Tetrahydrofuran → HCID 178457890, compound

Participants

Reaction Steps

To a vigorously stirring solution of 2-(3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (0.070 g) in tetrahydrofuran (3 ml) at ambient temperature was added 1,1-carbonyldiimidazole (0.025 g) in one portion. The resulting was stirred for 90 minutes at ambient temperature. 3-(2H-tetrazol-5-yl)-phenylamine hydrochloride (31.3 mg), was added in one portion and the reaction mixture was heated to reflux overnight. The reaction mixture was filtered and the filtrate concentrated to a yellow oil. The oil was purified by preparative RP-HPLC on a C-18 column with a gradient elution of 43-53% acetonitrile in water with 0.1% trifluoroacetic acid buffer over a 30 minute period at a rate of 100 ml/min. Fractions containing the desired material were combined, frozen and lyophilized to provide the title compound as a white powder (50 mg). 1H NMR (300 MHz, DMSO-d6): d 0.96(d, J=7.3 Hz, 3H), 0.98(d, J=7.3 Hz, 3H), 4.20(d, J=16.8 Hz, 1H), 4.49(d, J=17.1 Hz, 1H), 4.79(m, 1H), 5.06(d, J=7.3 Hz, 1H), 6.98(m, 2H), 7.24-7.55(m, 17H), 8.17(s, 1H), 9.44(s, 1H) MS (FAB): m/z=630.2 (MH+) (calcd. for C34H31N9O4 =629.2502) TLC (CH2Cl2 /CH3OH(9:1)): Rf =0.24 RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 43-53% CH3CN in H2O with 0.1% TFA buffer; 30 minutes; 1 ml/min): tf =15 min (to =3min).

Provenance & Evidence