Sodium bis(trimethylsilyl)amide → HCID 70984732, compound

Participants

Reaction Conditions

Reaction Steps

NaHMDS (0.228 mL, 0.228 mmol) was added to a dimethylformamide (1 mL) solution of tert-butyl (4R,7S,8S)-7-(2,3-difluorophenyl)-4-hydroxy-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-8-ylcarbamate (20.1 mg, 0.051 mmol) and 1-(1-(1H-imidazole-1-carbonyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (23.7 mg, 0.076 mmol) at 0° C. The reaction was stirred at 0° C. for 1 h and rt for 2 h before quenching with water. The reaction was diluted with ethyl acetate and the organic layer was separated, washed with water and brine and then dried (sodium sulfate), filtered and concentrated. Flash chromatography, eluting with methanol in methylene chloride from 0 to 10% gave the desired product (18.2 mg, 56%): LCMS (M+H=641.38); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.64 (1H, s), 8.07 (1H, d, J=5.0 Hz), 7.31-7.56 (1H, m), 6.93-7.12 (4H, m), 6.22 (1H, d, J=7.5 Hz), 5.24-5.34 (1H, m), 4.96-5.07 (1H, m), 4.32-4.71 (3H, m), 3.61-3.77 (1H, m), 2.88-3.15 (2H, m), 2.29 (4H, d, J=10.5 Hz), 1.83-1.97 (4H, m), 1.30 (9H, s).

Provenance & Evidence