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4-(Trifluoromethyl)benzenesulfonyl chloride → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-4-(trifluoromethyl)benzenesulfonamide

HRID 1368609
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인쇄 미리보기

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HRID 1368609 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:15][C:16]1[N:20]([CH3:21])[N:19]=[C:18]([O:22][CH3:23])[C:17]=1[C:24]1[CH:32]=[CH:31][C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([C:17]3[C:18]([O:22][CH3:23])=[N:19][N:20]([CH3:21])[C:16]=3[NH:15][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])=[CH:25][C:26]=2[O:30][CH2:29]1
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참가 물질

5

반응물 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 222819435-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole

생성물 1

HCID 22281890N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-4-(trifluoromethyl)benzenesulfonamide수율 0.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049
Pyridine
용매
2회

실험 절차

To a solution of 4-dimethylaminopyridine in anhydrous pyridine at 0° C. under an atmosphere of nitrogen was added 4-(trifluoromethyl)benzenesulfonyl chloride (148 mg) in pyridine (1.5 ml). After 10 min the reaction was treated with 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole (Preparation 43) (100 mg) and the reaction was allowed to warm to room temperature and stirred for 12 h. The reaction was concentrated under reduced pressure, the residue treated with 1.0M aqueous citric acid (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins, then 30% water in acetonitrile for 13 mins. Phenomenex Magellen™ 150 mm×21.5 mm column, 40° C.) to yield the title compound as an off-white solid (1 mg).

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionthe residue treated with 1.0M aqueous citric acid (100 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins
  8. wait30% water in acetonitrile for 13 mins

출처 및 근거

ORD 기록
ord-669825bc74284336acd50cf7d636ce37
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06573270B1

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