Triethylamine → HCID 58468021, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried 100 ml round-bottom flask was dissolved 1-(piperidin-4-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (52.3 mg, 0.150 mmol) in methylene chloride (5 mL) to give a colorless solution. Triethylamine (0.038 mL, 0.28 mmol) was added under nitrogen and the mixture was cooled to −20° C. Trichloromethyl chloroformate (0.012 mL, 0.100 mmol) was added dropwise. The mixture was gradually warmed up with stirring to 10° C. for 1 h, during which time the solution became slightly yellow. The reaction was concentrated to dryness under vacuum. tert-Butyl (5S,6S,9R)-9-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (48.7 mg, 0.125 mmol) and triethylamine (0.038 mL, 0.275 mmol) dissolved in 1 mL tetrahydrofuran (plus 2 mL rinse) was added via cannula at room temperature. More triethylamine (0.038 mL, 0.275 mmol) was added. The resulting faint yellow suspension was stirred under nitrogen overnight. The reaction was diluted with ethyl acetate and washed with water three times. The ethyl acetate layer was separated, dried (sodium sulfate), filtered and concentrated. Flash chromatography using methanol in methylene chloride from 0 to 10% gave the desired product (12 mg, 13%): MS(ESI)[M+H+]=764.38.

Provenance & Evidence