Sodium cyanoborohydride → HCID 68803960, compound

Participants

Reaction Steps

A representative example of method E is as follows. Preparation of 5-[3-(8-Bromo-6-chloro-1,2,3,4-tetrahydro-quinolin-4-ylamino)-propylamino]-4H-thieno[3,2-b]pyridin-7-one: A solution of 5-(3-Amino-propylamino)-4H-thieno[3,2-b]pyridine-7-one di-hydrochloride (XVIII) in methanol (0.08M) was prepared and then treated with sodium methoxide (2 equivalents, 0.5M in methanol). 8-Bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one (1 equivalent) was added as a solid. Sodium cyanoborohydride (3 equivalents) was added as a solid. The mixture was then refluxed for 20 hours, adding an additional equivalent of sodium cyanoborohydride after 16 hours. The reaction mix was poured onto a column of silica gel and the product was eluted with 10% NH3 (sat.)/MeOH and dichloromethane. Solvent was then removed in vacuo. Purification of the crude product was accomplished by flash chromatography, product eluted with a gradient of 0-12% NH3 (sat.)/MeOH and dichloromethane. The resulting solid was triturated with ether, isolated by filtration, and dried to give the title compound as a white solid (formula XIX, X═NH).

Provenance & Evidence