Isobutylene oxide → 2-[3-(4-Chlorophenyl)ureido]-6-(2-hydroxy-2-methylpropyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of compound A4 (200 mg, 0.430 mmol), 2,2-dimethyloxirane (155 mg, 2.15 mmol), and diisopropylethylamine (167 mg, 1.29 mmol) in anhydrous N,N-dimethylformamide (1.5 mL) was stirred at room temperature for 2 h and heated to 50° C. in a sealed tube for another 21 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 2% to 6% methanol/methylene chloride to afford compound U1 as a yellow solid (36 mg, 20%): 1H NMR (300 MHz, DMSO-d6) δ 10.97 (s, 1H), 10.19 (s, 1H), 7.70-6.70 (m, 6H), 4.19 (s, 1H), 3.62 (s, 2H), 2.78 (bs, 4H), 2.38 (s, 2H), 1.12 (s, 6H). MS (M+H) 423.

Provenance & Evidence