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Potassium Carbonate → 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1695488
ノート
印刷プレビュー

反応式

HRID 1695488 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH:13]=O)=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:17][O:18][C:19]([C:21]1[N:22]([CH3:27])[N:23]=[C:24]([NH2:26])[CH:25]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CO.Cl>[CH3:17][O:18][C:19]([C:21]1[N:22]([CH3:27])[N:23]=[C:24]([NH:26][CH2:13][C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][O:10][C:11]=2[CH3:15])[CH:25]=1)=[O:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 167282913-(4-Fluorophenyl)-5-methylisoxazole-4-carboxaldehydeHCID 66643934methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate hydrochloride

生成物 1

HCID 666437125-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester収率 27%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒

実験手順

To a solution of 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carbaldehyde (1.32 g, 6.44 mmol) and the 5-amino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester hydrochloride (1.0 g, 6.44 mmol) in methanol (30 mL) at room temperature was added potassium carbonate (890 mg, 6.44 mmol) and then the reaction mixture was heated under reflux for 2 h. After cooling to room temperature sodium borohydride (487 mg, 12.9 mmol) was added and then the mixture heated under reflux for 12 h. The mixture was then cooled and treated with hydrochloric acid (1 N, 10 drops) and evaporated. Water was then added and the mixture extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid (2 N) and then extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulfate, filtered and evaporated to afford 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (27%) which was obtained as a white solid.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. additionwas added
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 12 h
  6. temperatureThe mixture was then cooled
  7. customevaporated
  8. additionWater was then added
  9. extractionthe mixture extracted with ethyl acetate
  10. extractionextracted with ethyl acetate
  11. dry with materialThe combined organic extracts were then dried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated

出典と根拠

ORDレコード
ord-ec0337d3de284c189b7a8d8d00f939c6
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163728B2

反応ノート

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