Ethyl Acetate → (2R)-4-[(4-chlorophenyl)sulfonyl]-2-methyl-1-(2-pyridinylcarbonyl)piperazine

HRID 41315

반응식

HRID 41315 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C@H:13]([CH3:17])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](Cl)=[O:31].C(OCC)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)=[O:31])[C@H:13]([CH3:17])[CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135034Pyridine-2-carbonyl chlorideHCID 11630465(3R)-1-[(4-chlorophenyl)sulfonyl]-3-methylpiperazine

생성물 1

HCID 44612083(2R)-4-[(4-chlorophenyl)sulfonyl]-2-methyl-1-(2-pyridinylcarbonyl)piperazine수율 45.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

To a solution of (3R)-1-[(4-chlorophenyl)sulfonyl]-3-methylpiperazine (0.15 g, 0.55 mmol) in dry acetonitrile (5 mL) was added potassium carbonate (90 mg, 0.66 mmol) and 2-pyridinecarbonyl chloride (106 mg, 0.60 mmol) and the reaction mixture heated at 85° C. for 24 h. To the mixture was added ethyl acetate (30 mL) and the organic phase washed with 10% aqueous sodium bicarbonate (50 mL) before it was dried (MgSO4), filtered and the solvent evaporated. The crude product was purified by Biotage SP4 (12+M silica column) eluting 0-4% MeOH in DCM to give the title compound as an off-white solid (95 mg).

후처리

  1. washthe organic phase washed with 10% aqueous sodium bicarbonate (50 mL) before it
  2. dry with materialwas dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe crude product was purified by Biotage SP4 (12+M silica column)
  6. washeluting 0-4% MeOH in DCM

출처 및 근거

ORD 기록
ord-626bff4e6de04ebe8ef8b3da38d7a452
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530478B2

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