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4-(Chloromethyl)-1-trityl-1H-imidazole → 4-[6-(4-Cyano-phenyl)-2-oxo-3,3-bis-(1-trityl-1H-imidazol-4-ylmethyl)-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide

HRID 1355661
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HRID 1355661 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][C:14](=[O:31])[N:15]3[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:33][C:34]1[N:35]=[CH:36][N:37]([C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH2:33][C:34]4[N:35]=[CH:36][N:37]([C:39]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[CH:38]=4)([CH2:33][C:34]4[N:35]=[CH:36][N:37]([C:39]([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)[CH:38]=4)[C:14](=[O:31])[N:15]3[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:29])[CH3:30])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 185077664-[6-(4-Cyano-phenyl)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide

생성물 1

HCID 867590514-[6-(4-Cyano-phenyl)-2-oxo-3,3-bis-(1-trityl-1H-imidazol-4-ylmethyl)-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide수율 55.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-[6-(4-Cyano-phenyl)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide (216 mg, 0.501 mmol) and 4-chloromethyl-1-trityl-1H-imidazole compound (402 mg, 1.12 mmol) were dissolved in 5 ml of anhydrous THF under an atmosphere of dry N2. To this solution was added 95% potassium hexamethyldisilylamide (KHMDS) (230 mg, 1.10 mmol) and the reaction mixture was subsequently stirred overnight. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3. The DCM layer was dried over sodium sulfate (Na2SO4), filtered and concentrated under vacuum to give a purple foam which was chromatographed on flash silica gel eluting with a gradient of chloroform (CHCl3) to CHCl3/MeOH/NH4OH (98/2/0.01) to give 300 mg of the titled compound as a pink oil.

후처리

  1. customThe reaction mixture was partitioned between DCM and saturated aqueous NaHCO3
  2. dry with materialThe DCM layer was dried over sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a purple foam which
  6. customwas chromatographed on flash silica gel eluting with a gradient of chloroform (CHCl3) to CHCl3/MeOH/NH4OH (98/2/0.01)

출처 및 근거

ORD 기록
ord-6949ed96647d4bf0805c89b12c89ee9c
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06586447B1

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