Morpholine → (S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

HRID 75286Notes

Reaction equation

HRID 75286 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:13]([CH3:14])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C@@H:8]([NH2:10])[CH3:9].CC(C)([O-])C.[K+].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>COCCOC>[CH3:14][N:13]1[C:4]2[C:5](=[N:6][C:7]([C@@H:8]([NH2:10])[CH3:9])=[C:2]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:3]=2)[CH:11]=[CH:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 23665647Potassium tert-butoxideHCID 86707977(S)-1-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Product 1

HCID 86707976(S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(S)-1-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (1.6 g, 6.30 mmol) was stirred with potassium tert-butoxide (2.83 g, 25.2 mmol) and morpholine (6.58 g, 76 mmol) in DME (50 mL) at 88° C. for 4 hours. The mixture was then concentrated in vacuo. The residue was taken up in acetonitrile and water, and was lyophilized to give the title compound, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C14H20N4O, 261; found 261.

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-4cbd1736e79d42b396bc73bd97b79d20
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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