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Quality Control of [ 1060806-62-3 ] Purity: 95% SDS Specification

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Product Details of [ 1060806-62-3 ]

CAS No. :	1060806-62-3
Formula :	C₇H₆BrNO₃
M.W :	232.03
SMILES Code :	O=C(O)C1=C(OC)N=C(Br)C=C1
MDL No. :	MFCD13188730
InChI Key :	YMPQUJFCCCPCAF-UHFFFAOYSA-N
Pubchem ID :	71303922

Safety of [ 1060806-62-3 ]

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

Calculated chemistry of [ 1060806-62-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	45.39
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.42 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
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	1.71
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.	-0.2
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	1.41
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.59
Solubility	0.591 mg/ml ; 0.00255 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.57
Solubility	0.62 mg/ml ; 0.00267 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	-2.39
Solubility	0.954 mg/ml ; 0.00411 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.	-6.5 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	0.0
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	1.0 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)	1.89

Application In Synthesis of [ 1060806-62-3 ]

* 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 [ 1060806-62-3 ]

[ 1060806-62-3 ] Synthesis Path-Downstream 1~11

1
[ 1060806-62-3 ]
[ 74-88-4 ]
[ 1009735-24-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	Step 2: <strong>[1060806-62-3]6-bromo-2-methoxy-nicotinic acid</strong> methyl ester; To potassium carbonate (1.34 g, 9.48 mmol) in N,N-dimethylformamide (10 mL) was added <strong>[1060806-62-3]6-bromo-2-methoxy-nicotinic acid</strong> (1.10 g, 4.74 mmol) and methyl iodide (0.895 g, 6.31 mmol). The reaction was stirred for 16 h at room temperature. The reaction mixture was diluted with water and ethyl acetate, the layers were separated. The aqueous layer was washed with ethyl acetate 2 times. The combined organic layers were washed with brine and dried over magnesium sulfate, filtered and concentrated. The filtrate was concentrated and purified by silica gel column chromatography eluting with a gradient of 5% - 10% ethyl acetate/ heptane to obtain the title compound as a colorless oil (0.459 g, 40%). 1 H NMR (500 MHz, DMSO-d6) delta ppm 3.81 (3 H, s), 3.93 (3 H, s), 7.36 (1 H, d, J=7.8 Hz), 8.06 (1 H, d, J=7.8 Hz).

References: [1]Patent: WO2010/116282,2010,A1 .Location in patent: Page/Page column 60.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4273 - 4288.

2
[ 40473-07-2 ]
[ 124-38-9 ]
[ 1060806-62-3 ]

Yield	Reaction Conditions	Operation in experiment
42.9%		Preparation 21 : 2-methoxy-6-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- nicotinamide; Step 1 : theta-bromo^-methoxy-nicotinic acid; A solution of 2,2,6,6-tetramethylpiperidine (0.766 g, 5.32 mmol) in tetrahydrofuran (5 mL) was cooled to -78C under nitrogen. 2.5M n-butyllithium in hexanes (2.34 ml_, 0.375 g, 5.85 mmol) and the mixture was stirred at -780C for 30 min. To the reaction mixture was added a solution of 2-bromo-6-methoxypridine (1.00 g, 5.32mmol) in tetrahydrofuran (5 mL) dropwise. The reaction was stirred at -78C for 1 h. After this time, an excess of dry ice was added to the reaction mixture and the reaction was allowed to warm to room temperature for 3 h. To the mixture was added water and ethyl acetate, the layers were separated. The aqueous layer was acidified to pH 4. The aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to an off-white solid (0.530 g, 42.9 %) 1 H NMR (500 MHz, DMSO-d6) delta ppm 2.52 (2 H, br. s.), 3.32 (1 H, br. s.), 3.92 (1 H, m), 3.90 (1 H, d, J=2.9 Hz), 8.03 (1 H, d, J=7.8 Hz).

References: [1]Patent: WO2010/116282,2010,A1 .Location in patent: Page/Page column 60.

3
[ 1060806-62-3 ]
[ 1448449-27-1 ]

References: [1]Tetrahedron Letters,2013,vol. 54,p. 4515 - 4517.

4
[ 1060806-62-3 ]
[ 1448449-28-2 ]

References: [1]Tetrahedron Letters,2013,vol. 54,p. 4515 - 4517.

5
[ 1060806-62-3 ]
[ 785807-22-9 ]

References: [1]Tetrahedron Letters,2013,vol. 54,p. 4515 - 4517.

6
[ 69016-02-0 ]
[ 1060806-62-3 ]
[ 1448449-26-0 ]

Yield	Reaction Conditions	Operation in experiment
58%		To a solution of2,2,6,6-tetramethylpiperidine(3.6 g,25.6 mmol) in anhydrous THF (50 mL) was added n-BuLi (2.5 Min n-hexane, 11.2 mL, 28 mmol) at -78 C under nitrogen. The mixture wasstirred for 30 min before <strong>[1060806-62-3]6-bromo-2-methoxynicotinic acid</strong> (2, 1.5 g,6.4 mmol) was added. After the mixture was stirred for 30 min at -78 C, ketone amide 3 (3.0 g, 19mmol) was added and the mixture stirred for another 30 min. Then the mixturewas allowed to reach room temperature and diluted with water (100 mL) andextracted with ethyl acetate (30 mL). Theaqueous layer was treated with 1 N HCl (20 mL) and extracted with ethyl acetate. The organic layer was washed withbrine, dried over anhydrous Na2SO4, and concentratedunder reduced pressure. The residue was purified by trituration with petrolether (20 mL) to give bromide 4 (1.4 g, yield 58%) as a white solid. 1HNMR (400MHz, CDCl3) delta 7.61 (s, 1H), 4.09 (s, 3H), 3.90 (qd, J=14.0, 6.8 Hz, 1H), 3.47 (qd, J= 13.4, 6.8 Hz, 1H), 3.20 (qd, J=14.3, 6.8 Hz, 1H), 3.09 (qd, J= 13.5, 6.7 Hz, 1H), 2.31 (qd, J=14.5, 7.3 Hz, 1H), 2.05 (qd, J= 14.4, 7.3 Hz, 1H), 1.18 (t, J=6.8 Hz, 3H), 1.09 (t, J= 6.8 Hz, 3H), 0.80 (t, J= 7.4 Hz, 3H). 13C NMR (100 MHz, CDCl3)d 166.1, 165.5,164.5, 159.8, 144.9, 117.9, 106.7, 89.3, 55.2, 42.6, 42.5, 32.1, 14.6, 12.2,7.5. HRMS (ESIMS) calcd for C15H19BrN2O4[M + H] + 371.0601, found 371.0589.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 4515 - 4517.

7
[ 1060806-62-3 ]
[ 1246765-36-5 ]