1,1'-Carbonyldiimidazole → HCID 9910907, compound

Participants

Reaction Conditions

Reaction Steps

4—(Dimethylaminocarbonyl)benzoic acid (described in: Jurewicz, A. T; U.S. Pat. No. 3,607,918, 1971) (38 mg, 0.20 mmol) and 1,1′-carbonyldiimidazole (34 mg , 0.21 mmol) were dissolved in dry N,N-dimethylformamide (4 mL) and stirred at 75° C. for 1.5 h. The reaction mixture was cooled to room temperature and a solution of (S)-3-amino-8-methyl-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (49 mg, 0.19 mmol) in dry N,N-dimethylformamide (5 mL) was added. The reaction mixture was stirred at 50° C. for 14 h and the solvent was evaporated in vacuo giving 120 mg of a crude product. Purification by preparative TLC using chloroform/methanol/conc. NH3 (95:5:0.5) as the eluent afforded 40 mg (48% yield) of the title compound as a white foam: EIMS (70eV) m/z (relative intensity) 436 (26, M+); [α]21D−9° (c 0.20, chloroform).

Provenance & Evidence