Potassium Carbonate → ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-piperidinyl]amino}2-pyrazinyl)acrylate

HRID 226367노트

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HRID 226367 반응식
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.C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH2:36])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36][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)[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 22831369(R)-1-benzyl-3-Aminopiperidine DihydrochlorideHCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

생성물 1

HCID 86603672ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-piperidinyl]amino}2-pyrazinyl)acrylate수율 24.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (300 mg) and potassium carbonate (4.94 mg) in DMF (15 mL) was added (3R)-1-benzyl-3-piperidinamine dihydrochloride (668 mg) under nitrogen at ambient temperature and the mixture was stirred at 85° C. for 18 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform-MeOH=97-3) to give ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-piperidinyl]amino}2-pyrazinyl)acrylate (125 mg) as an oil.

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform-MeOH=97-3)

출처 및 근거

ORD 기록
ord-a1cd390e29ec4101b5ede8d540346e4d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

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