Trifluoroacetic acid → (E)-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-1H-spiro[[1,8]naph-thyridine-3,4'-piperidin]-2(4H)-one 2,2,2-trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (E)-tert-butyl 2-oxo-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-1′-carboxylate (Compound 1) (0.6 g, 1.52 mmol) in CH2Cl2 (15 mL) was added trifluoro acetic acid (0.58 mL, 7.61 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 4 h. Then the reaction mixture was rotary evaporated under vacuum to get residue which was triturated with diethyl ether to get the desired compound as a yellow solid (500 mg, 82%); 1H NMR (400 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.50-8.32 (m, 3H), 8.07 (s, 1H), 7.71 (d, J=3.4 Hz, 1H), 7.61 (d, J=3.4 Hz, 1H), 7.46 (d, J=15.7 Hz, 1H), 7.28-7.14 (m, 1H), 5.68-5.65 (m, 1H), 4.26-4.20 (m, 1H), 4.08-4.02 (m, 1H), 3.78-3.72 (m, 3H), 3.68-3.62 (m, 1H), 3.16-3.06 (m, 4H), 2.97 (s, 2H), 2.20-2.04 (m, 2H), 2.03-1.92 (m, 2H), 1.62-1.48 (m, 2H); ES-MS: 450.2 (M+1)+.

Provenance & Evidence