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Ethyl Acetate → 3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

HRID 872990
ノート
印刷プレビュー

反応式

HRID 872990 の反応式
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13](=[O:25])[N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([CH3:18])[C:16]=1[CH3:17])=[O:11].CC([O-])(C)C.[K+].[Cl:32][C:33]1[C:34]([C:40]([NH2:42])=[O:41])=[N:35][CH:36]=[CH:37][C:38]=1Cl.CCOC(C)=O>CN(C=O)C.O>[Cl:32][C:33]1[C:34]([C:40]([NH2:42])=[O:41])=[N:35][CH:36]=[CH:37][C:38]=1[O:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10]([C:12]2[C:13](=[O:25])[N:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:15]([CH3:18])[C:16]=2[CH3:17])=[O:11])=[C:2]([F:1])[CH:7]=1
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 8857Ethyl AcetateHCID 231651433,4-Dichloropyridine-2-carboxamideHCID 23665647Potassium tert-butoxideHCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

生成物 1

HCID 730510753-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.879 mmol) and t-BuOK (118 mg, 1.05 mmol) in DMF (3 mL) was stirred at rt for 30 minutes, then 3,4-dichloropicolinamide (201 mg, 1.05 mmol) was added. The reaction mixture was heated to 120° C. and stirred for 12 hours. EtOAc (1 mL) and H2O (20 mL) were added, and the resulted mixture was stirred at rt overnight. Filtered to give the title compound as a brown solid (379 mg, 87.0%).

後処理

  1. temperatureThe reaction mixture was heated to 120° C.
  2. stirringstirred for 12 hours
  3. stirringthe resulted mixture was stirred at rt overnight
  4. filtrationFiltered

出典と根拠

ORDレコード
ord-8ff577587b95405dbbb1e89f95d4e603
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975282B2

反応ノート

読み込み中…

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