Piperidine → 4-[1-Ethyl-7-((R)-2-piperazin-1-ylmethyl-cyclopentylmethyl)-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamine

Participants

Reaction Steps

The product of example 191 step 1 (100 mg, 0.387 mmol) was dissolved in 1,2-dichloroethane (2.5 ml) and added to a stirred solution of the product of Step 1 (480 mg, 0.774 mmol) and diisopropyl ethylamine (100 mg, 0.774 mmol) in 1,2-dichloroethane (2.5 ml). After stirring for 5 minutes the reaction was treated with sodium triacetoxyborohydride (164 mg, 0.774 mmol) and the reaction was stirred for 16 hours at room temperature. The reaction was then treated with piperidine (5 ml) and stirred for 5 hours at room temperature. The solvent was then evaporated in vacuo and the residue diluted with dichloromethane, washed with saturated sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulfate and evaporated iv vacuo. The residue was purified by automated reverse phase chromatography (Biotage flex, acetonitrile/water eluant) to afford the title compound (30 mg, 19%); MS (ES+), m/e 412 [M+H]+.

Provenance & Evidence