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Ammonia → 5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxamide

HRID 2391590
ノート
印刷プレビュー

反応式

HRID 2391590 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([C:12]3[S:16][C:15]([C:17]([O:19]C)=O)=[C:14]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:13]=3)[CH:10]=[N:11][C:6]2=[CH:5][CH:4]=1.[NH3:33]>CO>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([C:12]3[S:16][C:15]([C:17]([NH2:33])=[O:19])=[C:14]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:13]=3)[CH:10]=[N:11][C:6]2=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 222AmmoniaHCID 68767171methyl 5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

生成物 1

HCID 251534915-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
130 °C

実験手順

A mixture of 0.74 g of methyl 5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B7b) and 200 ml of a saturated solution of ammonia in methanol was stirred in an autoclave at 130° C. for 10 h. The reaction mixture was allowed to cool down to room temperature and concentrated to about half of the volume. The precipitated solid was filtered, dissolved in 4 ml methanol/DMSO (1:1) and purified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v)). After lyophilization the obtained solid was crystallized with dichloromethane/n-hexane to give the title compound.

後処理

  1. temperatureto cool down to room temperature
  2. concentrationconcentrated to about half of the volume
  3. filtrationThe precipitated solid was filtered
  4. dissolutiondissolved in 4 ml methanol/DMSO (1:1)
  5. custompurified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v))
  6. customAfter lyophilization the obtained solid was crystallized with dichloromethane/n-hexane

出典と根拠

ORDレコード
ord-a43706a3e0834483bb658d2c1e0fb29d
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273890B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート