Citric Acid → HCID 44621738, compound

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Reaction Steps

A solution of [2-[(3-methyl-butyl)-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-acetic acid methyl ester (prepared using 3-methyl-iodo-butane in place of 3-bromo-2-methylprepene as described in Example 41) 55 mg, 0.1 mmol) in NaOH (1N, 0.5 mL) and THF (3 mL) was stirred at 40° C. overnight. The mixture was cooled to room temperature, acidified with 10% citric acid, extracted with CH2Cl2 (3×). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (5-20% ethyl acetate in CH2Cl2) to give the product as a white solid (50 mg, 59%). 1H NMR (300 MHz, CDCl3) δ 8.13 (d, J=8.29 Hz, 2H), 7.68 (dd, J=8.48, 13.37 Hz, 4H), 7.38 (d, J=8.29 Hz, 2H), 7.14 (s, 1H), 6.47 (s, 1H), 4.12 (d, J=15.45 Hz, 2H), 3.55 (s, 2H), 1.58-1.68 (m, 3H), 0.96 (d, J=6.40 Hz, 6H). MS m/e 511.2 (M+H).

Provenance & Evidence