Trifluoroacetic acid → HCID 66967104, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.5 mL) was added to a solution of (E)-7-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)-carbamoyl]-vinyl}-2-oxo-2,3-dihydro-1H-pyrido[2,3-b]pyrazine-4-carboxylic acid tert-butyl ester in CH2Cl2 (1 mL) at 10° C. After stirring 1 hr, volatiles were removed in vacuo and the resulting residue was dissolved in EtOAc (2 mL). Upon addition of dilute NaOH, a precipitate formed. The solid was collected by filtration, washed with water (100 mL), MeOH (50 mL), EtOAc (50 mL) and CH2Cl2 (50 mL) to afford the title compound (170 mg). 1H NMR (300 MHz, DMSO-d6) δ 10.42 and 10.33 (rotamers, 2s, br, 1H), 7.90 (m, 1H), 7.45 (m, 3H), 7.22 (m, 1H), 7.12 (m, 1H), 6.83 (d, J=15.4 Hz, 1H), 6.42 and 6.17 (rotamers, 2s, 1H), 4.98 and 4.84 (rotamers, 2s, 2H), 3.99 and 3.95 (rotamers, 2s, 2H), 3.72 and 3.68 (rotamers, 2s, 3H), 3.07 and 3.00 (rotamers, 2s, 3H). MS (ESI) m/e: 376 (M+H)+.

Provenance & Evidence