P-Toluic Acid → HCID 54306168, compound

Participants

Reaction Conditions

Reaction Steps

4-Methylbenzoic acid (22 mg, 0.16 mmol) and 1,1′-carbonyldiimidazole (27 mg, 0.17 mmol) were dissolved in dry N,N-dimethylformamide (2 mL) and stirred at 75° C. for 1 h. The reaction mixture was cooled to room temperature and a solution of (S)-3-amino-8-methyl-5-(methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (40 mg, 0.15 mmol) dissolved in dry N,N-dimethylformamide (4 mL) was added. The reaction mixture was stirred at room temperature for 4 days and the solvent was evaporated in vactio. The crude material was partitioned between methylene chloride (40 mL) and water (10 mL). The organic phase was washed with water (10 mL) and brine (5 mL) and dried (MgSO4). The solvent was evaporated in vacuo giving 48 mg of a crude product. Purification by preparative TLC on silica using chloroform/ethanol (saturated with ammonia) (15:1) as the eluent afforded 23 mg (40% yield) of the title compound as a white solid: mp 191-192° C.; EIMS (70 eV) m/z (relative intensity) 379 (100, M+); [α]21D−7° (c 0.10, chloroform).

Provenance & Evidence