting with 500 mL each of brine, ethyl acetate, and hexanes. This mixture was filtered through a pad of celite, the organic phase was separated, and the aqueous phase was extracted three times with equal volumes of ethyl acetate and hexanes. The pooled organic phases were washed with brine, dried with anhydrous sodium sulfate, and stripped of the solvents. This crude product was passed through a plug of silica gel with a gradient of 10-30% ethyl acetate/hexanes and stripped to constant weight on a rotary evaporator to give 76 g (84%) of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> as an oil, which was used in the following procedure. To 76 g of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 500 ml of ethyl acetate under nitrogen was added 100 g of Raney nickel which had been washed three times with ethanol and three times with ethyl acetate. The nitrogen was replaced with hydrogen and the reaction was allowed to proceed for 18 hours at 30 lb/in2. After the hydrogen atmosphere had been replaced by nitrogen, the reaction was filtered through celite and stripped of solvent. The product was purified by passing through a plug of silica gel with chloroform and recrystallized from chloroform to give 42 g (70%) of 6-fluoro-pyridin-3-ylamine in two crops as white platelets: melting point 90-91C; mass spectrum (m/e): M+H 112.7.

	palladium on charcoal; In toluene;	Method A Preparation of 5-Amino-2-fluoropyridine A solution of 5 g (35 mmol) <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> in 100 mL of toluene was hydrogenated over a mixture of 5% palladium on charcoal and anhydrous sodium sulfate until the uptake of hydrogen ceased. The solids were filtered off, the residue was washed with ethyl acetate, and the combined organic solutions were evaporated to give 3.7 (94%) of 5-amino-2-fluoropyridine as a white solid. Recrystallization from dichloromethane-hexanes gave the product mp 89-90 C. (literature mp 87-87.5 C.; Finger G. C., Starr L. D., Roe A., and Link W. J., J. Org. Chem., 27:3965-3968 (1967)). 1H NMR (CDCl3): delta7.62 (t, J=2.3 Hz, 1H), 7.11 (td, J=7.7, 3.0 Hz, 1H), 6.72 (dd, J=8.7, 3.3 Hz, 1H), and 3.74 (br s, 2H).
30.9 g (75%)	palladium-carbon; In ethanol;	12b. 5-Amino-2-fluoropyridine <strong>[456-24-6]<strong>[456-24-6]2-Fluoro-5-nitropyridin</strong>e</strong> (52.35 g, 368 mmol, from step 12a) was combined with 5% Pd/C (100 mg) in EtOH (100 mL), and the mixture was stirred under a H2 atmosphere for 4 days. The mixture was filtered and concentrated, and the residue was chromatographed (silica gel;/EtOAc/hexane, 1:9 to 1:1) to afford 30.9 g (75%)of the title compound: 1 H NMR (DMSOd-6 300 MHz) delta6.74 (dd, J=3, 6 Hz, 1H), 7.11 (m, 1H), 7.26 (t, J=1 Hz, 1H); MS (CI/NH3) m/z: 113 (M+H)+, 130 (M+NH4)+.
30.9 g (75%)	palladium-carbon; In ethanol;	8c. 3-Amino-6-fluoropyridine <strong>[456-24-6]<strong>[456-24-6]2-Fluoro-5-nitropyridin</strong>e</strong> (52.4 g, 368 mmol, from Step 8b above) was combined with 5% Pd/C (100 mg, Aldrich) in EtOH (100 mL) and the mixture was stirred under a H2 atmosphere for 4 days. The mixture was filtered and concentrated. The crude product was chromatographed (silica gel; hexane/EtOAc, 9:1 to 1:1) to give 30.9 g (75%) of the title compound: 1 H NMR (DMSO-d6, 300 MHz) delta 6.74 (dd, J=3, 6 HzH, 1 H), 7.11 (m, 1 H), 7.26 (t, J=1 Hz, 1 H), MS (CI/NH3) m/z 113 (M+H)+, 130 (M+NH4)+.

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226.
[2]Patent: CN103755744,2016,B .Location in patent: Paragraph 0065; 0066.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1411 - 1416.
[4]Patent: US6355636,2002,B1 .Location in patent: Page column 64.
[5]Patent: EP1171440,2004,B1 .Location in patent: Page 53.
[6]Patent: US6313292,2001,B1 .
[7]Patent: US5733912,1998,A .
[8]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 481 - 484.
[9]Patent: US6133253,2000,A .

8
[ 4548-45-2 ]
[ 456-24-6 ]
[ 63913-20-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226.

Yield	Reaction Conditions	Operation in experiment
76%Spectr.	With tetramethylammonium fluoride; In N,N-dimethyl-formamide; at 20℃; for 24h;	General procedure: General Procedure E: General Experimental Details for NMR Yields Reported in Figure 3. In a drybox, anhydrous NMe4F (18.6 mg, 0.2 jumol, 2 equiv) and the appropriate aryi chloride or nitroarene substrate (0.1 nimol, 1 equiv) were weighed into a 4 mL vial equipped with a micro stirbar. DMF (0.5 mL) was added, and the viai was removed from the drybox and stirred at room temperature unless otherwise noted for 24 hours. The reaction was cooled to room temperature and an internal standard (1, 3, 5-trifluorobenzene, 100 iL of a 0.5 M solution in toluene) was added. An aliquot was removed for analysis by 59F NMR spectroscopy and GCMS.

11
[ 456-24-6 ]
sodium-salt of DL-phenylalanine [ No CAS ]
[ 36977-08-9 ]

References: [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1020,1024.

12
[ 456-24-6 ]
[ 438226-86-9 ]
[ 438226-87-0 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 5610 - 5611.

13
[ 372-48-5 ]
[ 456-24-6 ]

References: [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 538 - 541.

14
[ 456-24-6 ]
[ 67685-02-3 ]
[ 291-21-4 ]
S₃CH₂(CHCH)2(NH₂)2(C₆H₄OCH₂CH₂OC₂H₅)2(NC₅H₂NO₂)2 [ No CAS ]

References: [1]Organic Letters,2001,vol. 3,p. 1841 - 1843.

15
[ 141-86-6 ]
[ 456-24-6 ]
[ 863298-15-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	In dimethyl sulfoxide;	SYNTHESIS EXAMPLE 4 Synthesis of N-(5-amino-pyridin-2-yl)pyridine-2,6-diamine 2,6-Diaminopyridine (9.2 mmol, 1.0 g) and <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> (4.6 mmol, 0.65 g) were dissolved in 6 mL of DMSO. The solution was heated to 80° C. for 18 h. The solution eventually turned dark red. The reaction mixture was cooled to room temperature and purified directly by flash column chromatography (silica, EtOAc:Hexanes=1:3) to give N2-(5-nitropyridin-2-yl)pyridine-2,6-diamine as a reddish crystalline solid (0.21 g, 20percent yield): 1H NMR (500 MHz, CDCl3) delta 9.13 (d, 1H, J=3.0 Hz), 8.36 (dd, 1H, J=3.0 Hz, J2=9.5 Hz), 7.94 (d, 1H, J=9.5 Hz), 7.66 (s, 1H), 7.46 (t, 1H, J=8.0 Hz), 6.68 (d, 1H, J=8.0 Hz), 6.23 (d, 1H, J=8.0 Hz), 4.46 (s, 2H); Ms m/z (relative intensity) 232 (M+1, 100), 186 (57).

References: [1]Patent: US2005/188480,2005,A1 .

16
[ 456-24-6 ]
[ 108-45-2 ]
N-(5-nitro-[2]pyridyl)-m-phenylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In dimethyl sulfoxide;	SYNTHESIS EXAMPLE 5 Synthesis of N-(5-aminopyridin-2-yl)benzene-1,3-diamine m-Phenylenediamine (2.8 mmol, 0.30 g) and <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> (0.92 mmol, 0.13 g) were dissolved in 6 mL of DMSO. The solution was heated to 80° C. for 18 hours. The solution eventually turned dark red. The reaction mixture was cooled to room temperature and purified directly by flash column chromatography (silica, EtOAc:Hexanes=1:3) to give N1-(5-nitropyridin-2-yl)benzene-1,3-diamine as a reddish crystalline compound (0.19 g, 89percent yield): 1H NMR (500 MHz, CDCl3) delta 9.08 (d, 1H, J=2.5 Hz), 8.24 (dd, 1H, J1=2.5 Hz, J2=9.5 Hz), 7.281 (s, 1H), 7.19 (t, 1H, J=8.0 Hz), 6.82 (d, 1H, J=9.5 Hz), 6.74 (s, 1H), 6.70 (d, 1H, J=8.0 Hz), 6.56 (d, 1H, J=7.5 Hz), 3.80 (br, 2H); 13C NMR (125 MHz, CDCl3) delta 159.91, 148.05, 146.93, 139.09, 137.15, 133.59, 130.77, 112.80, 112.66, 109.13, 106.67.

References: [1]Patent: US2005/188480,2005,A1 .

17
[ 456-24-6 ]
[ 171178-41-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1411 - 1416.
[2]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226.

18
[ 456-24-6 ]
[ 171178-42-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1411 - 1416.
[2]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226.

19
[ 456-24-6 ]
[ 305371-18-0 ]