73177-35-2|2-Methyl-1H-pyrrolo[3,2-b]pyridine| Ambeed

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Quality Control of [ 73177-35-2 ] Purity: 97% SDS Specification

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Product Details of [ 73177-35-2 ]

CAS No. :	73177-35-2
Formula :	C₈H₈N₂
M.W :	132.16
SMILES Code :	CC1=CC2=NC=CC=C2N1
MDL No. :	MFCD12923706
InChI Key :	FTDBLXOLABKXNQ-UHFFFAOYSA-N
Pubchem ID :	11586310

Safety of [ 73177-35-2 ]

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

Computational Chemistry of [ 73177-35-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	41.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.42
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	1.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.87
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.	0.91
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	2.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.741 mg/ml ; 0.0056 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.	-1.68
Solubility	2.77 mg/ml ; 0.0209 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	-3.26
Solubility	0.0721 mg/ml ; 0.000546 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	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.	-6.06 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)	1.39

Application In Synthesis of [ 73177-35-2 ]

* 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 [ 73177-35-2 ]

[ 73177-35-2 ] Synthesis Path-Downstream 1~35

1
[ 6298-19-7 ]
[ 67-64-1 ]
[ 73177-35-2 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 1943 - 1944.
[2]Tetrahedron Letters,1980,vol. 21,p. 1943 - 1944.
[3]Journal of Organic Chemistry,1980,vol. 45,p. 1546 - 1547.
[4]Heterocycles,1981,vol. 16,p. 1473 - 1474.

2
[ 56983-98-3 ]
[ 110-86-1 ]
[ 100-69-6 ]
[ 109-06-8 ]
[ 100-71-0 ]
[ 73177-35-2 ]
[ 4916-40-9 ]

References: [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 4352 - 4358.

3
<i>N</i>-<2-methyl-<3>pyridyl-diacetamide [ No CAS ]
[ 73177-35-2 ]

References: [1]Journal of the Chemical Society,1948,p. 198.

4
[ 73177-35-2 ]
[ 89-75-8 ]
[ 219762-87-5 ]

Yield	Reaction Conditions	Operation in experiment
		In the same manner as in Preparation Example 16-2, the objective compound (1.23 g) was obtained as a colorless solid from <strong>[73177-35-2]2-methylpyrrolo[3,2-b]pyridine</strong> (500 mg). 1H-NMR(DMSO-d6): 2.75(3H, s), 7.07(1H, dd, J=8, 5 Hz), 7.38(1H, d, J=8 Hz), 7.48(1H, d, J=8 Hz), 7.65(1H, s), 7.74(1H, d, J=8 Hz), 8.14(1H, d, J=5 Hz). MASS(ESI): m/z 303(M-1)

References: [1]Patent: US6348474,2002,B1 .Location in patent: Page column 59,60.

5
[ 1383924-63-7 ]
[ 73177-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium hydroxide; at 80℃; for 1.5h;	2-methyl-l H-py rrolo [3,2-b] pyridine; [00365] To a 10 C solution of 2-chloropyridin-3 -amine (2.00 g, 15.6 mmol) in 1,4- dioxane (20. mL) was added an aqueous solution of 1M sodium hydroxide (31.2 mL, 31.2 mmol). To this reaction mixture was added ethyl chloroformate (1.80 mL, 18.7 mmol), and the reaction was warmed to room temperature. After 2 hours, an additional ethylchloroformate (0.8 mL) was added, and the reaction was stirred at room temperature for 12 hours, after which it was complete by LCMS analysis. The reaction mixture was diluted in water (50 mL), extracted with ethyl acetate (3 x 50 mL), washed with saturated sodium chloride solution (1 x 50 mL), dried (sodium sulfate), filtered and concentrated to afford a yellow oil which was purified on silica gel (ISCO 80g, 20 mL/min ) using 15% ethyl acetate in hexanes over 60 minutes. Ethyl 2-chloropyridin-3-yl carbamate (2.21 g, 11.0 mmol, 71 % yield) was isolated as a white solid. NMR (400 MHz, CDC13) a (ppm): 8.51 (d, 1H), 8.07 (dd, 1H), 7.23-7.27 (m, 1H), 7.13 (br. s, 1H), 4.28 (q, 2H), 1.34 (t, 3H).[00366] To a suspension of lithium chloride (341 mg, 8.05 mmol) in 1,4-dioxane (16.4 mL) was added ethyl 2-chloropyridin-3-yl carbamate (660 mg, 3.29 mmol), tributyl(prop-l- ynyl)stannane (1.00 mL, 3.29 mmol) and Pd(Ph3P) (76.0 mg, 0.0660 mmol). The mixture was refluxed for 1.5 hours, after which the reaction showed >75% product with some starting material remaining. The reaction was continued heating for 12 hours (overnight), after which it was cooled, diluted with water, extracted with ethyl acetate (3 x 50 mL), washed with saturated aqueous sodium hydrogen carbonate solution (3 x 50 mL), followed by brine (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography (Luknova 120g, 20 mL/min) using 10 to 60% ethyl acetate in hexanes over 60 minutes affording ethyl 2-(prop-l-ynyl)pyridin-3-ylcarbamate (420 mg, 2.06 mmol, 63 % yield) as a gold oil. NMR (400 MHz, CDC13) a (ppm): 8.45 (d, 1H), 8.21 (dd, 1H), 7.34 (br. s, 1H), 7.21 (dd, 1H), 4.27 (q, 2H), 2.19 (s, 3H), 1.34 (t, 3H).[00367] To a solution of ethyl 2-(prop- 1 -ynyl)pyridin-3-ylcarbamate (400 mg, 1.96 mmol) in absolute ethanol (653 mu) was added solid sodium hydroxide (400 mg, 5.88 mmol). The reaction was heated to 80 C for 1.5 hours, after which the reaction mixture was cooled, diluted in water, extracted with dichloromethane (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a pink solid. This solid was isolated -90% pure as 2 -methyl- 1H- pyrrolo[3,2-b]pyridine (250 mg, 1.70 mmol, 87 % yield), and used without further purification in the next step. NMR (400 MHz, CDC13) a (ppm): 8.39 (dd, 1H), 8.22 (br. s, 1H), 7.55 (d, 1H), 7.02 (dd, 1H), 6.44 (s, 1H), 2.51 (s, 3H).
	With sodium ethanolate; In ethanol; for 1.5h;Heating / reflux;	Preparation Example 25-3 2-Methylpyrrolo[3,2-b]pyridine To a solution of ethyl-2-(1-propyn-1-yl)-3-pyridyl carbamate (10.9 g) in ethanol was added a 21% solution (50 ml) of sodium ethylate in ethanol and the mixture was refluxed under heating.. After 1.5 hr, the reaction mixture was cooled and water was added, which was followed by three times of extraction with dichloromethane.. The organic layer was dried over anhydrous magnesium sulfate, and filtrated.. The filtrate was concentrated and the residue was crystallized from ethyl acetate to give the objective compound (6.5 g) as pale-brown crystals. 1H-NMR(CDCl3): 2.41(3H, s), 6.23(1H, s), 6.97(1H, dd, J=8, 5 Hz), 7.60(1H, d, J=8 Hz), 8.19(1H, br d, J=5 Hz) MASS(ESI): m/z 133(M+1) mp 193-195 C.

References: [1]Patent: WO2012/88469,2012,A1 .Location in patent: Page/Page column 149-150.
[2]Patent: US6348474,2002,B1 .Location in patent: Page column 59.

6
[ 6298-19-7 ]
[ 73177-35-2 ]

References: [1]Patent: WO2012/88469,2012,A1 .
[2]Patent: US6348474,2002,B1 .

7
[ 73177-35-2 ]
[ 1383924-42-2 ]

References: [1]Patent: WO2012/88469,2012,A1 .

8
[ 73177-35-2 ]
[ 1383922-54-0 ]

References: [1]Patent: WO2012/88469,2012,A1 .

9
[ 73177-35-2 ]
[ 104-83-6 ]
[ 1383924-41-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium hydroxide; In dimethyl sulfoxide; at 20℃; for 12h;	Example 2 (see general route 2, procedure E, F, C and D)2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2-methoxypyridin- 4-yl)-2-oxoacetamide (3) [00252] To a solution of 2-methyl-lH-pyrrolo[3,2-b]pyridine (74.4 mg, 0.563 mmol) and 4-chlorobenzyl chloride (0.0780 mL, 0.619 mmol) in DMSO (8 mL) at room temperature was added powdered potassium hydroxide (69.5 mg, 1.24 mmol). The reaction was stirred at room temperature for 12 hours, after which LCMS analysis indicated that the reaction was complete. The reaction mixture was diluted in water and extracted with dichloromethane (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a clear residue. Purification was achieved by silica gel chromatography using 30 to 90% ethyl acetate in hexanes over 80 minutes affording l-(4-chlorobenzyl)-2 -methyl- lH-pyrrolo[3,2-b]pyridine (64.2 mg, 0.250 mmol, 44% yield) as an off-white solid. NMR (400 MHz, CDC13) delta (ppm): 8.41 (dd, 1H), 7.41 (d, 1H), 7.24 (d, 2H), 7.01 (dd, 1H), 6.86 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.41 (s, 3H).[00253] To a solution of l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridine (341 mg, 1.33 mmol) in dichloromethane (25 mL) was added aluminum trichloride (886 mg, 6.65 mmol). The mixture was stirred at room temperature for 20 minutes, after which ethyl oxalyl chloride (0.744 mL, 6.65 mmol) was added. The reaction mixture was stirred at room temperature for an additional three hours, after which it was poured over ice and extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate) filtered and concentrated to afford 2-(l- (4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetic acid (76.5 mg, 0.233 mmol, 18% yield) an off-white solild. This material was used without any purification in the next step. The intended product of this reaction, ethyl 2-(l-(4-chlorobenzyl)-2-methyl-lH- pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetate, was observed in trace amounts and was not isolated from the reaction mixture. NMR (400 MHz, CDC13) delta (ppm): 8.44 (dd, 1H), 7.41 (dd, 1H), 7.20 (d, 2H), 7.04 (dd, 1H), 6.84 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.77 (s, 3H)[Carboxylic acid proton not detected in 1H NMR]. LCMS: 2.18 min, [ES]" found 327.10.[00254] To a solution of 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3- yl)-2-oxoacetic acid (76.5 mg, 0.218 mmol) in acetonitrile (7 mL) was added triethylamine (0.304 mL, 2.18 mmol), 2-methoxypyridin-4-amine (29.8 mg, 0.240 mmol), followed by a 50% ethyl acetate solution of T3P (972 mg, 1.53 mmol). The reaction was heated to 60 C for 2 hours, after which additional triethylamine (0.304 mL, 2.18 mmol) and T3P solution (972 mg, 1.53 mmol) were added. The reaction mixture was stirred at 60 C for 12 hours, after which it was diluted in water, extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography (Luknova 40g, 20 mL/min) using 10 to 60% ethyl acetate in hexanes over 60 minutes. 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2- methoxypyridin-4-yl)-2-oxoacetamide (31 mg, 0.071 mmol, 33% yield) was isolated as a light-tan solid. NMR (400 MHz, CDC13) delta (ppm): 12.5 (br. s, IH), 8.55 (dd, IH), 8.08 (d, IH), 7.55 (dd, IH), 7.23-7.29 (m, 4H), 7.18 (dd, IH), 6.87 (d, 2H), 5.34 (s, 2H), 3.90 (s, 3H), 2.70 (s, 3H).

References: [1]Patent: WO2012/88469,2012,A1 .Location in patent: Page/Page column 100-102.

10
[ 545384-32-5 ]
[ 73177-35-2 ]

References: [1]Patent: WO2012/88469,2012,A1 .
[2]Patent: US6348474,2002,B1 .

11
[ 73177-35-2 ]
[ 79-04-9 ]
2-chloro-1-(2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		Synthesis of 2-Chloro-1-(2-methyl-1H-pyrrolo [3,2-b]pyridin-3-yl)-ethanone (LXII). To a solution of XX (0.5 g, 3.78 mmol) in dichloromethane (10 mL) was added anhydrous aluminum chloride (2.5 g, 0.018 mol). The mixture was allowed to stir at room temperature for 1 h and then a solution of chloroacetyl chloride (2.1 g, 0.018 mol) in dichloromethane (10 mL) was added dropwise to the reaction mixture. The reaction mixture was allowed to stir 20 under a nitrogen atmosphere, at room temperature, overnight. In the morning the reaction mixture was diluted with methanol (50 mL) and then concentrated in vacuo. The reminaing residue was diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The remaining solid material was 25 triturated with n-pentane to afford X (0.5 g, 63%) as a brown solid; 1H NMR (400 MHz, DMSO-d6) delta 12.38 (s, 1H), 8.45 (d, J= 6.0 Hz, 1H), 7.81 (d, J= 9.6 Hz, 1H), 7.20 (d, J= 13 Hz, 1H), 5.28 (s, 2H) 2.71 (s, 3H); MS (ESI, positive mode) m/z 209/211 (MH+, 35/37Cl).

References: [1]Patent: WO2015/73528,2015,A1 .Location in patent: Page/Page column 152.

12
[ 73177-35-2 ]
[ 3058-39-7 ]
4-(2-methylpyrrolo[3,2-b]pyridin-1-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.4 g		Synth es is of 4-(2-Meth yl-pyrrolo[3,2-b]pyridin-1-yl)-benzonitrile (XXI): In a s ealed tube, a mixture of copper (I) iodide (43 mg, 0.226 mmol), compound X X (0.600 g, 4.53 mmol) and potass ium phosphate (1.60 g, 7.70 mmol) in 1 ,4-dioxane (20 mL) w as sparged with nitrogen gas for 0.5 h. Then trans-(+/-)-1 ,2-cyclohexanediamine (26 mg, 0.226 mmol) and 4-iodo- benzonitrile (1.00 g, 4.53 mmol) where then added to the flask at room temperature and the 30 resulting reaction mixture was heated at 110 oC for 38 h. After cooling to room temperature, the reaction mixture was filtered through celite and the filter pad w as washed with ethyl acetate. The filtrate was concentrated to afford the crude product mixture. The crude was purified by column chromatography on silica gel (100-200 mesh) using 30% ethyl acetate in hexane as the eluant to obtain product XXI (0.4 g) as an off-white solid. 1H NMR (400 MHz, 114 of 363 {//-- DRAFT --//4069/3020WO/00228726/v2} 4069.3020 WO CDCl3): delta 8.45 (dd, J= 5.2, 1 Hz, 1H), 7.93 (d, J= 8.6 Hz, 2H), 7.60 (d, J= 8.2 Hz, 1H), 7.52 (d, J= 8.5 Hz, 2H), 7.21 (dd, J= 8.3, 5.2 Hz, 1H), 6.94 (s, 1H), 2.43 (s, 3H), MS (ESI, positive mode) m/z 234 (MH+).

References: [1]Patent: WO2015/73528,2015,A1 .Location in patent: Page/Page column 114-115.

13
[ 39856-58-1 ]
[ 73177-35-2 ]