Acetic Acid → 1-{1-[(3S)-4-[[3-Bromo-5-(trifluoromethyl)benzoyl](methyl)amino]-3-(4-fluorophenyl)butyl]azetidin-3-yl}-N,N-dimethylpiperidine-4-carboxamide diformate

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Reaction Steps

A mixture of 3-bromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5-(trifluoromethyl)benzamide (see method 1; 0.178 g, 0.40 mmol), 1-azetidin-3-yl-N,N-dimethylpiperidine-4-carboxamide (see method 3; 0.084 g, 0.40 mmol), acetic acid (0.3 mL), (polystyrylmethyl)trimethylammonium cyanoborohydride (0.098 g, 0.52 mmol) and methanol was stirred at RT for 6 h. The resin was filtered off and washed with methanol. The solvent of the filtrate was removed by evaporation and the product was purified by reversed phase chromatography (C8) using acetonitrile and aqueous ammonium formate/formic acid solution (0.1 M N4CO2H, 0.1 M HCO2H, pH 4) as eluent. There was obtained 0.23 g (77%) of the title compound. 1H NMR (500 MHz, CD3OD): δ 1.6-2.0 (cm, 6H), 2.6-4.2 (cm, 24H), 7.0-8.0 (cm, 6H), 8.4 (s, 1H); LCMS: m/z 642 (M+1)+.

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