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Acetic Acid → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

HRID 1657313
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HRID 1657313 반응식
[NH2:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]=1[CH3:9])[CH3:3].[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:41])=[O:40])[C:31]=1[CH2:48][CH:49]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:41])=[O:40])[C:31]=1[CH2:48][CH2:49][NH:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:8]=1[CH3:9])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 104066724-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazoleHCID 104257273-Methyl-1-(phenylsulfonyl)-2-indoleacetaldehyde

생성물 1

HCID 102588713-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole수율 71.3%

시약·촉매·용매

2
HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of 4-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazole (735 mg), 3-methyl-1-(phenylsulfonyl)-2-indoleacetaldehyde (626 mg) and molecular sieves 3A (100 mg) in dry methanol (30 ml) was stirred at ambient temperature for 30 minutes. Acetic acid (0.35 ml) and sodium cyanoborohydride (126 mg) were added and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was treated with cold water, extracted twice with ethyl acetate, which was washed with brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was chromatographed over silica gel (eluted with 3% methanol in chloroform) to give 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole (947 mg) as an amorphous powder.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionextracted twice with ethyl acetate, which
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed over silica gel (eluted with 3% methanol in chloroform)

출처 및 근거

ORD 기록
ord-18c52c36fedb4a1f9f9ffebd6e8d84cb
출처 데이터셋
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05256780

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