Morpholine → HCID 23510158, compound

Participants

Reaction Steps

To a stirred slurry of morpholine (0.05 ml, 0.51 mmol) and potassium carbonate (0.09 g, 0.68 mmol) in DMF (1.2 ml) was added 6-Chloro-1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide from Example 19 (0.17 g, 0.34 mmol) at room temperature. The reaction was stirred for 48 hours before being partitioned between ethyl acetate and 1N NaOH. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting crude oil was chromatographed (5% MeOH/dichloromethane) to yield 6-chloro-1-(3-morpholin-4-yl-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide (0.05 g, 27%); [M+H=543].

Provenance & Evidence