Dicyclohexylcarbodiimide → HCID 59556614, compound

Participants

Reaction Conditions

Reaction Steps

(Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.5 g, 2.187 mmol), 4-amino-2-chlorobenzoic acid (0.413 g, 2.405 mmol), DCC (0.496 g, 2.405 mmol), HOBT (0.368 g, 2.405 mmol) were placed in an 80 ml microwave vial and Acetonitrile (12.01 ml) was added. The reaction mixture was stirred for 5 minutes at room temperature before the addition of DIEA (0.840 ml, 4.81 mmol). The reaction mixture was heated to 120° C. for 30 min in a microwave. TLC (50% EA/Hept) indicated 4 spots Rf 0.8, 0.6, 0.5 and 0.3. LCMS (2007—9349) indicated by UV 16% (2.61 mins) to (M+H) 364.31. The solvent was removed and the crude material purified by FCC (50% EA/Hept) to afford 3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline (534 mg, 1.466 mmol, 67.1% yield). LCMS (Table A, Method b) indicated a 99% by UV (3.10 mins) and 92% by ELSD (3.06 mins) to (M+H)+ 364.12.

Provenance & Evidence