Ethyl bromoacetate → Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

HRID 657102노트

반응식

HRID 657102 반응식
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][NH:5][C:6]1[C:11]([NH:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1

참가 물질

6

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86635355N2-[2,2-Bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine

생성물 1

HCID 68811995Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A mixture of N2-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine (2.2 g, 10 mmol), ethyl bromoacetate (1.1 mL, 1.65 g, 10 mmol) and potassium carbonate (2.1 g, 20 mmol) in acetonitrile (50 mL) and DMF (5 mL) was stirred at room temperature overnight. The mixture was filtered and evaporated. The residue was dissolved in ethyl acetate and washed with water and brine. The organic extract was concentrated and added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%).

후처리

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. extractionThe organic extract
  6. concentrationwas concentrated
  7. additionadded to a silica column which
  8. washwas then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%)

출처 및 근거

ORD 기록
ord-c9089bf87fd34a388c34d7ae86ad33e5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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