2-bromo-N-(pyrazin-2-yl)acetamide → 3-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-pyrrolidinium bromide

HRID 389911Notes

Reaction equation

HRID 389911 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)=[O:4].[OH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH3:18])[C:14]1=O>C(#N)C>[Br-:1].[OH:12][CH:13]1[CH2:17][CH2:16][N+:15]([CH3:18])([CH2:2][C:3](=[O:4])[NH:5][C:6]2[CH:11]=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 445426692-bromo-N-(pyrazin-2-yl)acetamide2×HCID 69033113(3R)-3-hydroxy-1-methyl-pyrrolidin-2-one

Product 1

HCID 867617703-Hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-pyrrolidinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-Bromo-N-pyrazin-2-yl-acetamide (Intermediate A)(3.0 g, 13.9 mmol) in acetonitrile (80 ml) is treated with (R)-hydroxy-methyl pyrrolidone (1.4 g, 13.9 mmol). The resulting suspension is stirred at room temperature for 3 hours and then filtered. The solid is washed with acetonitrile and dried in vacuo overnight to yield the titled compound as a brown solid.

Workup

  1. filtrationfiltered
  2. washThe solid is washed with acetonitrile
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-316d80e5adb94f3f8f144316b110b54e
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

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