202217-19-4|6-Chloro-5-methyl-3-nitropyridin-2-amine| Ambeed

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Quality Control of [ 202217-19-4 ] Purity: 97% SDS Specification

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Product Details of [ 202217-19-4 ]

CAS No. :	202217-19-4
Formula :	C₆H₆ClN₃O₂
M.W :	187.58
SMILES Code :	CC1=C(Cl)N=C(N)C(=C1)[N+]([O-])=O
MDL No. :	MFCD17014970
InChI Key :	VXAQCLXAYGVVBB-UHFFFAOYSA-N
Pubchem ID :	21837379

Safety of [ 202217-19-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 202217-19-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	47.44
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.73 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.13
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	2.21
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.54
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.	0.06
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	-0.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.91

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.7
Solubility	0.375 mg/ml ; 0.002 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.	-3.62
Solubility	0.0446 mg/ml ; 0.000238 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	-2.05
Solubility	1.66 mg/ml ; 0.00887 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	Yes
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.	-5.88 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)	2.22

Application In Synthesis of [ 202217-19-4 ]

* 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.

Downstream synthetic route of [ 202217-19-4 ]

[ 202217-19-4 ] Synthesis Path-Downstream 1~25

1
[ 58596-88-6 ]
[ 202217-19-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With ammonia; potassium carbonate; In water; tert-butyl alcohol; at 20 - 60℃;	(2e) 6-Chloro-5-methyl-3-nitro-2-pyridinamine [Formula 22]; A mixture of 2,6-dichloro-3-methyl-5- nitropyridine (10.41 g, 50.3 mmol), 28% aqueous ammonia solution (17 ml, 0.25 mol), potassium carbonate (10.4 g, 75.5 mmol) and t-butanol (167 ml) was stirred overnight at 60C under nitrogen atmosphere. After stirring at room temperature for 3 hours, a precipitate was filtered and then washed three times with water, thereby yielding the title compound (4.25 g, 22.7 mmol, 45%) as a yellow solid. ¹H NMR(400MHz, QMSO-D6) No. ppm; 2.23,(3H, s), 8.04(2H, br s), 8.39(1H, s).

References: [1]ChemMedChem,2019,vol. 14,p. 952 - 964.
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4512 - 4522.
[3]Patent: WO2005/103049,2005,A1 .Location in patent: Page/Page column 73-74.

2
[ 202217-19-4 ]
[ 359-13-7 ]
[ 868539-31-5 ]

Yield	Reaction Conditions	Operation in experiment
96%		Example 3; 5- (2,2-Difluoroethoxy)-2-(((4-methoxy-3- methyl-2-pyridinyl) methyl)sulfinyl)-6-methyl-3H- imidazo [4,5-b]pyridine Sodium salt [Formula 28]; (3a) 6-(2,2-difluoroethoxy)-5-methyl-3-nitro-2- pyridineamine [Formula 29]; 2,2-Difluoro ethanol (418 mg, 5.1 mmol) was dissolved in tetrahydrofuran (15 ml), sodium hydride (60%) '(180 mg, 4.5 mmol) was added thereto under nitrogen atmosphere, and the reaction mixture was stirred for 30 minutes at room temperature. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine (600 mg, 3.20 mmol) in tetrahydrofuran (15 ml) was dropped, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution and extracted with ethyl acetate, and after washed with sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was triturated with n-hexane to yield the'title compound (685 mg, 3.1 mmol, 96%) as an orange solid. ¹H NMR(400MHz, DMSO-d6) No. ppm; 2.05 (3H, s) , 4.56- 4.69 (2H, m), 6.29-6.60(1H, m), 8.03 (2H, s), 8.19(lH, s) .

References: [1]Patent: WO2005/103049,2005,A1 .Location in patent: Page/Page column 79-80.

3
[ 202217-19-4 ]
[ 75-89-8 ]
[ 868539-26-8 ]

Yield	Reaction Conditions	Operation in experiment
		(2f) 5-Methyl-3-nitro-6-(2,2,2-trifluoroethoxy)-2- pyridinamine [Formula 23]; 2,2,2-Trifluoroethanol (340 mg, 3.4 mmol) was dissolved in the tetrahydrofuran (10 ml), sodium hydride (60%) (120 mg, 3.0 mmol) was added thereto, and the reaction mixture was stirred for 30 minutes at room temperature under nitrogen atmosphere. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine crude product (400 mg) in tetrahydrofuran (10 ml) was dropped, and the reaction mixture was stirred at room temperature for 2.5 days. Water was added to the' reaction solution and extracted with ethyl acetate, and after washed with a sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n- hexane= 15/85) to yield the title compound (225 mg, 0.90 mmol) as a yellow solid. (at)H NMR (400MHz, DMSO-d6) No. ppm; 2.07 (3H, s), 5.06 (2H, J=9Hz), 8.05 (2H, s), 8.24(1H, s).

References: [1]Patent: WO2005/103049,2005,A1 .Location in patent: Page/Page column 74-75.

4
[ 18368-64-4 ]
[ 202217-19-4 ]