Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 3-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide

Participants

Reaction Steps

To 3-{[[(3-bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acid (150 mg, 0.390 mmol) in DCM 7.8 mL) was added 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (133 mg, 0.390 mmol), HBTU (163 mg, 0.429 mmol), and TEA (0.163 mL, 1.171 mmol). This mixture was stirred at room temperature for 2 h. The reaction mixture was washed with H2O (2×3 mL), dried over Na2SO4, filtered, and concentrated. The crude product was further purified by CombiFlash flash chromatograph to afford the title compound (0.2453 mg, 94%). LC-MS m/z 669 (M+H)+.

Provenance & Evidence