Triethylamine → N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-urea

Participants

Reaction Conditions

Reaction Steps

As illustrated in the scheme above, a mixture of 4-(dimethylamino)-1-naphthalenecarboxylic acid (0.1 mmol), diphenylphosphoryl azide (0.15 mmol) and triethylamine (0.3 mmol) in toluene (10 ml) was heated at reflux overnight. The solvent was evaporated in vacuo, and then the residue was redissolved in dichloroethane, added to INTERMEDIATE 1 (0.08 mmol) and heated at 70° C. for 4 hours. The solvent was evaporated in vacuo and the residue was taken in dichloromethane (50 ml). The organic phase was washed with brine (2×10 ml); the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether and the title compound was obtained as a colorless solid (9 mg, 22%); 1H-NMR (CDCl3): δ 8.27 (m, 1H), 8.11 (m, 1H), 7.60 (d, J=8 Hz, 1H), 7.77-7.29 (m, 10H), 7.08 (d, J=8.4 Hz, 1H), 6.75 (br s, 2H), 5.56 (d, J=8.4 Hz, 1H), 3.39 (s, 3H) and 2.90 (s, 6H); MS (ESI) (M+H)+=512.

Provenance & Evidence