Dimethylformamide → HCID 131733231, compound

Participants

Reaction Steps

Following a procedure similar to the one in Example 36, 1-(4-chlorophenyl)-4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (100 mg, 0.251 mmol), 4-bromobenzamide (60 mg, 0.301 mmol), cesium carbonate (245 mg, 0.752 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (20 mg, 0.0251 mmol) in DMF (2.0 mL) and water (0.5 mL) gave the desired product (10.0 mg, 10%) as a colorless oil. To a solution of the benzodiazepine (10.0 mg, 0.025 mmol) in methanol (1 mL) and water (3 mL) was added L-tartaric acid (4.0 mg, 0.025 mmol) and the resultant solution was lyophilized overnight to give 4-(1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-yl)benzamide, L-tartrate salt (13.6 mg, 97%, AUC HPLC>99%) as a yellow solid: 1H NMR (CD3OD, 500 MHz) δ 7.97 (d, J=8.4 Hz, 2H), 7.87 (s, 1H), 7.78-7.75 (m, 3H), 7.28 (d, J=8.3 Hz, 1H), 7.22 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 4.43 (s, 1.3H), 4.27 (s, 2H), 3.98 (bs, 2H), 3.35-3.33 (m, 2H), 2.86 (s, 3H); ESI MS m/z 392 [M+H]+.

Provenance & Evidence