Aniline → HCID 67696640, compound

Participants

Reaction Conditions

Reaction Steps

0.59 mL (6.7 mmol) of oxalyl chloride in 25 mL of CH2Cl2 is added dropwise to a solution of 1.8 g (3.4 mmol) of [1-(Isopropyl-(4-methoxy-phenyl)-carbamoylmethyl)-3-methyl-2,4-dioxo-5-(4-chloro-phenyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-acetic acid, prepared as in Intermediate 3, and 0.013 mL of DMF in 50 ml of CH2Cl2 cooled to 0° C. The solution is stirred at RT for 2.5 h and subsequently concentrated in vacuo to a dark grey foam. The crude acid chloride is dissolved in 60 mL of CH2Cl2, cooled to 0° C. and a solution of 0.92 mL (10.1 mmol) of aniline in 15 mL of CH2Cl2 is added dropwise. The mixture is stirred at RT for 2 h. After diluting with 200 mL of 1N HCl, the mixture is extracted with EtOAc (×2). The organic extract is washed with 1N HCl and brine, dried over MgSO4 and concentrated in vacuo to a grey foam. Purification by silica gel flash chromatography (50% EtOAc/petroleum ether) followed by recrystallization from EtOAc/petroleum ether gave 1.14 g of the title compound as a white powder: m.p. 170°-6° C.; 1H NMR (CDCl3 300 MHz) δ7.88 (s, 1H), 7.6-6.8 (m, 17H), 5.01 (m, 1H), 4.65 (d, 1H, J=17), 3.84 (s, 3H), 3.82 (d, 1H, J=17), 2.45 (q, 2H, J=15), 1.67 (s, 3H), 1.11 (m, 6H); low resolution MS (FAB) m/e 639 (MH+).

Provenance & Evidence