N-methyl-2-pyrrolidone → HCID 178496462, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL sealable tube loaded with 1-(2-methanesulfonyl-pyrimidin-4-yl)-1H-benzotriazole (99.1 mg, 0.36 mmol) were added NMP (1 mL) and diisopropylethylamine (0.19 mL, 1.09 mmol). To a second 5 mL sealable tube loaded with N-(4-amino-cyclohexyl)-2-methoxy-acetamide (100 mg, 0.36 mmol) was added NMP (1 mL). Both tubes were heated at 120° C. and at complete dissolution of the solids the solution of 1-(2-methanesulfonyl-pyrimidin-4-yl)-1H-benzotriazole was transferred via cannula into the tube containing the solution of N-(4-amino-cyclohexyl)-2-methoxy-acetamide. The resulting mixture was stirred for 1.5 hours at 120° C., then cooled to RT and poured into water (15 mL). The resulting mixture was stirred overnight, then diluted with DCM and washed with water. The aqueous layer was separated and extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give an oil which was dissolved in a small amount of EtOAc and hexane was added to precipitate the solids. The resulting mixture was allowed to settle for 1 h, after which the liquid supernatant was carefully decanted away. The remaining solid was dried under reduced pressure to yield 86 mg (63% yield) of trans-N-[4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-2-methoxy-acetamide. MS=381 [M+H]+; MP=233.5-235.4° C.

Provenance & Evidence