Potassium Carbonate → 1-(2-(6-(4-fluoro-phenylsulfanyl)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13357

반응식

HRID 13357 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]1[C:28](F)=[CH:27][C:26]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=O)=[C:25]([N+:39]([O-])=O)[CH:24]=1)(=[O:17])[CH3:16].O.O.[Sn](Cl)Cl>C(=O)(O)[O-].[Na+].CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:28]2[C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:15](=[O:17])[CH3:16])=[CH:24][C:25]3[NH:39][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:30][C:26]=3[CH:27]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 677894-FluorothiophenolHCID 23145313Pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide

생성물 1

HCID 231455871-(2-(6-(4-fluoro-phenylsulfanyl)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
100 °C

실험 절차

20 mg of 4-fluoro-benzenethiol and 30 mg of potassium carbonate were added in order to an N,N-dimethylformamide (1 ml) solution of 50 mg of pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide, and the reaction liquid was stirred at 100° C. for 2 hours. 30 mg of tin(II) chloride dihydrate was added to the reaction liquid, and the reaction liquid was stirred at 100° C. for 3 hours. After cooled, the reaction liquid was diluted with aqueous saturated sodium bicarbonate and extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

후처리

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at 100° C. for 3 hours
  4. temperatureAfter cooled
  5. customthe reaction liquid
  6. extractionextracted with chloroform
  7. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. customThe resulting residue was purified
  10. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

출처 및 근거

ORD 기록
ord-193abfcda9f243b19d8caf7097c67caa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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