Ethanol → HCID 67494484, compound

Participants

Reaction Steps

Sodium cyanoborohydride (3.5 equiv) was added to a stirring mixture of aldehyde, 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (1 equiv) and 1-benzylpiperidin-4-yl)methanamine (2 equiv) in ethanol and acetic acid at room temperature. When the reaction was deemed complete by HPLC, LC-MS, or TLC analysis, the mixture was quenched with saturated aqueous sodium bicarbonate, then extracted with dichloromethane (2×). The combined organics were dried over sodium sulfate, filtered, concentrated to dryness, and purified on silica gel to afford the desired product, N5-((1-benzylpiperidin-4-yl)methyl)-3-(6-fluoroquinolin-3-yl)-N7,N7-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidine-5,7-diamine.

Provenance & Evidence