Dimethylformamide → (S)-tert-Butyl (2-(benzyloxy)-5-(((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)pyridin-3-yl)carbamate

Participants

Reaction Steps

To a stirred solution of 5-(benzyloxy)-6-((tert-butoxycarbonyl)amino)nicotinic acid (800 mg, 0.0023 mol) in DMF (10 mL), were added (S)-(3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methanamine hydrochloride (790 mg, 0.0023 mol, Intermediate 6), HATU (1.325 g, 0.0034 mol) and DIPEA (900 mg, 0.0069 mol). The reaction mixture was then stirred for 12 h at rt. Reaction progress was monitored by TLC (100% EtOAc). After completion of the reaction, water (8 mL) was added, and the aqueous solution was extracted with EtOAc (5 mL×3) and concentrated to provide the product. The product thus obtained was purified by column chromatography, silica gel (100-200 mesh), using 80-100% EtOAc in petroleum ether as the eluent to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 9.52 (d, J=7.6 Hz, 1H), 9.10 (s, 1H), 8.47 (t, 7.5 Hz, 2H), 7.93 (d, J=1.8 Hz, 1H), 7.82 (dd, 0.9, 9.6 Hz, 1H), 7.63-7.46 (m, 4H), 7.40-7.33 (m, 4H), 6.75 (d, J=7.8 Hz, 1H), 5.20 (s, 2H), 1.40 (s, 9H).

Provenance & Evidence