HCID 57975902, compound → HCID 178489399, compound

Participants

Reaction Steps

2-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (103 mg, 0.14 mmol) obtained in step 1 was dissolved in 1 ml of a 5% v/v solution of 70% perchloric acid in acetic acid and stirred overnight at room temperature. The crude was filtered and purified by reverse phase HPLC, lyophilized to afford pyrrolidine-2-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-amide (24 mg, 35% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.76 (m, 2H), 1.91 (m, 1H), 2.19 (m, 1H), 2.89 (m, 1H), 2.95 (d, 6H), 3.01 (m, 1H), 3.10 (m, 1H), 3.85 (s, 3H), 7.10 (m, 1H), 7.22 (d, 1H), 7.47 (m, 1H), 7.65 (d, H), 7.72 (s, 1H), 7.83 (d, 1H), 7.96 (m, 1H), 8.36 (s, 1H), 8.88 (s, 1H). MS: m/z 485.1 (M+H+).

Provenance & Evidence