Cyano-borohydride → (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Steps

A vial was charged with (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate (Example 233, 700 mg, 1.14 mmol) and morpholin-4-yl-acetaldehyde monohydrate hydrochloride (250 mg, 1.37 mmol) in methanol (10 mL). MP-cyanoborohydride (730 mg, 1.71 mmol) beads were added and the resulting mixture was allowed to stir at room temperature overnight. The reaction mixture was filtered and the beads were washed with more methanol. The filtrate was concentrated under reduced pressure and purified by Analogix SF15-24 g in dichloromethane/methanol system to give a light yellow solid (320 mg, 38.6%).

Provenance & Evidence