Dicyclohexylcarbodiimide → HCID 75989777, compound

Participants

Reaction Steps

To a stirred solution of 4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (200 mg, 0.63 mmol) in dimethylformamide (1.5 mL) were added chromane-2-carboxylic acid (124 mg, 0.70 mmol) and 1H-benzotriazol-1-ol (94 mg, 0.70 mmol). The reaction mixture was poured at room temperature on a cartridge filled with 1.44 g of silica linked with N,N′-dicyclohexylcarbodiimide (loading: 1.05 mmol/g). After one night at room temperature, the cartridge was eluted with 1 mL of dimethylformamide. The filtrated solution was then poured on a cartridge filled with 1.5 g of basic alumina. After 2 hours of reaction a room temperature, the cartridge was rinsed twice with 10 mL of ethyl acetate. The combined filtrated solutions were evaporated in vacuo to yield a yellow oil. Purification on silica gel afforded of N-{4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}chromane-2-carboxamide as a colorless oil [150 mg, yield 44%; HPLC/MS: nm/z=476 (M+H); log P(HCOOH)=3.78].

Provenance & Evidence