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

HRID 1108587ノート

反応式

HRID 1108587 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-63f7b243b9444ded82b59f57879b9c03
出典データセット
uspto-grants-2000_05
特許番号
US06069145

反応ノート

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