Réaction #8366

Équation de réaction

potassium sodium tartrate

3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester

dimethylamine

methanol

trimethylaluminum

hexane

→

title compound

N,N-Dimethyl-3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionamide

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreThe organic portion is separated
2. 2
   Lavagewashed with water and brine
3. 3
   Séchagedried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue is chromatographed on SiO2 (10% methanol in dichloromethane)

Mode opératoire

To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester (0.30 g, 0.73 mmol) and 2M dimethylamine in methanol (1.05 mL, 2.1 mmol) in dichloromethane (1 mL) is added 2 M trimethylaluminum in hexane (1.64 mL, 3.25 mmol). The solution is heated at 40° C. for 48 h. The mixture is diluted with dichloromethane (150 mL), treated with saturated potassium sodium tartrate (30 mL), and stirred 18 h. The organic portion is separated and; washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (10% methanol in dichloromethane) to yield the title compound, 0.29 g (89%), as a yellow foam.

Source