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Cesium carbonate → 5-(2-Fluoro-phenoxy)-2-pyrazin-2-yl-6-(6-cyano-pyridin-3-yloxy)-1H-benzimidazole

HRID 13329
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HRID 13329 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]#[N:9])=N[CH:7]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:39]=[CH:38][CH:37]=[CH:36][C:18]=1[O:19][C:20]1[C:34]([OH:35])=[CH:33][C:23]2[NH:24][C:25]([C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)=[N:26][C:22]=2[CH:21]=1>CN1CCCC1=O>[F:16][C:17]1[CH:39]=[CH:38][CH:37]=[CH:36][C:18]=1[O:19][C:20]1[C:34]([O:35][C:2]2[CH:7]=[CH:10][C:5]([C:8]#[N:9])=[N:4][CH:3]=2)=[CH:33][C:23]2[NH:24][C:25]([C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)=[N:26][C:22]=2[CH:21]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 1356979845-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole

생성물 1

HCID 231451425-(2-Fluoro-phenoxy)-2-pyrazin-2-yl-6-(6-cyano-pyridin-3-yloxy)-1H-benzimidazole

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
90 °C

실험 절차

7.0 mg of 5-bromo-2-cyano-pyrimidine and 15 mg of cesium carbonate were added to an N-methylpyrrolidinone (0.5 ml) solution of 7.0 mg of 5-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole obtained in the step 1, and the reaction liquid was stirred at 90° C. for 15 minutes. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound a colorless solid.

후처리

  1. customobtained in the step 1
  2. customthe reaction liquid
  3. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  4. additionThe resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound a colorless solid

출처 및 근거

ORD 기록
ord-16448ad5041148a9ab574d8ff2b42526
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728025B2

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