Chloroform → HCID 58608146, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of acid 4k (2.42 g, 5.75 mmol, 1.0 equiv) in CHCl3 (30 mL) was added oxalyl chloride (2.5 mL, 28.7 mmol, 5.0 equiv) followed by DMF (ca. 40 μL). The mixture was heated to 65° C. After 3 hr, the solvent was removed in vacuo and the resulting residue was taken up in CH2Cl2 (20 mL). 1-Methylpiperazine (1.3 mL, 11.5 mmol, 2.0 equiv) was added followed by Et3N (0.80 mL, 5.75 mmol, 1.0 equiv) and the solution was stirred at ambient temperature for 3 h. The solution was diluted with CH2Cl2 (20 mL) and washed with H2O and brine. After drying with MgSO4 and concentration in vacuo, the residue was purified by silica gel chromatography (5% MeOH:CH2Cl2) to provide chloride 61. MS (MH+) 432; Calculated 431.1 for C25H22ClN3O2.

Provenance & Evidence