Water → tert-Butyl (1S,2R)-2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (4.8 g, 12.93 mmol) and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (4.16 g, 19.40 mmol) and diisopropylethylamine (3.39 mL, 19.40 mmol) in ACN (20 mL) was stirred at 100° C. for 3 days. Water and EtOAc were added and the aqueous phase was extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 (Hexane/EtOAc=1/1) to give the title compound as a brown amorphous solid (3.31 g, 46.6%). 1H NMR (500 MHz, CDCl3) δ ppm 1.35-2.02 (m, 17H), 3.80 (s, 3H), 3.84 (s, 3H), 4.01 (br s, 1H), 4.20 (s, 2H), 4.23 (br s, 1H), 4.66 (s, 2H), 4.91 (br s, 1H), 6.40-6.52 (m, 2H), 7.20-7.28 (m, 1H). [M+H] calc'd for C27H34ClFN4O5, 549. found, 549.

Provenance & Evidence