Triethylamine → HCID 44251363, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one [Burgey et al. U.S. Pat. No. 6,953,790 B2] (16 mg, 0.050 mmol) in THF (8 mL) at 0° C. was added 4-nitrophenyl chloroformate (11 mg, 0.055 mmol) and triethylamine (0.015 mL, 0.11 mmol) and the resulting mixture was stirred at 0° C. for 1 h. A solution of 3-methyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one trifluoroacetate from Step C (34 mg, 0.074 mmol) and triethylamine (0.042 mL, 0.30 mmol) in CHCl3 (8 mL) was added and the resulting mixture was stirred at ambient temperature for 18 h then concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (20 mL) and saturated aqueous NaHCO3 (10 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=581 (M+1). HRMS: m/z=581.2265; calculated m/z=581.2294 for C27H30F5N6O3.

Provenance & Evidence