Trifluoroacetic acid → 1-[4-[2-(Azetidin-1-yl)-ethoxy]-4-pyridin-3-yl-piperidin-1-yl]-2-[[(2S)-1-[(4-methoxy-2,6-dimethyl-phenyl)sulfonyl]-piperidin-2-yl]-methoxy]-ethanone

Participants

Reaction Conditions

Reaction Steps

After the BOC deprotection of tert-butyl 4-(2-(azetidin-1-yl)ethoxy)-4-(pyridin-3-yl)piperidine-1-carboxylate [amine E] (0.15 g, 1.2 eq.) in the presence of TFA (10-13 eq.) in methylene chloride (see e.g. stage (iii)/amine H), the amine was added to a cooled (0° C.) solution comprising (S)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid [acid D] (1 eq.), EDCl (1.5 eq.), HOBT (1 eq.) and DIPEA (3 eq.) in methylene chloride (10 ml). When the addition was complete, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with methylene chloride and washed with aqueous ammonium chloride solution and aqueous sodium bicarbonate solution. After concentration, the crude product was purified by means of column chromatography (Alox). Yield: 39%. MS, Rt=2.7 min, m/z=615.4 [MH]+

Provenance & Evidence