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Sodium hydride → HCID 22036242, 화합물

HRID 493356
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인쇄 미리보기

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HRID 493356 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][OH:8].[H-].[Na+].Cl[C:15]1[C:20]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[N:19][CH:18]=[CH:17][N:16]=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][O:8][C:15]1[C:20]([N:21]2[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]2)=[N:19][CH:18]=[CH:17][N:16]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 152273Phenol, 3-(2-hydroxyethoxy)-HCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

생성물 1

HCID 22036242HCID 22036242, 화합물수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
65 °C

실험 절차

To a stirred solution of 2-(3-hydroxyphenoxy)ethanol (7.71 g, 0.05 mol) in dry DMF (100 mL) at ˜0° C. (ice bath) was added NaH (3.90 g, 0 163 mol) in portions under N2. When the H2-evolution had ceased, a solution of 2-chloro-3-(4-tert-butoxycarbonyl-1-piperazinyl)pyrazine (0.05 mol, 14.9 g; from Example 52, Step 1) in dry DMF (70 mL) was added in one portion. The mixture was stirred at 65° C. for 1.75 h. After cooling, the reaction was quenched by addition of H2O in DMF. The mixture was filtered and concentrated. in vacuo. The residue was dissolved in EtOAc, washed with 1 M KHSO4 and water, dried (Na2SO4 +Norit), and concentrated in vacuo to give the title compound as a beige sticky oil. Yield 94%. This product was used directly in the next step without further purification.

후처리

  1. temperatureAfter cooling
  2. customthe reaction was quenched by addition of H2O in DMF
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with 1 M KHSO4 and water
  7. dry with materialdried (Na2SO4 +Norit)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-91ad27202abf454ea093186c8869896b
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07534794B2

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