Methylamine → 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzylamine

Participants

Reaction Steps

2-[4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzyl]-1,3-isoindolinedione (885 mg) [see Example 10] was added to a solution of 33% w/w methylamine in ethanol (2.2 ml). The reaction mixture was stirred at room temperature for 5 hours after which time the solvent was removed under reduced pressure. The resulting solid was dissolved in 1N aqueous hydrochloric acid solution and dichloromethane. The aqueous layer was then separated and basified to pH 12 with 0.88 aqueous ammonia solution. The mixture was then extracted with ethyl acetate, the organic layer dried over magnesium sulphate and the solvent removed under reduced pressure to afford 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzylamine (369 mg) as a white solid.

Provenance & Evidence