Diisopropyl Ether → methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl)acrylate dihydrochloride

HRID 226406Notes

Reaction equation

HRID 226406 reaction equation
[CH3:1][O:2][C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[N:7]=[CH:8][C:9]([NH:12][C@@H:13]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)=[N:10][CH:11]=1.[ClH:26].O1CCOCC1.C(OC(C)C)(C)C>O1CCOCC1>[ClH:26].[ClH:26].[NH:15]1[CH2:16][CH2:17][C@@H:13]([NH:12][C:9]2[N:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:25])=[N:7][CH:8]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 67128781tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate

Product 1

HCID 67129309methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl)acrylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate (830 mg) in dioxane (8.3 mL) was added 4N HCl/dioxane (6.0 mL), which was stirred at room temperature for 1 hour. To the reaction mixture was added diisopropylether, and the precipitate was filtered to give methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (742 mg) as a yellow powder.

Workup

  1. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-62314b6a887345feaf8f5bfd194fa4ff
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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