Ammonium Hydroxide → HCID 178458677, compound

Participants

Reaction Steps

To a solution of trans-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexanecarboxylic acid (0.53 g, 1.263 mmol) in DMF (5 mL) was added CDI (0.410 g, 2.53 mmol). The reaction was stirred at RT for 1 hour, and then concentrated aqueous ammonium hydroxide (0.098 mL, 2.53 mmol) was added, and the reaction was stirred overnight. After 16 hours, the reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography, eluting with 50-100% (90:9:1 DCM/MeOH/NH4OH)/DCM, to provide trans-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexanecarboxamide as an orange powder (0.39 g, 73.8% yield). MS, m/z (C22H34FN4O4): calcd, 418.3. found, 419.1 [M+H].

Provenance & Evidence