1-(2-Amino-3,5-dimethylphenyl)ethan-1-one → N-(2-acetyl-4,6-dimethylphenyl)-3-(((4-chloro-3-methyl-5-isoxazolyl)amino)sulfonyl)-2-thiophenecarboxamide

HRID 2303723

反応式

HRID 2303723 の反応式
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[Cl:13][C:14]1[C:15]([CH3:34])=[N:16][O:17][C:18]=1[N:19](COC)[S:20]([C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28](Cl)=[O:29])(=[O:22])=[O:21]>ClCCl>[C:10]([C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[C:7]([CH3:8])[C:2]=1[NH:1][C:28]([C:24]1[S:25][CH:26]=[CH:27][C:23]=1[S:20]([NH:19][C:18]1[O:17][N:16]=[C:15]([CH3:34])[C:14]=1[Cl:13])(=[O:21])=[O:22])=[O:29])(=[O:12])[CH3:11]

参加物

4

反応物 2

HCID 105831361-(2-Amino-3,5-dimethylphenyl)ethan-1-oneHCID 10738841HCID 10738841、化合物

生成物 1

HCID 9934302N-(2-acetyl-4,6-dimethylphenyl)-3-(((4-chloro-3-methyl-5-isoxazolyl)amino)sulfonyl)-2-thiophenecarboxamide収率 43.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2′-amino-3′,5′-dimethylacetophenone (1.9 g, 11.66 mmol) in dichloromethane (20 mL) at room temperature was added N-(4-chloro-3-methyl-5-isoxazolyl)-N-methoxymethyl-3-sulfamoyl-2-thiophenecarbonyl chloride (Example 51) (1 g, 2.86 mmol). The mixture was stirred for 10 h during which much yellow precipitate formed. The reaction was then concentrated and the residue was diluted with ethyl acetate (50 mL) and washed with 1 N HCl (50 mL). The organic layer was concentrated and the residue was dissolved in methanol (30 mL) followed by the addition of concentrated HCl (15 mL). The mixture was then heated under reflux for 2 h before it was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with water (2×200 mL). The organic layer was separated, dried (MgSO4), the solids filtered and the filtrate concentrated. The residue was then purified by reverse phase HPLC to give N-(2-acetyl-4,6-dimethylphenyl)-3-(((4-chloro-3-methyl-5-isoxazolyl)amino)sulfonyl)-2-thiophenecarboxamide (580 mg, 43%).

後処理

  1. customformed
  2. concentrationThe reaction was then concentrated
  3. additionthe residue was diluted with ethyl acetate (50 mL)
  4. washwashed with 1 N HCl (50 mL)
  5. concentrationThe organic layer was concentrated
  6. dissolutionthe residue was dissolved in methanol (30 mL)
  7. additionfollowed by the addition of concentrated HCl (15 mL)
  8. temperatureThe mixture was then heated
  9. temperatureunder reflux for 2 h before it
  10. additiondiluted with ethyl acetate (200 mL)
  11. washwashed with water (2×200 mL)
  12. customThe organic layer was separated
  13. dry with materialdried (MgSO4)
  14. filtrationthe solids filtered
  15. concentrationthe filtrate concentrated
  16. customThe residue was then purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-ca5dd401af0b4e138c7deede1a18ef2a
出典データセット
uspto-grants-2002_08
特許番号
US06432994B1

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