Methanol → HCID 86731025, compound

Participants

Reaction Steps

To a mixture of 1,1′-carbonyldiimidazole (13 mg) and methylene chloride (1 mL) was added 4-dimethylaminopyridine (8 mg), followed by 1-{[(4aR*,6R*,8aR*)-2-amino-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[2-(dimethylamino)ethyl]-1-propylurea (example 1-15) (30 mg) while stirring under ice bath cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added 1,1′-carbonyldiimidazole (13 mg), followed by 4-dimethylaminopyridine (8 mg) and warmed to room temperature and stirred for 1 hour. To the reaction mixture was added 1,1′-carbonyldiimidazole (50 mg), followed by 4-dimethylaminopyridine (32 mg) while stirring at room temperature and stirred at the same temperature for 12 hours. To the reaction mixture was added methanol (0.003 mL) while stirring at room temperature and stirred at the same temperature for 1 hour. The mixture was purified by aminopropyl silica gel column chromatography (eluent: 0%-10% methanol/methylene chloride, gradient elution) to give the title compound (18 mg). The structure was illustrated in Table 11.

Provenance & Evidence