Acrylamide → 6-(3-Amino-3-oxopropyl)-2-[3-(4-chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

Participants

Reaction Steps

A solution of compound A4 (200 mg, 0.431 mmol), acrylamide (156 mg, 2.19 mmol), and diisopropylethylamine (0.400 mL, 2.25 mmol) in N,N-dimethylformamide (2.5 mL) was heated at 50° C. for 8 h. After this time, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with 0% to 10% methanol/methylene chloride to afford compound D1 as a yellow solid (180 mg, 99%): 1H NMR (300 MHz, DMSO-d6) δ 10.95 (s, 1H), 10.19 (s, 1H), 7.59-7.29 (m, 6H), 6.90-6.73 (m, 2H), 3.48 (s, 2H), 2.83-2.65 (m, 6H), 2.33-2.25 (m, 2H). MS (M+H) 422.

Provenance & Evidence