Sodium Sulfate → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641464

反応式

HRID 1641464 の反応式
S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:10]=1[C:11]([NH:13][CH:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])=[O:12].[Br:24][C:25]1[CH:29]=[C:28]([C:30](=[O:39])SCC2C=CC=CC=2)[N:27]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=2)[N:26]=1.CC(C)([O-])C.[K+]>O.CS(C)=O>[Br:24][C:25]1[CH:29]=[C:28]([C:30]([NH:8][C:9]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:10]=2[C:11](=[O:12])[NH:13][CH:14]([CH:16]2[CH2:18][CH2:17]2)[CH3:15])=[O:39])[N:27]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=2)[N:26]=1

参加物

7

反応物 4

HCID 24436Sodium SulfateHCID 23665647Potassium tert-butoxideHCID 435330962-amino-5-chloro-N-(1-cyclopropylethyl)benzamideHCID 86639908S-benzyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbothioate

生成物 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide収率 41.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

0.85 g of anhydrous sodium sulfate was added to a mixed solution comprising 0.24 g of 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide, 0.41 g of S-benzyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbothioate and 5 ml of dimethyl sulfoxide at room temperature, followed by stirring for 5 minutes, and 0.14 g of potassium tert-butoxide was added, followed by reaction at room temperature for 1 hour. The reaction liquid was slowly added to water, the mixed liquid was subjected to extraction with ethyl acetate, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 to 7.5/2.5) to obtain 0.22 g of the desired product.

後処理

  1. customat room temperature
  2. customfollowed by reaction at room temperature for 1 hour
  3. customThe reaction liquid
  4. extractionthe mixed liquid was subjected to extraction with ethyl acetate
  5. washthe organic layer was washed with a sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 to 7.5/2.5)

出典と根拠

ORDレコード
ord-36f05a2a6bec4b3fb2a0c9c96e1054e3
出典データセット
uspto-grants-2012_02
特許番号
US08115006B2

関連ノート

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