3-(Dimethylamino)-1-propanol → N-Cyclopropyl-3-(2-((6-(3-(dimethylamino)propoxy)pyridin-3-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

HRID 907265Notes

Reaction equation

HRID 907265 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].CC(C)([O-])C.[K+].Br[C:15]1[N:20]=[CH:19][C:18]([CH2:21][N:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:32]4[CH:33]=[C:34]([CH:41]=[CH:42][C:43]=4[CH3:44])[C:35]([NH:37][CH:38]4[CH2:40][CH2:39]4)=[O:36])[CH:28]=3)[C:23]2=[O:45])=[CH:17][CH:16]=1>C1COCC1>[CH:38]1([NH:37][C:35](=[O:36])[C:34]2[CH:41]=[CH:42][C:43]([CH3:44])=[C:32]([C:27]3[CH:28]=[C:29]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:45])[N:22]([CH2:21][C:18]3[CH:19]=[N:20][C:15]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[CH:16][CH:17]=3)[CH:31]=[CH:30]4)[CH:33]=2)[CH2:39][CH2:40]1

Participants

5

Reactant 3

HCID 766463-(Dimethylamino)-1-propanolHCID 23665647Potassium tert-butoxideHCID 575517913-(2-((6-Bromopyridin-3-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 25019959N-Cyclopropyl-3-(2-((6-(3-(dimethylamino)propoxy)pyridin-3-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To solution of 3-(dimethylamino)propan-1-ol (0.03 mL) in THF (1 mL) was added potassium tert-butoxide (28 mg) and the reaction stirred at room temperature for 10 minutes. A solution of the product of step i) (100 mg) in THF (2 mL) was added, and the mixture heated at reflux for 100 hours.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 100 hours

Sources & evidence

ORD record
ord-b31c8877c17f4865a849925393a56209
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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