1,1'-Carbonyldiimidazole → HCID 178447221, compound

Participants

Reaction Steps

According to Process B, a mixture of of 1,1'-carbonyldiimidazole (28.6 mg, 0.176 mmol) and 2-(3-Amino-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (75.0 mg, 0.176 mmol), prepared as in Intermediate 13, in anhydrous THF (5 mL) is stirred at ambient temperature under a nitrogen atmosphere for approximately 30 min. and then heated to reflux. After refluxing for 2 hrs, 3-(2H-tetrazol-5-yl)-phenylamine hydrochloride (36.5 mg, 0.185 mmol), prepared as in Intermediate 17, is added in one portion and the reaction is held at reflux for an additional 5 hrs and then concentrated in vacuo to a residue. The residue is purified by reversed-phase HPLC on a C-18 column with a gradient elution of 30-68% 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 (37 mg, 0.060 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.04 (d, 6H); 4.21 (d, J=16.4 Hz, 1H); 4.31 (d, J=17.1 Hz, 1H); 4.79-6.86 (m, 1H); 5.35-5.36 (m, 1H); 7.32-7.78 (m, 19H); 8.26 (b, 1H); 9.38 (b, 1H); MS (ESI): [M+H]+ =614.

Provenance & Evidence