Réaction #744083

Équation de réaction

NaBH(OAc)3

1-[2-(4-amino-1-piperidinyl)ethyl]-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one

6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde

CHCl3

MeOH

→

title compound

Rendement 26.0%

1-(2-{4-[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]-1-piperidinyl}ethyl)-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one Dihydrochloride

Rendement 26.0%

Conditions de réaction

Traitement

1. 1
   Autreat rt
2. 2
   AutreAfter which it was purified by chromatography on silica gel using a 0-30% MeOH in DCM gradient

Mode opératoire

1-[2-(4-amino-1-piperidinyl)ethyl]-8-ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one (0.117 g, 0.368 mmol) and 6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde (0.061 g, 0.368 mmol) were dissolved in CHCl3 (2 ml) and MeOH (0.2 ml) at rt under argon. NaBH(OAc)3 (0.234 g, 1.10 mmol) was added and the reaction was allowed to stir at rt for 16 h. After which it was purified by chromatography on silica gel using a 0-30% MeOH in DCM gradient to give the free base of the title compound as a clear oil (0.045 g, 26%).

Source