Potassium Hydroxide → 4-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1368648노트

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HRID 1368648 반응식
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[C:13]([NH2:22])[N:12]([CH3:23])[N:11]=2)=[CH:4][CH:3]=1.[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].[OH-:40].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:22]([S:36]([C:33]2[CH:34]=[CH:35][C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:31][CH:32]=2)(=[O:37])=[O:40])[C:13]2[N:12]([CH3:23])[N:11]=[C:10]([O:9][CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 234003123-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamine

생성물 1

HCID 222818924-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide수율 79.7%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

To 3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamine (Preparation 26) (105mg) in dichloromethane (20ml) at room temperature was added 4-tert-butylbenzenesulfonyl chloride (2 g), tetrabutylammonium hydrogen sulfate (75 mg) and potassium hydroxide (690 mg), the mixture was sonicated for 3 hrs. The reaction was partitioned between 2N aqueous hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, then brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel, eluting with a solvent gradient of pentane:ethyl acetate (39:1 to 4:1), to yield the title compound as a glass (180 mg).

후처리

  1. customthe mixture was sonicated for 3 hrs
  2. customThe reaction was partitioned between 2N aqueous hydrochloric acid and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with a solvent gradient of pentane:ethyl acetate (39:1 to 4:1)

출처 및 근거

ORD 기록
ord-870fd1bf63ef4f04a5e2fd29ed1cb234
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573270B1

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