Phenyl isocyanate → 2,3,4,5-Tetrahydro-N-(4-methoxyphenyl)-N-(1-methylethyl)-2,4-dioxo-3-[[(phenylamino)carbonyl]amino]-5-(2-pyridinyl)-1H-1,5-benzodiazepine-1-acetamide

Participants

Reaction Steps

A solution of phenyl isocyanate (25.6 mg) in methylene chloride (1 ml) was added to a solution of 2-(3-Amino-2,4-dioxo-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (100 mg) in methylene chloride (1 ml) and the resultant mixture was stirred at rt for 4 h. The solvents were removed in vacuo and the residue was recrystalised from ethyl acetate to afford the title product (44 mg) as an off-white solid. 1H NMR (300 MHz, CDCl3); 1.03 (2×d, J=7 Hz, 6H), 3.81 (s, 3H), 4.17 (d J=16 Hz, 1H), 4.37 (d, J=16 Hz, 1H), 5.0 (sept, J=7.1 Hz, 1H), 5.40 (d, J=6.3 Hz, 1H), 6.40 (d, J=5.3 Hz, 1H), 6.8-7.3 (m, 17H), 7.80 (br, 1H), 8.42 (d, J=3.9 Hz, 1H).Tlc (10% MeOH, CH2Cl2) Rf=0.53. m/z [MH]+ =593.

Provenance & Evidence