tert-Butyl bromoacetate → tert-butyl 2-{3-carbamoyl-2-[3-(4-chlorophenyl)ureido]-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl}acetate

Participants

Reaction Steps

A solution of compound A4 (300 mg, 0.646 mmol), diisopropylethylamine (0.350 mL, 1.97 mmol), and tert-butyl 2-bromoacetate (0.140 mL, 0.950 mmol) in tetrahydrofuran (4 mL) was stirred at room temperature for 8 h. After this time, the reaction mixture was diluted with methylene chloride (10 mL), sonicated, and filtered to afford compound E1 as a light yellow solid (191 mg, 64%): 1H NMR (500 MHz, DMSO-d6) δ 10.93 (s, 1H), 10.18 (s, 1H), 7.59-7.29 (m, 5H), 6.89 (bs, 1H), 3.61 (s, 2H), 3.30 (s, 2H), 2.82-2.76 (m, 4H), 1.43 (s, 9H). MS (M+H) 465.

Provenance & Evidence