Trifluoroacetic acid → HCID 59304358, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing (S)—N-(4-(1-(4-methoxybenzyl)-3-(3-(dimethylamino)pyrrolidin-1-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (14 mg, 0.02 mmol) at ambient temperature under a drying tube was added TFA (1 mL), and the reaction mixture was heated at 50° C. overnight. After cooling, the reaction was concentrated to dryness and then redissolved in 5 mL dichloromethane, to which 5 mL of 10% sodium carbonate was added. After stirring for a few minutes, the layers were separated and the organics were washed with 10% sodium carbonate. The organics were dried (MgSO4), filtered and concentrated to a crude oil. Biotage 12S with step gradient of dichloromethane (100 mL), 5/95 MeOH/dichloromethane (100 mL), and 9/1 dichloromethane/MeOH (200 mL) eluted the product. The product containing fractions were pooled and concentrated to a yellow solid (4.2 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 11.83 (br s, 1H), 8.41 (d, 1H), 8.23 (m, 1H), 7.96 (m, 1H), 7.60 (m, 2H), 7.40 (m, 1H), 7.24 (m, 2H), 6.16 (d, 1H), 3.82 (m, 1H), 3.72 (m, 2H), 3.56 (m, 1H), 2.87 (m, 1H), 2.30 (s, 6H), 2.20 (m, 1H), 1.94 (m, 1H). LCMS (APCI+): m/z 573 (M+1) detected.

Provenance & Evidence