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Ethyl Acetate → N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide

HRID 40709
ノート
印刷プレビュー

反応式

HRID 40709 の反応式
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH:22]=[CH:23]N(C)C)=[CH:17][C:16]=1[N:28]([CH3:32])[C:29](=[O:31])[CH3:30].C(OCC)(=O)C>C(O)(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:6]3[N:5]=[CH:4][C:3]([C:7]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[O:8])=[C:2]3[N:1]=[CH:23][CH:22]=2)=[CH:17][C:16]=1[N:28]([CH3:32])[C:29](=[O:31])[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 11550150(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanoneHCID 67279027N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-acetamide

生成物 1

HCID 15604196N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide収率 79%

試薬・触媒・溶媒 1

HCID 176Acetic Acid
溶媒

実験手順

A mixture of 0.083 g (0.43 mmol) of (5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone and 0.12 g (0.43 mmol) of N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-acetamide in 12 ml of glacial acetic acid was refluxed for 1.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 139 mg of N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 79%).

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution
  4. customThe two layers were separated
  5. washthe aqueous layer was washed with 10 ml of dichloromethane
  6. washThe organic layers were washed with 10 ml of water
  7. dry with materialdried over magnesium sulfate
  8. customThe dichloromethane layer was evaporated to dryness
  9. customto yield an oil which

出典と根拠

ORDレコード
ord-e17596a528fc4e2cab341c6cc734ccc3
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08530482B2

反応ノート

読み込み中…

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