Trifluoroacetic acid → HCID 21106876, compound

Participants

Reaction Steps

To a stirred solution of 8-(3-{1-[(1-tert-butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid (14 g) in dichloroethane (100 mL) was added trifluoroacetic acid (30 mL) at 0° C. slowly. The resulting solution was stirred at 0° C. to room temperature for one hour. The solvent was removed in vacuo to yield yellow oil, which was dissolved in 20% IPA in dichloromethane and the solution was neutralized by sat. aq NaHCO3 resulting two clear phases, and the two phases were well shaken. The organic layer was separated, and the aqueous phase was extracted with 20% IPA/CH2Cl2. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give yellow solid (10 g), the solid was crystallized from methanol/water to give crystalline solid (8 g). ESI MS m/z 483.3 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.88 (d, J=10.0 Hz, 1H), 7.93 (s, 1H), 4.03-3.98 (m, 1H), 3.79-3.75 (m, 1H), 3.66-3.62 (m, 1H), 3.58-3.52(m, 1H), 3.47-3.44 (m, 2H), 3.05-2.88 (m, 4H), 2.62 (s, 3H), 2.49 (s, 3H), 2.35-2.23 (m, 3H), 2.06-2.02 (m, 1H), 1.70-1.58 (m, 2H), 1.51-1.44 (m, 1H), 0.93-0.64 (m, 8H).

Provenance & Evidence