1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59846223, compound

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Reaction Steps

A mixture of 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid (0.2 g, 0.53 mmol), 4-amino-cyclohexanol (61 mg, 0.53 mmol), EDCI (152 mg, 0.8 mmol), HOBt (25 mg), DIPEA (1 mL) in THF (50 mL) was stirred at RT overnight. The resulting mixture was evaporated under reduced pressure, and the residue partitioned between water and EtOAc. The resulting precipitate was collected by filtration and dried in a vacuum oven, the filtrate separated, the organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (EtOAc/hexane, 75:25) and combined with the solid collected to yield 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-N-(4-hydroxy-cyclohexyl)-benzamide (197 mg). MS=475 [M+H]+.

Provenance & Evidence