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Chloroform → 5-[1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-(4-methanesulfonyl-piperazin-1-yl)-thiazol-4-one

HRID 1012203
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HRID 1012203 반응식
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18][C:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:16][C:15]2=[O:25])=[CH:9][C:8]=1[O:26][CH3:27].C(Cl)(Cl)Cl.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[F:37][C:2]([F:36])([F:1])[C:3]1[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=[CH:28][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18][C:17]([N:19]3[CH2:20][CH2:21][N:22]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:23][CH2:24]3)=[N:16][C:15]2=[O:25])=[CH:9][C:8]=1[O:26][CH3:27]
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참가 물질

5

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HCID 6212ChloroformHCID 31297Methanesulfonyl chlorideHCID 730441835-[1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-piperazin-1-yl-thiazol-4-one

생성물 1

HCID 730639735-[1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-(4-methanesulfonyl-piperazin-1-yl)-thiazol-4-one수율 52%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
60 °C

실험 절차

To a flask was added 5-[1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-piperazin-1-yl-thiazol-4-one (50 mg, 92 μmol) (from Example 23) chloroform (5 mL), methyl sulfonyl chloride (3 equiv, 32 μL) and TEA (3 equiv, 40 μL). The reaction was stirred at 60° C. under N2. The reaction solution was diluted with DCM (70 mL), washed with aq NH4Cl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 90:10) to provide the title compound as a white solid (30 mg, 52%). 1H NMR (DMSO-d6) δ 7.99 (2H, s), 7.94 (1H, s), 7.62 (1H, s), 7.18 (1H, s), 7.13 (1H, dd, J1=2.0 Hz, J2=8.4 Hz), 7.01 (1H, d, J=8.4 Hz), 5.37 (2H, s), 4.06 (2H, m), 3.88 (3H, s), 3.74 (2H, m), 3.31-3.36 (4H, m), 2.85 (3H, s); MS (ESI) 624 (MH+).

후처리

  1. washwashed with aq NH4Cl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 90:10)

출처 및 근거

ORD 기록
ord-b73934178fc94b4a97de91dea04f68c6
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977489B2

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