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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
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HRID 2391590 반응식
[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
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참가 물질

4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a43706a3e0834483bb658d2c1e0fb29d
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273890B2

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