3-Amino-7-chloro-1,3-dihydro-5-(6-methoxy-2-pyridinyl)-1-methyl-2H-1,4-benzodiazepin-2-one → N-[7-Chloro-2,3-dihydro-5-(6-methoxy-2-pyridinyl)-1-methyl-2-oxo-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-chloro-1,3-dihydro-5-(6-methoxy-2-pyridinyl)-1-methyl-2H-1,4-benzodiazepin-2-one (0.0113 g, 0.0342 mmol) and 4-(4-isothiocyanato-3-methylphenyl)morpholine (0.0080 g, 0.034 mmol) in (CH2Cl)2 (0.9 mL) was heated at 70° C. for 20 h. The reaction was cooled and concentrated in vacuo, and the residue was purified by silica gel column chromatography (2:1 CH2Cl2:EtOAc) to provide the title compound (0.0172 g, 89%) as a slightly yellow solid. 1H-NMR (CDCl3): δ 7.79 (dd, J=0.8 Hz, J=7.2 Hz, 1H), 7.70-7.65 (m, 2H), 7.54 (dd, J=2.4 Hz, J=8.8 Hz, 1H), 7.42 (br s, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.28-7.25 (m partially hidden under CHCl3, 2H), 6.85-6.80 (m, 3H), 6.14 (m, 1H), 3.88-3.85 (m, 4H), 3.78 (s, 3H), 3.40 (s, 3H), 3.22-3.18 (m, 4H), 2.36 (s, 3H). MS (M+H+=565.

Provenance & Evidence