Réaction #744082

Équation de réaction

NaBH(OAc)3

NaHCO3

triethylamine

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

3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

→

title compound

Rendement 75.0%

1-(2-{4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}ethyl)-7-(methyloxy)-1,5-naphthyridin-2(1H)-one Hydrochloride

Rendement 75.0%

Solvants

chloroform

MeOH

Conditions de réaction

Traitement

1. 1
   ExtractionThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
2. 2
   AutreThe combined organic phases were dried
3. 3
   Autreevaporated
4. 4
   Autrethe crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient

Mode opératoire

A mixture of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-(methyloxy)-1,5-naphthyridin-2(1H)-one dihydrochloride (174 mg, 0.466 mmol) in chloroform (5 ml) and MeOH (0.1 ml) was treated with triethylamine (205 μl, 1.484 mmol) and stirred for 0.25 h before addition of 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 126(e)) (69 mg, 0.424 mmol). The reaction was stirred for 0.5 h before addition of NaBH(OAc)3 (270 mg, 1.272 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the free base of the title compound (157 mg, 75%).

Source