4-(4-Isothiocyanato-3-methylphenyl)morpholine → N-(7-Fluoro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[2-methyl-4-(4-morpholinyl)phenyl]thiourea

Participants

Reaction Conditions

Reaction Steps

As illustrated in the scheme above, a solution of 3-amino-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (0.0056 g, 0.020 mmol) and 4-(4-isothiocyanato-3-methylphenyl)morpholine (0.0048 g, 0.020 mmol) in DMA (0.5 mL) was heated at 70° C. for 16 h. The reaction was cooled and concentrated in vacuo, and the residue was lyophilized to provide the title compound (0.0104 g, quantitative). 1H-NMR (CDCl3): δ 7.63-7.58 (m, 2H), 7.50-7.45 (m, 1H), 7.44-7.36 (m, 4H), 7.36-7.26 (m, 3H), 7.09 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 6.85-6.78 (m, 2H), 6.09-6.05 (m, 1H), 3.90-3.83 (br m, 4H), 3.41 (s, 3H), 3.21-3.15 (br s, 4H), 2.36 (s, 3H). MS (ESI) (M+H)+=518.HRMS calculated for (C28H28FN5O2S+H) (M+H)+: 518.2026. Found (ESI): 518.2117.

Provenance & Evidence