Hydrochloric Acid → HCID 178455649, compound

Participants

Reaction Steps

Hydrochloride of 1-(3-dimethylaminopropyl)-3-ethylcarbodimide (87 mg) and 1-hydroxybenzotriazole (90 mg) were added to a DMF solution (4.0 mL) containing 4-tert-butylsulfonylaminocyclohexanecarboxylic acid (99 mg) as prepared by the above-described preparation method and 4-trifluoromethyl-1,2-phenylenediamine (66 mg), followed by stirring at room temperature for 16 hrs. The reaction solution was diluted with ethyl acetate, and the organic layer was washed with aqueous saturated sodium hydrogencarbonate and sodium chloride solutions, successively, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give a crude amide containing trans-N-(2-amino-5-trifluoromethylphenyl)-4-tertbutylsulfonylaminocyclohexanecarboxamide. The crude amide was admixed with phosphorus oxychloride (1.0 mL), and the mixture was heated under stirring at 100° C. for 2 hrs. The excess phosphorus oxychloride was distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The organic layer was washed with aqueous saturated sodium hydrogencarbonate and sodium chloride solutions successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was crystallized from isopropyl ether to give the title compound (48.2 mg).

Provenance & Evidence