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[ CAS No. 73177-35-2 ] {[proInfo.proName]}

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Chemical Structure| 73177-35-2
Chemical Structure| 73177-35-2
Structure of 73177-35-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 73177-35-2 ]

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Product Details of [ 73177-35-2 ]

CAS No. :73177-35-2 MDL No. :MFCD12923706
Formula : C8H8N2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :FTDBLXOLABKXNQ-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :11586310
Synonyms :

Calculated chemistry of [ 73177-35-2 ]      Expand+

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 : 28.68 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 1.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.25
Solubility : 0.741 mg/ml ; 0.0056 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 2.77 mg/ml ; 0.0209 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0721 mg/ml ; 0.000546 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 73177-35-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

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   1~14

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  • [ 4916-40-9 ]
  • 3
  • <i>N</i>-<2-methyl-<3>pyridyl-diacetamide [ No CAS ]
  • [ 73177-35-2 ]
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  • [ 73177-35-2 ]
  • [ 89-75-8 ]
  • [ 219762-87-5 ]
YieldReaction ConditionsOperation 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)
  • 5
  • [ 1383924-63-7 ]
  • [ 73177-35-2 ]
YieldReaction ConditionsOperation 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.
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  • [ 104-83-6 ]
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YieldReaction ConditionsOperation 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).
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  • 2-chloro-1-(2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 12
  • [ 73177-35-2 ]
  • [ 3058-39-7 ]
  • 4-(2-methylpyrrolo[3,2-b]pyridin-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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+).
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  • [ 39856-58-1 ]
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  • 2-prop-1-ynyl-pyridin-3-ylamine [ No CAS ]
  • [ 73177-35-2 ]
YieldReaction ConditionsOperation in experiment
0.15 g With potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 4h; Syn th es is of 2-Meth yl-1H-pyrrolo[3,2-b]pyrid ine (X X): To a cold solution of compound XIX (200 mg, 1.50 mmol) in anhydrous N,N-dimethylformamide (5 mL) w as added s olid potass ium tert-butoxide (170 mg, 3.02 mmol) in a portion-wise manner. The resulting mixture was allowed to s tir at room temperature for 4 h. The reaction mixture was poured into cold water (10 mL) and then extracted with diethyl ether (2 x 10 mL). The organic layer 20 was dried over anhydrous sodium sulfate and then concentrated under vacuum to afford product X X (0.150 g) as an off-white solid. 1H NM R (400 M Hz, D MSO-d6): delta 11.13 (s, 1 H ), 8.19 (dd, J= 4.8, 1 Hz, 1 H ), 7.59 (d, J= 8.1 H z, 1 H), 6.97 (dd, J= 8, 4.6 Hz, 1 H), 6.24 (s, 1 H), 2.42 (s, 3H); MS (ESI, positive mode) m /z 133 (M H+).
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