Réaction #744221

Équation de réaction

sodium triacetoxyborohydride

1-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinone

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

DCM

sodium carbonate

→

title compound

Rendement 20.0%

1-[2-((3S,4S)-3-{[(6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)amino]methyl}-4-hydroxy-1-pyrrolidinyl)ethyl]-7-(methyloxy)-2(1H)-quinolinone hydrochloride

Rendement 20.0%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 1 h
2. 2
   ConcentrationThe reaction mixture was concentrated
3. 3
   Autrepurified

Mode opératoire

1-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-(methyloxy)-2(1H)-quinolinone (118 mg, 0.372 mmol) and 6,7-dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde (68 mg, 0.409 mmol) were combined in anhydrous DCM (5 ml) and anhydrous MeOH (1 ml) with a spatula of solid sodium carbonate. The reaction mixture was stirred under nitrogen for 18 h then sodium triacetoxyborohydride (247 mg, 1.12 mmol) was added and stirred for 1 h. The reaction mixture was concentrated and purified to obtain the free base of the title compound as a pale oil (35 mg, 20%) after column:chromatography (90:10:1: DCM:MeOH:NH4OH).

Source