1,3-Bis(benzyloxycarbonyl)-2-methylisothiourea → 1,1-dimethylethyl 7-[2-({[(phenylmethyl)oxy]carbonyl}amino)-1H-imidazo[4,5-b]pyridin-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-dimethylethyl 7-(5,6-diaminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (example 15, step 2) (0.23 g, 0.65 mmol) in acetic acid (10 mL) was added 1,3-bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea (0.27 g, 0.76 mmol) and the resulting mixture was heated at 50° C. After 4 h the reaction mixture was concentrated then suspended in ethyl acetate (10 mL). Filtration followed by washing the cake with ethyl acetate (2×10 mL) provided 1,1-dimethylethyl 7-[2-({[(phenylmethyl)oxy]carbonyl}amino)-1H-imidazo[4,5-b]pyridin-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.3 g, 91% yield) as a white solid. MS (EI) for C28H29N5O5: 516 (MH+).

Provenance & Evidence