Diisopropylethylamine → HCID 58024751, compound

Participants

Reaction Steps

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 2.4 g, 6.3 mmol) was added to a solution of 4-[(8-bromooctanoyl)amino]benzoic acid (2.1 g, 6.1 mmol) in N,N-dimethylformamide (20 ml) followed by N,N-diisopropylethylamine (2.5 g, 19 mmol). The solution was stirred at room temperature for 15 min, and 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.7 g, 5.6 mmol. e.g. which can be substantially as prepared in Intermediate 7 including alternative preparation no. 1 thereof) was added as a solid. The solution was stirred at room temperature for 3 hours, and then was added to aqueous sodium bicarbonate solution (200 ml) and extracted with dichloromethane (2×100 ml). The dried (sodium sulphate) organic extract was evaporated gently to leave crude 4-[(8-bromooctanoyl)amino]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide mixed with N,N-dimethylformamide (about 5 ml).

Provenance & Evidence