Pyridine → 5-Benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

HRID 1108587노트

반응식

HRID 1108587 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH3:18])[C:11](=[O:19])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>ClCCl>[CH2:30]([O:29][C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH3:18])[C:11](=[O:19])[CH2:10]2)=[C:6]([F:8])[CH:7]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 187839025-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

생성물 1

HCID 187839065-Benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-20 °C

실험 절차

5-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene (3.5 g) was dissolved in dry dichloromethane (50 ml) under argon. Pyridine (1.33 ml) was added, and the mixture cooled to -20° C. Benzyl chloroformate (2.06 ml) was added, and the mixture stirred for 10 minutes at -20° C., before allowing the temperature to rise to ambient over 1.5 hours. Solvents were evaporated, the residue dissolved in dichloromethane and washed with sodium bicarbonate solution. After drying (MgSO4) and evaporation of solvent, the residue was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 4% methanol in dichloromethane. Relevant fractions were combined and evaporated to give 5-benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene (3.28 g).

후처리

  1. waitto ambient over 1.5 hours
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with sodium bicarbonate solution
  5. customAfter drying
  6. custom(MgSO4) and evaporation of solvent
  7. customthe residue was chromatographed on silica
  8. temperaturea gradient increasing in polarity from 0 to 4% methanol in dichloromethane
  9. customevaporated

출처 및 근거

ORD 기록
ord-63f7b243b9444ded82b59f57879b9c03
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069145

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