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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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2-Pyrazinecarboxylic acid → 2,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13339
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HRID 13339 반응식
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](O)=O.Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1.[F:28][C:29]([F:64])([F:63])[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[C:37]1[C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=2)=[CH:50][C:40]2[N:41]=C(C3C=CC=CN=3)[NH:43][C:39]=2[CH:38]=1)=[O:31]>C(OCC)(=O)C>[F:64][C:29]([F:28])([F:63])[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[C:37]1[C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=2)=[CH:50][C:40]2[N:41]=[C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)[NH:43][C:39]=2[CH:38]=1)=[O:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10472-Pyrazinecarboxylic acidHCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231457212,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

생성물 1

HCID 231455992,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

14.5 mg of pyrazine-2-carboxylic acid and 27.0 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added in order to a pyridine (1 ml) solution of 53 mg of 1-(2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone obtained in Example 162 (step 6), and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was diluted with saturated saline, and extracted with ethyl acetate. The organic layers were combined, washed with aqueous saturated ammonium chloride and aqueous saturated sodium bicarbonate in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was dissolved in 1 ml of toluene. 9.9 mg of p-toluenesulfonic acid monohydrate was added to it, and the reaction liquid was stirred at 120° C. for 6 hours. After cooled, the reaction liquid was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as an oily substance.

후처리

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. additionwas diluted with saturated saline
  4. extractionextracted with ethyl acetate
  5. washwashed with aqueous saturated ammonium chloride and aqueous saturated sodium bicarbonate in order
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. dissolutionthe resulting residue was dissolved in 1 ml of toluene
  9. addition9.9 mg of p-toluenesulfonic acid monohydrate was added to it
  10. customthe reaction liquid
  11. stirringwas stirred at 120° C. for 6 hours
  12. temperatureAfter cooled
  13. customthe reaction liquid
  14. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  15. dry with materialdried with anhydrous magnesium sulfate
  16. customThe solvent was evaporated away under reduced pressure
  17. customthe residue was purified
  18. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)
  19. customto obtain the entitled compound as an oily substance

출처 및 근거

ORD 기록
ord-e2d067810a9a4f659b1ee89b1ee9e2ba
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728025B2

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