Citric Acid → HCID 178458429, compound

Participants

Reaction Steps

To iodoacetic acid (242 mg, 1.3 mmol) in N,N-dimethylformamide (2 mL) at −20 C is added N-methylmorpholine (142 uL, 1.3 mmol) and isobutylchloroformate (178 uL, 1.3 mmol). After 5 min (4Z)-4-{[(3-hydroxy-4-propoxybenzyl)amino]methylene}-6-iodoisoquinoline-1,3(2H,4H)-dione (250 mg, 0.52 mmol) is added. The reaction mixture is allowed to warm to 25 C. After 24 h 15% aq. Citric acid is added. The resulting precipitate is filtered and washed with water to give a brown solid (352 mg). A portion of this material (50 mg) is chromatographed on silica gel (CH2Cl2/MeOH) to give the title compound as a tan powder (23 mg). MS (ESI) m/z 555 (M+H)+1.

Provenance & Evidence