Diisopropylethylamine → HCID 178497938, compound

Participants

Reaction Steps

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound 1c (0.3 g, 1.17 mmol), 2,3-diamino-benzoic acid methyl ester Compound 8a (3.43 g, 20.64 mmol), HATU (7.85 g, 20.66 mmol), DIPEA (8.64 mL, 62 mmol) in DMF (250 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes) to yield 2-amino-3-[(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)-amino]-benzoic acid methyl ester Compound 8b (5.1 g, 63% yield) as a colorless gel. 1H NMR (300 MHz, CD3OD) δ 9.03 (d, 1H, J=2.1 Hz), 8.78 (d, 1H, J=2.1 Hz), 7.58 (d, 1H, J=7.8 Hz), 7.26 (d, 1H, J=7.8 Hz), 7.15 (t, 1H, J=7.8 Hz), 3.49 (s, 3H); MS (ESI) m/z: 391 (M+H+).

Provenance & Evidence