211915-96-7|Methyl 5-amino-6-chloronicotinate| Ambeed

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Quality Control of [ 211915-96-7 ] Purity: 95% SDS Specification

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Product Details of [ 211915-96-7 ]

CAS No. :	211915-96-7
Formula :	C₇H₇ClN₂O₂
M.W :	186.60
SMILES Code :	O=C(OC)C1=CN=C(Cl)C(N)=C1
MDL No. :	MFCD02180841
InChI Key :	BENHZYFIGMDHEB-UHFFFAOYSA-N
Pubchem ID :	18412438

Safety of [ 211915-96-7 ]

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

Computational Chemistry of [ 211915-96-7 ] 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	3.0
Num. H-bond donors	1.0
Molar Refractivity	44.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.21 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.54
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	0.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.11
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.	0.35
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	1.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.86
Solubility	2.58 mg/ml ; 0.0138 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.	-1.95
Solubility	2.1 mg/ml ; 0.0113 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	-2.36
Solubility	0.815 mg/ml ; 0.00437 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.	-6.74 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	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)	1.77

Application In Synthesis of [ 211915-96-7 ]

* 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 [ 211915-96-7 ]

[ 211915-96-7 ] Synthesis Path-Downstream 1~35

1
[ 211915-96-7 ]
[ 38870-89-2 ]
[ 211915-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorobenzene; Petroleum ether;	b Methyl 6-chloro-5-methoxyacetamido-nicotinate A solution of 0.75 g (4.02 mMol) of <strong>[211915-96-7]methyl 5-amino-6-chloro-nicotinate</strong> and 0.43 g=0.35 ml (4.5 mMol) of methoxyacetylchloride in 20 ml of chlorobenzene was stirred for one hour at 110 C. After the solvent had been removed in vacuo the crude product obtained was purified by flash chromatography (silica gel; methylene chloride/ethanol=100:1), evaporated down again in vacuo and then digested with petroleum ether. Yield: 0.55 g (53% of theory) light yellow amorphous solid, Rf value: 0.33 (silica gel; ethyl acetate/petroleum ether=1:4)

References: [1]Patent: US6087380,2000,A .

2
[ 59237-53-5 ]
[ 7439-89-6 ]
[ 211915-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; water;	a Methyl 5-amino-6-chloro-nicotinate A solution of 1.08 g (5.00 mMol) of methyl 6-chloro-5-nitro-nicotinate (see A. H. Berrie, G. T. Newbold, F. S. Spring in J. Chem. Soc., 2590, 1951) in 25 ml of absolute ethanol was mixed successively with 0.53 ml (29 mmol) of water, 3.2 g (57 mMol) of iron powder and 0.030 ml of concentrated hydrochloric acid and heated to boiling for one hour. Then equal quantities of water, iron powder and hydrochloric acid were added and the mixture was heated to boiling for 30 minutes. The precipitate formed on cooling was filtered off and washed with ethanol and the solvent was distilled off in vacuo. Yield: 0.75 g (81percent of theory) of greenish-yellow solid, Rf value: 0.31 (silica gel;ethyl acetate/petroleum ether=1:4) C7 H7 ClN2 O2 (186.60) YEF- Mass spectrum: M+ =186 and 188 (chlorine isotopes).

References: [1]Patent: US6087380,2000,A .

3
[ 211915-96-7 ]
[ 463-71-8 ]
[ 936247-04-0 ]

Yield	Reaction Conditions	Operation in experiment
76.1%	With sodium carbonate; In dichloromethane; at 20℃; for 4h;	Step A: Preparation of methyl 6-chloro-5- isothiocyanatonicotinate :; Thiophosgene (6.367 g, 55.37 mmol) in dichloromethane (10 niL) was added to a mixture of methyl 5-amino-6- chloronicotinate (8.61 g, 46.14 mmol) and sodium carbonate (9.781 g, 92.29 mmol) in dichloromethane (200 mL). The reaction mixture was stirred for four days at ambient temperature. The reaction mixture was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 12:1 hexane:ethyl acetate to afford methyl 6-chloro-5- isothiocyanatonicotinate (8.03 g, 76.1% yield) as a white solid: 1H NMR (CDCl3) delta 3.97 (s, 3H)5 8.09 (s, IH), 8.84 (s, IH).

References: [1]Patent: WO2007/53345,2007,A1 .Location in patent: Page/Page column 149.

4
[ 211915-96-7 ]
[ 610-14-0 ]
[ 1231952-69-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; In dichloromethane; at 20℃; for 10h;	Pyridine (1.1 eq) was added to a solution of methyl 5-amino-6- chloronicotinate (1 eq) and 2-nitrobenzoyl chloride (1.2 eq) in CH2Cl2. The mixture was stirred at room temperature for 1Oh and concentrated in vacuo. H2O was added and the resultant solid was collected by filtration, rinsed with CH2Cl2 and dried to give methyl 6-chloro-5-(2-nitrobenzamido)nicotinate (73 % yield)

References: [1]Patent: WO2010/71853,2010,A1 .Location in patent: Page/Page column 68; 69.

5
[ 59237-53-5 ]
[ 211915-96-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With iron; ammonium chloride; In methanol; at 75℃; for 2h;	A suspension of methyl beta-chloro-S-nitronicotinate (1 eq), iron powder (5.2 eq), and NH4Cl3 (5.3 eq) in MeOH was heated at 75°C for 2 h. The mixture was passed through a pad of celite while hot and concentrated in vacuo to give methyl 5- amino-6-chloronicotinate (56 percent yield)
	With stannous chloride; In methanol; for 18h;Inert atmosphere; Reflux;	Part I - Synthesis of methyl 5-amino-6-chloronicotinate [0290] To methyl 6-chloro-5-nitro-pyridine-3-carboxylate (2.0 g, 9.2 mmol) in anhydrous methanol (30 mL) under nitrogen was added tin (II) chloride (5.3 g, 28 mmol). The resulting mixture was refluxed for 18 hours. Then, the reactiom mixture was cooled and then poured carefully into a stirred slurry of celite in saturated sodium bicarbonate at 0°C. The resulting suspension was stirred for 20 minutes before filtering the mixture through celite to remove the solids. The solids were washed with ethyl acetate, and the filtrates were collected, washed with water, and washed with brine. The resulting organic solution was dried with sodium sulfate, filtered, and concentrated in vacuo to provide the title compound as a crude mixture. (1.7 g, 92percent yield); HPLC retention time Method A: 2.99 minutes (91.8percent pure).
	With tin(ll) chloride; In methanol; for 18h;Inert atmosphere; Reflux;	Part I - Synthesis of methyl 5-amino-6-chloronicotinate [0378] To methyl 6-chloro-5-nitro-pyridine-3-carboxylate (2.0 g, 9.2 mmol) in anhydrous methanol (30 mL) under nitrogen was added tin (II) chloride (5.3 g, 28 mmol). The resulting mixture was refluxed for eighteen hours. Then, the reaction mixture was cooled and then poured carefully into a stirred slurry of CELITE in saturated sodium bicarbonate at 0 °C. The resulting suspension was stirred for twenty minutes before the mixture was filtered through CELITE to remove the solids. The solids were washed with ethyl acetate, and the filtrates were collected, washed with water, and washed with brine. The resulting organic solution was dried with sodium sulfate (Na2S04) and concentrated to provide the title compound.

References: [1]Patent: WO2010/71853,2010,A1 .Location in patent: Page/Page column 68.
[2]Patent: WO2013/169704,2013,A2 .Location in patent: Paragraph 0290.
[3]Patent: WO2015/95795,2015,A1 .Location in patent: Paragraph 0378.

6
[ 211915-96-7 ]
methyl 5-(3-methylphenylsulfonamido)-6-vinylnicotinate [ No CAS ]