Water → HCID 67128878, compound

HRID 2354092Notes

Reaction equation

HRID 2354092 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.[C:17]12([CH2:24][N:25]3[CH2:29][CH2:28][C@@H:27]([NH2:30])[CH2:26]3)[O:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.CCN(CC)CC.O>CC(N(C)C)=O>[C:17]12([CH2:24][N:25]3[CH2:29][CH2:28][C@@H:27]([NH:30][C:2]4[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=4)[CH2:26]3)[O:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67128668HCID 67128668, compoundHCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

Product 1

HCID 67128878HCID 67128878, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of ethyl (2E)-3-(5-chloropyrazin-2-yl)acrylate (242.8 mg) in DMA (1.9 mL) was added (3R)-1-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)pyrrolidin-3-amine dihydrochloride (370 mg) and Et3N (796 uL), which was stirred at 100° C. for 24 hours. To the resultant was added H2O, which was extracted with AcOEt. 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-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (425 mg) as a brown solid.

Workup

  1. extractionwas extracted with AcOEt
  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-d2428a02ba05420ba912df114e0a5722
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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