HCID 178418361, compound → HCID 178454000, compound

Participants

Reaction Steps

Palladium on carbon 10% by weight Degussa type (50 mg) was added to a solution of phenylmethyl 4-cyano-3-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}benzoate (71.8 mg, 0.16 mmol) in ethyl acetate (3 mL) and methanol (400 uL). The mixture was subjected to 1 atm of hydrogen for 70 min. The catalyst was then removed by filtration through celite. The resulting filtrate was concentrated to provide 4-cyano-3-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}benzoic acid (55.8 mg, 0.16 mmol) which was carried into the subsequent step without further purification. 1H NMR (400 MHz, CD3OD): 7.47 (d, 1H), 7.37 (s, 1H), 7.24 (d, 1H), 3.47-3.21 (m, 2H), 2.09 (m, 2H), 1.98 (m, 2H), 1.88 (m, 2H), 1.43 (s, 9H), 1.24 (m, 2H); MS (EI) for C19H25N3O4: 304 (MH+-tert-butyl).

Provenance & Evidence