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Triethylamine → 2-[4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 891170
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HRID 891170 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:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:30][NH:29][N:28]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[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:29]3[CH:30]=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:27]([CH3:26])=[N:28]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acidHCID 178434528HCID 178434528, 화합물

생성물 1

HCID 865909252-[4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate수율 21.4%

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 (200 mg, 0.55 mmol), 3-methyl-4-phenylpyrazole (87 mg, 0.55 mmol), Copper(II) acetate (120 mg, 0.66 mmol), triethylamine (0.23 mL, 1.65 mmol), molecular sieves 4A (200 mg), and dichloromethane (8 mL) was stirred at room temperature for 3 days. After filtration through a bed of celite, the filtrate was diluted with dichloromethane, and washed with water. The organic fraction was dried over MgSO4. After concentration under reduced pressure, the residue was purified by TLC with dichloromethane/ethylacetate (10:1) to afford 56 mg (21%) of the title compound as white solids: MS (ESI) m/z 476 [M+H]+, 474 [M−H]−, 1H-NMR (CDCl3) δ 7.88 (2H, d, J=8.5 Hz), 7.61-7.19 (11H, m), 4.31 (2H, t, J=6.6 Hz), 2.92 (2H, t, J=6.6 Hz), 2.49 (3H, s), 2.42 (3H, s).

후처리

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

출처 및 근거

ORD 기록
ord-fcbaa978d9b44a4a864d71193b8f3553
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07001917B2

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