Trifluoroacetic acid → (3-(Methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 2,2,2-trifluoroacetate

Participants

Reaction Steps

The title compound was prepared according to general procedure D described in connection with Scheme 2. tert-Butyl 3-(methoxymethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidine-1-carboxylate (1.7 g, 3.84 mmole) was dissolved in 50 mL CH2Cl2 and 16 mL TFA was added at RT. The reaction mixture was stirred for 17 h and the solvents evaporated. The residue was dissolved in CH2Cl2 and the organic layer was washed twice with 50 mL of saturated NaHCO3 and then dried over Na2SO4. The solvent was evaporated to give product (1.3 g, quantitative yield) of the desired product. 1H NMR (400 MHz, CDCl3): δ 8.71 (s, 1H), 7.70 (s, 1H), 4.81 (s, 2H), 4.13-3.89 (m, 2H), 3.52-3.43 (m, 3H), 3.29 (s, 3H), 3.12-2.97 (m, 5H), 2.22-2.18 (m, 1H), 2.04-1.97 (m, 1H); MS (ESI) m/z: Calculated for C16H20F3N3O2(free base): 343.2. found: 344 (M+H)+.

Provenance & Evidence