Trifluoroacetic acid → Ammonium Hydroxide

Participants

Reaction Steps

A solution od 8-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (217 mg, 0.38 mmol), DCM (5 mL), and TFA (5 mL) is stirred at rt for 2 h. At that point the solution is concentrated in vacuo and the residue is separated via semi-prep HPLC(C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound. MS (ESI) m/z 468.1 (M+1); 1H NMR (400 MHz, DMSO-do) δ ppm 10.39 (s, 1 H), 8.51 (s, 1 H), 8.28 (d, J=9.1 Hz, 1 H), 8.06-8.15 (m, 2 H), 7.97 (d, J=8.6 Hz, 1 H), 7.65 (t, J=8.0 Hz, 1 H), 7.43-7.53 (m, 2 H), 7.13 (dd, J=9.0, 2.4 Hz, 1 H), 6.80 (d, J=3.5 Hz, 1 H), 4.19 (q, J=6.6 Hz, 1 H), 3.34-3.42 (m, 1 H), 3.08-3.20 (m, 1 H), 2.88 (t, J=5.7 Hz, 2 H), 1.49 (d, J=7.1 Hz, 3 H).

Provenance & Evidence