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

HRID 2354098Notes

Reaction equation

HRID 2354098 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[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([O-])=O)[CH2:14]2)=[N:10][CH:11]=1.[ClH:22]>ClCCCl.O1CCOCC1>[ClH:22].[ClH:22].[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:21])=[N:7][CH:8]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86628131(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 2

HCID 111,2-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate (10.50 g) in 1,2-dichloroethane (100 mL) was added a 4N HCl in dioxane (100 mL) and the mixture was stirred at 20-25° C. for 2 hours under nitrogen atmosphere to give a solid. The solid was collected by filtration to give methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (9.73 g).

Workup

  1. customto give a solid
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-712374906f7e4ace8513e72c11bbd472
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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