Trifluoroacetic acid → HCID 178434453, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-oxopyrrolidine-3-carboxamide (22.3 mg, 0.046 mmol) and 2,2,2-trifluoroacetic acid (259.7 mg, 2.28 mmol). The reaction mixture was stirred at 60° C. until LC-MS showed that the starting material was consumed (8 hour). The CF3COOH was removed under reduced pressure and the residue purified by column (Silica gel, DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give the desired product (14.9 mg, 88.6%). HPLC: >99% purity, 1.91 min (254 nm); LRMS (APCI neg) m/e 368 (M−1). 1H NMR (400 MHz, CD3OD) δ 8.25 (d, J=5.6 Hz, 1H), 7.85 (dd, J=12.4, 2.4 Hz, 1H), 7.43 (m, 1H), 7.37 (t, J=8.8 Hz, 1H), 6.25 (dd, J=5.6, 0.8 Hz, 1H), 3.52-3.38 (m, 2H), 3.31 (m, 1H), 2.71 (s, 3H), 2.52-2.59 (m, 1H), 2.38-2.44 (m, 1H).

Provenance & Evidence