Phenyl isocyanate → HCID 19063689, compound

Participants

Reaction Steps

A mixture of 2-(4-Amino-5-oxo-4,5-dihydro-1,2,3a,6-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide (140 mg, 0.361 mmol), prepared as in Intermediate 36, and phenyl isocyanate (39.2 uL, 0.361 mmol) in 5 mL dry DCM is stirred at ambient temperature under nitrogen overnight. After concentrating in vacuo, the residue is chromatographed on flash grade silica gel using 95% ethyl acetate in n-hexane. The fractions containing the product are combined, concentrated in vacuo, and triturated with hexane. After removing the solvent in vacuo, the product is dried overnight at ambient temperature under high vacuum to provide the title compound (84 mg, 0.165 mmol) as a white solid. The product is lyophilized from acetonitrile/water. 1H NMR (300 MHz, d6-DMSO): 0.89-0.96 (m, 6H); 4.02 (d, J=16.3 Hz, 1H); 4.16 (d, J=16.3 Hz, 1H); 4.62-6.73 (m, 1H); 5.99-6.05 (m, 1 H); 6.93 (t, J=7.2 Hz; 1H); 7.10-7.89 (m, 14H); 8.10 (s, 1H); 9.30 (s, 1H). MS (FAB): [M+H]+ 510.

Provenance & Evidence