Diisopropylethylamine → HCID 53468256, compound

Participants

Reaction Steps

A solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (150 mg, 0.495 mmol), (3,5-difluorophenyl)acetic acid (85 mg, 0.495 mmol), HATU (188 mg, 0.495 mmol), DIEA (0.346 mL, 1.982 mmol) was stirred at room temperature over the weekend. At this time, LCMS analysis indicated complete conversion, so the reaction mixture was poured into water (10 mL), whereupon a beige precipitate formed. The precipitate was filtered, suspended in DCM-methanol and dry-loaded onto silica, then purified by flash chromatography (0-10% methanol in DCM) to afford 3-{1-[(3,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (150 mg, 0.357 mmol, 72.0% yield) as a white solid. LC-MS (ES) m/z=421 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.27 (m, 2H), 3.94 (s, 3H), 3.97 (s, 2H), 4.18-4.32 (m, 2H), 7.02-7.09 (m, 2H), 7.11-7.20 (m, 1H), 7.41-7.47 (m, 1H), 7.50-7.55 (m, 1H), 8.12-8.22 (m, 1H), 8.25 (s, 1H). Note: NH's are not observed as individual peaks.

Provenance & Evidence