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 1062790ノート

反応式

HRID 1062790 の反応式
[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]

参加物

6

反応物 3

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

生成物 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]benzenesulfonamide収率 79.7%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To 3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamine (Preparation 26) (105 mg) in dichloromethane (20 ml) 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).

後処理

  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)

出典と根拠

ORDレコード
ord-be3d082eeadb49b7b9ec43c4e1f61ada
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

反応ノート

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