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Triethylamine → N-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-I H-pyrazol-1-yl]ethyl}-1-methyl-1H-imidazole-4-sulfonamide

HRID 353078
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HRID 353078 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].[CH3:22][N:23]1[CH:27]=[C:26]([S:28](Cl)(=[O:30])=[O:29])[N:25]=[CH:24]1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][S:28]([C:26]2[N:25]=[CH:24][N:23]([CH3:22])[CH:27]=2)(=[O:30])=[O:29])[C:10]=1[CH2:11][CH3:12]
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반응물 3

HCID 8471TriethylamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

생성물 1

HCID 10183664N-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-I H-pyrazol-1-yl]ethyl}-1-methyl-1H-imidazole-4-sulfonamide수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

A solution of the amine of Example 43 (98 mg, 0.30 mmol) in dimethylformamide (3.75 ml) was treated with 1-methylimidazole-4-sulphonyl chloride (60 mg, 0.33 mmol) and triethylamine (46 μL, 0.33 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic extract was dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (55 mg) as a white solid, m.p. 172-174° C.

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

출처 및 근거

ORD 기록
ord-4c89d6dabf5f4b568460f9241d3ee33b
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06750230B2

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