N,N-Dimethylaniline → 5-Benzyloxycarbonylamino-2-(4-methyl-3-oxopiperazin-1-yl)fluorobenzene

HRID 1108570노트

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HRID 1108570 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11](=[O:16])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.CN(C)C1C=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]>CN(C=O)C.C(OCC)(=O)C>[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]([CH3:15])[C:11](=[O:16])[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

6

반응물 3

HCID 949N,N-DimethylanilineHCID 10387Benzyl chloroformateHCID 187839304-(4-Amino-2-fluorophenyl)-1-methylpiperazin-2-one

생성물 1

HCID 187839085-Benzyloxycarbonylamino-2-(4-methyl-3-oxopiperazin-1-yl)fluorobenzene

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
-20 °C

실험 절차

5-Amino-2-(4-methyl-3-oxopiperazin-1-yl)fluorobenzene (2.94 g) was dissolved in dry DMF (40 ml) under argon, and the solution cooled to -20° C. N,N-Dimethylaniline (2.1 ml) was added, followed by benzyl chloroformate (2.07 ml), and the mixture stirred for 10 minutes at -20° C. The temperature was allowed to rise to ambient over 16 hours. The mixture was diluted with ethyl acetate, and washed twice with water, and then brine. After drying (MgSO4) and evaporation of solvent, the residue was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give 5-benzyloxycarbonylamino-2-(4-methyl-3-oxopiperazin-1-yl)fluorobenzene (4.6 g).

후처리

  1. waitto ambient over 16 hours
  2. washwashed twice with water
  3. customAfter drying
  4. custom(MgSO4) and evaporation of solvent
  5. customthe residue was chromatographed on silica
  6. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  7. customevaporated

출처 및 근거

ORD 기록
ord-d748b4cf864242f8a1950bc12750be38
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069145

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