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2-Pyrazinecarboxylic acid → N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazine-2-carboxamide

HRID 408260
ノート
印刷プレビュー

反応式

HRID 408260 の反応式
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]2[NH:12][CH:13]=[C:14]([NH2:15])[C:3]=12.[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[C:22](O)=[O:23].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.[Li+].[OH-]>C(Cl)Cl.O>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=[C:4]2[NH:12][CH:13]=[C:14]([NH:15][C:22]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][N:16]=3)=[O:23])[C:3]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10472-Pyrazinecarboxylic acidHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602053084-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine

生成物 1

HCID 60205416N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazine-2-carboxamide
収率 79.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

4-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.200 g, 0.849 mmol, Example 11, Step G) and pyrazine-2-carboxylic acid (0.221 g, 1.78 mmol) were placed in DCM (5 mL) at room temperature. BOP-Cl (0.454 g, 1.78 mmol) was then added, followed by the addition of triethylamine (0.592 mL, 4.24 mmol). The reaction was stirred for 1 hour. 3M aqueous LiOH (3 mL) was then added, and the reaction was stirred for 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the reaction was filtered. The resulting solid was slurried with 10:1 DCM:MeOH and filtered to give solid N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazine-2-carboxamide (0.23 g, 79% yield).

後処理

  1. stirringthe reaction was stirred for 10 minutes
  2. filtrationthe reaction was filtered
  3. filtrationMeOH and filtered

出典と根拠

ORDレコード
ord-5dda7ff40d134954a15f83d2b6a8e695
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08758830B2

反応ノート

読み込み中…

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