Water → HCID 86603708, compound

HRID 2376086Notes

Reaction equation

HRID 2376086 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.Cl.Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[CH2:22][N:23]1[CH2:27][CH2:26][C@@H:25]([NH2:28])[CH2:24]1.C([O-])([O-])=O.[K+].[K+].O>CN1CCN(C)C1=O>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[CH2:22][N:23]1[CH2:27][CH2:26][C@@H:25]([NH:28][C:2]2[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=2)[CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 53256448HCID 53256448, compoundHCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

Product 1

HCID 86603708HCID 86603708, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
106 °C

Procedure

To a mixture of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (278 mg) in 1,3-dimethyl-2-imidazolidinone (2.78 mL) was added (3R)-1-(3-methoxybenzyl)-3-pyrrolidinamine dihydrochloride (547.5 mg) and K2CO3 (1.08 g), which was stirred at 106° C. for 3 hours. To the resultant was added H2O, which was extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-(3-methoxybenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (367.5 mg) as a brown solid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-234ded24e91e4f1ca5f924c453f712b6
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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