1,2-Dichloroethane → HCID 178485437, compound

Participants

Reaction Steps

3-(3,4-Diamino-phenoxy)-N-methyl-benzamide (Step C, 400 mg, 1.5 mmol, 1.0 eq.) was dissolved in anh. CH3CN (10 mL) and a solution of 1-(2-chloro-5-isothiocyanato-benzyl)-4-methyl-piperazine (330 mg, 1.2 mmol, 0.8 eq.) in CH3CN (10 mL) was added dropwise. The reaction was stirred at RT for 2 h. EDC (240 mg, 1.3 mmol, 0.9 eq.) was added, the mixture was heated to 80° C. and stirred for 2 h. The CH3CN was evaporated and the crude compound was dissolved in CH2Cl2, washed with water and sat. NaHCO3 (aq.). The organic layer was dried (MgSO4), filtered and concentrated. Further purification by column chromatography (0-10% EtOH/CH2Cl2, two runs were required) gave pure 3-{2-[4-chloro-3-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-1H-benzimidazol-5-yloxy}-N-methyl-benzamide. MS m/z=505.2 (M+H)+; MW Calc'd for C27H29N6O2: 504.20.

Provenance & Evidence