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5,6-Dimethylbenzimidazole → 2-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamate

HRID 724169
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HRID 724169 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:26][C:27]1[C:35]([CH3:36])=[CH:34][C:30]2[N:31]=[CH:32][NH:33][C:29]=2[CH:28]=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:31]3[C:30]4[CH:34]=[C:35]([CH3:36])[C:27]([CH3:26])=[CH:28][C:29]=4[N:33]=[CH:32]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6755,6-DimethylbenzimidazoleHCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

생성물 1

HCID 213004172-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamate수율 22%

시약·촉매·용매 2

HCID 8895Cupric acetate
촉매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)oxy]ethyl}phenylboronic acid (100 mg, 0.28 mmol), 5,6-dimethylbenzimidazole (40 mg, 0.28 mmol), Cu(OAc)2 (60 mg, 0.33 mmol), triethylamine (115 μl, 0.83 mmol), MS4A (100 mg), and CH2Cl2 (4 ml) was stirred at room temperature for 1 week. After filtration through a bed of celite, the filtrate was diluted with CH2Cl2, and washed with water. The organic fraction was dried over MgSO4 and filtered. After concentration under reduced pressure, the residue was purified by preparative TLC (CH2Cl2/MeOH=10/1) to afford 28 mg (22%) of the title compound.

후처리

  1. filtrationAfter filtration through a bed of celite
  2. additionthe filtrate was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic fraction was dried over MgSO4
  5. filtrationfiltered
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by preparative TLC (CH2Cl2/MeOH=10/1)

출처 및 근거

ORD 기록
ord-8b3d909bc9494d0787c1fff36e4418a8
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141580B2

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