Cesium carbonate → HCID 23145656, 화합물

HRID 13374

반응식

HRID 13374 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:17]1[C:18]([O:35][C:36]2[CH:37]=[N:38][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][CH:41]=2)=[CH:19][C:20]([N+:32]([O-])=O)=[C:21]([NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=O)[CH:22]=1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][C:17]1[C:18]([O:35][C:36]2[CH:37]=[N:38][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][CH:41]=2)=[CH:19][C:20]2[NH:32][C:24]([C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)=[N:23][C:21]=2[CH:22]=1

참가 물질

8

반응물 5

HCID 10796Cesium carbonateHCID 61436Stannous chloride dihydrateHCID 949522,5-DifluorophenolHCID 516892Sodium BicarbonateHCID 86619212Pyrazine-2-carboxylic acid (5-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenyl)-amide

생성물 1

HCID 23145656HCID 23145656, 화합물

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
90 °C

실험 절차

15 mg of 2,5-difluoro-phenol and 28 mg of cesium carbonate were added to an N-methylpyrrolidinone (0.5 ml) solution of 26 mg of pyrazine-2-carboxylic acid (5-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenyl)-amide obtained in (step 1), and the reaction liquid was stirred at 90° C. for 15 minutes, and 100 mg of tin(II) chloride dihydrate was added to the reaction liquid. The reaction liquid was stirred at 90° C. for 1 hour, and ethyl acetate and aqueous saturated sodium bicarbonate were added to it. The deposit was removed through filtration, the solvent was evaporated away under reduced pressure, and the residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of 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 as a pale yellow solid.

후처리

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. stirringwas stirred at 90° C. for 1 hour
  5. customThe deposit was removed through filtration
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  8. additionThe solvent of the resulting fraction was diluted with ethyl acetate
  9. washwashed with aqueous saturated sodium bicarbonate
  10. dry with materialdried with anhydrous sodium sulfate
  11. customThe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-8ebde3e6dcdb4147af6b0162605e6e43
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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