Trifluoroacetic acid → HCID 178434459, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 1-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-3-(pyridin-2-yl)urea (21.3 mg, 0.0427 mmol) from Example 20, Step A and 2,2,2-trifluoroacetic acid (487 mg, 4.27 mmol). The reaction mixture was stirred at 80° C. for 8 hours. The CF3COOH was removed under reduced pressure and the residue was purified by column chromatography (Silica gel, DCM/7M NH3 in MeOH from 50/1 to 10/1, v/v) to provide the product (14 mg, 85%). LRMS (APCI−): 100% purity, 220 nm, m/z 377 (M−1) detected; 1H NMR (400 MHz, CD3OD-d4) δ 8.31 (m, 1H), 8.25 (d, J=5.6 Hz, 1H), 7.83 (m, 1H), 7.75 (m, 1H), 7.36 (m, 2H), 7.21 (d, J=8.4 Hz, 1H), 7.04 (m, 1H), 6.28 (d, J=5.6 Hz, 1H), 2.72 (s, 3H)

Provenance & Evidence