Phenyl isocyanate → HCID 19063681, compound

Participants

Reaction Steps

According to Process A, phenyl isocyanate (0.065 mL, 0.602 mmol) is added to a solution of 2-(3-Amino-5-methyl-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (219 mg, 0.602 mmol), prepared as in Intermediate 24, under nitrogen in DCM (3 mL). The reaction mixture is stirred at ambient temperature overnight and then concentrated in vacuo. The residue is dissolved in ethyl acetate, washed twice with 1N HCl, dried over anhydrous magnesium sulfate, and then concentrated again to a residue. The crude product is purified by reversed-phase HPLC on a C-18 column with 60% acetonitrile in aqueous trifluoroacetic acid (0.1% v/v) over 30 min. at 100 mL/min. Fractions containing the product are combined, frozen and lyophilized to provide the title compound as a white lyophile (92 mg, 0.190 mmol). 1H NMR (300 MHz, CDCl3) δ=1.02-1.25 (m, 6H); 2.59 (s, 3H); 4.08 (d, J=16.9 Hz, 1H); 4.17 (d, J=16.9 Hz, 1H); 4.93-5.00 (m, 1H); 5.56 (d, J=6.3 Hz, 1H); 7.02-7.61 (m, 14H); MS(FAB): [M+H]+ =484.

Provenance & Evidence