1,1-Dichloroethane → HCID 66703671, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (138 mg) was added to a dichloroethane (20 mL) solution of 2-{[(1S,2S)-2-aminocyclohexyl]amino}-N-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-4-(trifluoromethyl)benzamide (200 mg), cyclopentanone (40 mg) and acetic acid (29 mg), followed by stirring at room temperature for 1 day. Acetic acid (260 mg), cyclopentanone (140 mg) and sodium triacetoxyborohydride (140 mg) were added to the reaction liquid, followed by stirring for 1 day. A 1 M sodium hydroxide aqueous solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol, 1:0 to 85:15). By treating the resulting free base with 4 M hydrogen chloride/ethyl acetate, 2-{[(1S,2S)-2-(cyclopentylamino)cyclohexyl]amino}-N-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-4-(trifluoromethyl)benzamide hydrochloride (53 mg) was obtained as a white solid.

Provenance & Evidence