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With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid In 2-methoxy-ethanol at 70℃; for 24 h;
To a solution of tert-butyl l H-pyrrolo[3,2-c]pyridine-l-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 °C for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo andthe residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00 percent).
100%
With 10 wt% Pd(OH)2 on carbon; hydrogen In acetic acid at 70℃; for 24 h;
To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70° C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00percent).
With hydrogen In methanol; ethanol at 20℃; for 10 h;
To a solution of (5-benzyl-octahydro-pyrrolo[3,2-c]pyridine-l-carboxylic acid tert- butyl ester (777 mg, 2.46 mmol) in IMS (20 mL) was added palladium hydroxide on carbon(5 percent, 50 mg) and the mixture stirred under a hydrogen atmosphere at RT for 1O h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the title compound as a straw coloured oil (550 mg, 99 percent).[M + H]+ 227.3
With hydrogen;5% palladium hydroxide on activated carbon; In methanol; ethanol; at 20.0℃; for 10.0h;
To a solution of (5-benzyl-octahydro-pyrrolo[3,2-c]pyridine-l-carboxylic acid tert- butyl ester (777 mg, 2.46 mmol) in IMS (20 mL) was added palladium hydroxide on carbon(5 %, 50 mg) and the mixture stirred under a hydrogen atmosphere at RT for 1O h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the title compound as a straw coloured oil (550 mg, 99 %).[M + H]+ 227.3
With triethylamine; In dichloromethane; at 20.0℃; for 4.0h;
1-Methyloctahydro-1H-pyrrolo[3,2-c]pyridine To a solution of <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate</strong> (1.05 g, 4.64 mmol, Shah, S. K et. al, Bioorg. Med. Chem. Lett. 2005, 15, 977-982) in DCM (20 mL) was added TEA (1.29 mL, 9.29 mmol) followed by dropwise addition of benzyl chloroformate (0.795 mL, 5.57 mmol) at ambient temperature. After about 4 h, the mixture was diluted with DCM and then washed with water and brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-75% EtOAc in heptane to give 5-benzyl 1-tert-butyl hexahydro-1H-pyrrolo[3,2-c]pyridine-1,5(6H)-dicarboxylate (1.05 g, 63% yield): LC/MS (Table 1, Method a) Rt=2.59 min; MS m/z: 361 (M+H)+.
With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In 2-methoxy-ethanol; at 70.0℃; under 15001.5 Torr; for 24.0h;
To a solution of tert-butyl l H-pyrrolo[3,2-c]pyridine-l-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo andthe residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00 %).
100%
With 10 wt% Pd(OH)2 on carbon; hydrogen; In acetic acid; at 70.0℃; under 15001.5 Torr; for 24.0h;
To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00%).
To a solution of ieri-butyl octahydro-lH-pyrrolo[3,2-c]pyridine-l- carboxylate (0.63 g) in acetone (15 mL) was added 2C03 (1.54 g) and l -bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00 %).
77%
With potassium carbonate; In [(2)H6]acetone;Reflux;
To a solution of <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate</strong> (0.63 g) in acetone (15 mL) was added K2CO3 (1.54 g) and 1-bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00%).
tert-butyl 5-(3-bromo-2-methylphenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With palladium diacetate; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In 1,4-dioxane; at 90.0℃;Inert atmosphere;
A mixture of <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate</strong> (Combi-Blocks catalog ST-7254: 60 mg, 0.265 mmol), 1,3-dibromo-2-methylbenzene (Combi-Blocks cat OT-1437: 199 mg, 0.795 mmol), palladium(II) acetate (5.95 mg, 0.027 mmol), (R)-(+)-2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (16.51 mg, 0.027 mmol), and cesium carbonate (173 mg, 0.530 mmol) in 1,4-Dioxane (5.0 ml) was flushed with N2. The resulting slurry was stirred at 90 C. overnight. After being cooled to room temperature, the reaction mixture was quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel, eluting with ethyl acetate in hexanes (0-50%) to afford the desired product. LC-MS calculated for C19H28BrN2O2 (M+H)+: m/z=395.1; found 395.1.
tert-butyl 5-(2-(5-chloro-6-(4-(ethoxycarbonyl)piperidin-1-yl)nicotinamido)-4-(4-chlorothiophen-2-yl)thiazol-5-yl)octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate[ No CAS ]
ethyl 1-(3-chloro-5-((4-(4-chlorothiophen-2-yl)-5-(octahydro-1H-pyrrol[3,2-c]pyridin-5(6H)-yl)thiazol-2-yl)carbamoyl)pyridin-2-yl)piperidine-4-carboxylate[ No CAS ]
ethyl 1-(3-chloro-5-((4-(4-chlorothiophen-2-yl)-5-(1-cyclohexyloctahydro-1H-pyrrolo[3,2-c]pyridin-5(6H)-yl)thiazol-2-yl)aminoformamide)pyridin-2-yl)piperidine-4-carboxylate[ No CAS ]
5-bromo-4-(4-chlorothiophen-2-yl)-2-aminothiazole[ No CAS ]
[ 1147422-00-1 ]
tert-butyl 5-(2-amino-4-(4-chlorothiophen-2-yl)thiazol-5-yl)octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
170 mg
With triethylamine; In N,N-dimethyl-formamide; at 90.0℃; for 6.0h;
5-(2-amino-4-(4-chlorothiophen-2-yl)thiazol-5-yl)-octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate</strong> (100mg, 0.4mmol), and 5-bromo-4-(4-chloro-thiophen-2-yl)-thiazole-2-amine (157mg, 0.5mmol) were added to N,N-dimethylformamide (4mL), and then triethylamine (447mg, 4.4mmol) was added. The mixture was warmed to 90C and reacted for 6 h. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic phases were combined and washed successively with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to produce a crude product. The crude product was purified with a silica gel column chromatography to produce the title compound as a yellow solid (170mg). ESI-MS (m/z): 441.2 [M + H]+
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