6635-91-2|6-Methoxy-4-methylpyridin-3-amine| Ambeed

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Quality Control of [ 6635-91-2 ] Purity: 98% SDS Specification

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Product Details of [ 6635-91-2 ]

CAS No. :	6635-91-2
Formula :	C₇H₁₀N₂O
M.W :	138.17
SMILES Code :	COC1=CC(C)=C(N)C=N1
MDL No. :	MFCD08277274
InChI Key :	PADDNCJJHROILV-UHFFFAOYSA-N
Pubchem ID :	243170

Safety of [ 6635-91-2 ]

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

Computational Chemistry of [ 6635-91-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	40.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.35
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	0.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.99
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.	0.28
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	1.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.6
Solubility	3.44 mg/ml ; 0.0249 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.	-1.43
Solubility	5.09 mg/ml ; 0.0368 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	-2.15
Solubility	0.974 mg/ml ; 0.00705 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.	-6.55 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	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)	1.73

Application In Synthesis of [ 6635-91-2 ]

* 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 [ 6635-91-2 ]

[ 6635-91-2 ] Synthesis Path-Downstream 1~35

1
[ 6635-90-1 ]
[ 6635-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 20℃; for 6h;	Reference Example 50 6-Methoxy-4-methylpyridin-3-amine A mixture of 2-methoxy-4-methyl-5-nitropyridine4-Methyl-5-nitro-2-pyrrolidin-1-ylpyridine (1.68 g, 10.0 mmol) and 10% palladium on carbon (168 mg) in tetrahydrofuran (10 mL) was stirred under hydrogen atmosphere at room temperature for 6 hr. Catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (1.31 g, 9.49 mmol, 95%) as a pale brown solid. 1H NMR (CDCl3) delta 2.16 (s, 3H), 3.28 (brs, 2H), 3.85 (s, 3H), 6.50 (s, 1H), 7.59 (s, 1H).

References: [1]Journal of the Chemical Society, <1954> 2448, 2451,.
[2]Patent: US2009/186879,2009,A1 .Location in patent: Page/Page column 59.

2
[ 6635-91-2 ]
[ 108-24-7 ]
[ 76013-32-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene; at 100℃; for 2h;	To a solution of <strong>[6635-91-2]6-methoxy-4-methylpyridin-3-amine</strong> (5.0 g, 36.2 mmol, 1.0 eq) in toluene (100.0 mL), was added acetic anhydride (5.2 g, 50.7 mmol, 1.4 eq). The mixture was stirred and heated at 100 C for 2 h, then cooled. The solvent of the mixture was removed in vacuo to provide N-(6-methoxy-4-methylpyridin-3-yl)acetamide (6.5 g, 100%).

References: [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00631.
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404.

3
[ 6635-91-2 ]
[ 76006-07-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404.
[2]Patent: WO2018/11628,2018,A1 .

4
[ 6635-91-2 ]
[ 76006-02-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404.
[2]Patent: WO2018/11628,2018,A1 .

5
[ 6635-91-2 ]
[ 76006-03-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2398 - 2404.

6
tin(II)chloride dihydrate [ No CAS ]
[ 6635-90-1 ]
[ 6635-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In acetic acid;	b 5-Amino-2-methoxy-4-methylpyridine A mixture of stannous chloride dihydrate (41 g) and concentrated hydrochloric acid (40 ml) was added slowly to a solution of 2-methoxy-4-methyl-5-nitropyridine (5.1 g) in acetic acid (40 ml), maintaining the temperature below 35 C. The resulting mixture was stirred at room temperature for 2 hours, and then allowed to stand overnight in the refrigerator. The solid was collected and both solid and supernatant were separately basified with a 20% sodium hydroxide solution. The product was extracted with chloroform, combined, dried (anhydrous magnesium sulfate) and concentrated to give 3.9 g of the title compound as a solid, suitable for use in the next reaction.

References: [1]Patent: US5366972,1994,A .

7
[ 6635-91-2 ]
[ 135795-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; sodium acetate; In water; acetic acid;	c 3-Amino-2-bromo-6-methoxy-4-methylpyridine Bromine (4.8 g) was added in one portion to a mixture of <strong>[6635-91-2]5-amino-2-methoxy-4-methylpyridine</strong> (3.9 g) in acetic acid (25 ml) and sodium acetate (4.0 g). The resulting mixture was stirred for 20 min. and then added to a solution of sodium hydroxide (15 g) in water (200 ml). The product was extracted with chloroform, dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (methylene chloride/ethyl acetate, 19:1?4:1) to give 4.5 g of the title compound, suitable for use in the next reaction.

References: [1]Patent: US5366972,1994,A .

8
[ 6635-91-2 ]
[ 1173983-06-6 ]
[ 1173983-20-4 ]

Yield	Reaction Conditions	Operation in experiment
10%		Reference Example 51 Ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(6-methoxy-4-methylpyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 1.50 g, 4.04 mmol), <strong>[6635-91-2]6-methoxy-4-methylpyridin-3-amine</strong> (1.10 g, 8.09 mmol) and p-toluenesulfonic acid monohydrate (487 mg, 2.83 mmol) in 1-methyl-2-pyrrolidinone (8 mL) was irradiated by microwave at 180 C. for 10 min. After cooling, the mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluding with a 20-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give an amorphous which was recrystallized from ethyl acetate/n-hexane to give the title compound (190 mg, 0.402 mmol, 10%) as a colorless solid. mp 140-142 C. 1H NMR (CDCl3) delta 0.86 (t, J=7.3 HZ, 6H), 1.27 (t, J=7.2 Hz, 3H), 1.65-1.89 (m, 4H), 2.02-2.23 (m, 2H), 2.32 (s, 3H), 2.41-2.56 (m, 2H), 2.87-3.02 (m, 1H), 3.92 (s, 3H), 4.10-4.29 (m, 4H), 6.63 (s, 1H), 6.83 (d, J=8.3 Hz, 1H), 7.11 (d, J=8.7 Hz, 1H), 7.13 (s, 1H), 8.43 (s, 1H). MS Calcd.: 472; Found: 473 (M+H).

References: [1]Patent: US2009/186879,2009,A1 .Location in patent: Page/Page column 59.

9
[ 6635-91-2 ]
[ 1419608-63-1 ]

References: [1]Patent: WO2013/12500,2013,A1 .

10
[ 6635-91-2 ]
[ 1419610-12-0 ]

References: [1]Patent: WO2013/12500,2013,A1 .

11
[ 6635-91-2 ]
1-(((5S,7S)-7-methyl-3-(4-methyl-6-morpholinopyridin-3-yl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile [ No CAS ]

References: [1]Patent: WO2013/12500,2013,A1 .

12
[ 6635-91-2 ]
[ 1419610-78-8 ]

References: [1]Patent: WO2013/12500,2013,A1 .

13
[ 6635-91-2 ]
[ 1419610-77-7 ]

References: [1]Patent: WO2013/12500,2013,A1 .

14
[ 6635-91-2 ]
[ 541-41-3 ]
[ 1419610-66-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 0℃; for 1h;	Ethyl r4-methyl-6-(methyloxy)-3-pyridinvHcarbamateTo a 100 mL flask was added <strong>[6635-91-2]4-methyl-6-(methyloxy)-3-pyridinamine</strong> (850 mg, 6.15 mmol), pyridine (10 mL) and then ethyl chloroformate (0.650 mL, 6.77 mmol) portionwise. The reaction mixture was stirred for 1 h at 0 C. The reaction mixture was then concentrated and partitioned between ammonium chloride and DCM, and the aqueous layer was extracted with DCM (2x). The combined organics layers were washed with brine (1x), eluted through a phase separator then concentrated to afford ethyl [4-methyl-6-(methyloxy)-3-pyridinyl]carbamate (1.223 g, 90 % yield).

References: [1]Patent: WO2013/12500,2013,A1 .Location in patent: Page/Page column 82.

15
[ 6635-91-2 ]
[ 24424-99-5 ]
[ 221675-30-5 ]

Yield	Reaction Conditions	Operation in experiment
8.8 g	With sodium carbonate; In tetrahydrofuran; water;	To a solution of <strong>[6635-91-2]5-amino-2-methoxy-4-picoline</strong> (5.0 g, 36.2 mmol) in THF (80 mL) and saturated aqueous Na2003 (20 mL) was added di-tert-butyl-dicarbonate (7.9 g, 36.2 mmol) and the reaction mixture was stirred overnight. The reaction mixture was concentrated, extracted with DCM, washed with brine, dried, filtered and the solvent evaporated to afford the title compound(8.8 g). MS: [M+H] = 239.

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7314 - 7329.
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1843 - 1850.
[3]Patent: WO2015/92420,2015,A1 .Location in patent: Page/Page column 128.

16
[ 6635-91-2 ]
2-(5-((tert-butoxycarbonyl)amino)-2-methoxypyridin-4-yl)acetic acid [ No CAS ]

References: [1]Patent: WO2015/92420,2015,A1 .
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1843 - 1850.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 7314 - 7329.

17
[ 6635-91-2 ]
5-methoxy-2-oxo-2,3-dihydro-pyrrolo[2,3-c] pyridine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Patent: WO2015/92420,2015,A1 .
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1843 - 1850.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 7314 - 7329.

18
[ 6635-91-2 ]
C₈H₇ClINO [ No CAS ]
1-(2-iodophenyl)-3-(6-methoxy-4-methylpyridin-3-yl)-1-methylurea [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9168 - 9172.
Angew. Chem.,2016,vol. 128,p. 9314 - 9318,5.

19
[ 6635-91-2 ]
3-(6-methoxy-4-methylpyridin-3-yl)-1-methyl-1-(2-(phenylethynyl)phenyl)urea [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9168 - 9172.
Angew. Chem.,2016,vol. 128,p. 9314 - 9318,5.

20
[ 6635-91-2 ]
10-methoxy-5,8-dimethyl-12-phenylpyrido[2',3':4,5]pyrrolo[1,2-c]quinazolin-6(5H)-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9168 - 9172.
Angew. Chem.,2016,vol. 128,p. 9314 - 9318,5.

21
[ 6635-91-2 ]
[ 143875-94-9 ]
3,4-dihydro-4-imino-3-(6-methoxy-4-methylpyridin-3-yl)-1-methylquinazolin-2(1H)-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 587 - 590.
Angew. Chem.,2017,vol. 129,p. 602 - 605,4.

22
[ 6635-91-2 ]
[ 143875-94-9 ]
10-methoxy-5,8-dimethylpyrido[2',3':4,5]imidazo[1,2-c]quinazolin-6(5H)-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 587 - 590.
Angew. Chem.,2017,vol. 129,p. 602 - 605,4.

23
[ 6635-91-2 ]
6-(4-chlorobenzyl)-3,3-diethyl-1-methyl-1H-pyrrolo[2,3-c]pyridine-2,5(3H,6H)-dione [ No CAS ]