1-methyl-1H-pyrazole-3-carboxylic acid → 5-(2-Fluoro-phenoxy)-2-(1-methyl-1H-pyrazol-3-yl)-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13298

Reaktionsgleichung

Reaktionsgleichung von HRID 13298
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7](O)=O)=[N:3]1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[F:32][C:33]1[CH:58]=[CH:57][CH:56]=[CH:55][C:34]=1[O:35][C:36]1[CH:37]=[C:38]([NH2:54])[C:39]([NH2:53])=[CH:40][C:41]=1[O:42][C:43]1[CH:44]=[N:45][C:46]([S:49]([CH3:52])(=[O:51])=[O:50])=[CH:47][CH:48]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C)C=O>[F:32][C:33]1[CH:58]=[CH:57][CH:56]=[CH:55][C:34]=1[O:35][C:36]1[C:41]([O:42][C:43]2[CH:44]=[N:45][C:46]([S:49]([CH3:52])(=[O:50])=[O:51])=[CH:47][CH:48]=2)=[CH:40][C:39]2[NH:53][C:7]([C:4]3[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=3)=[N:54][C:38]=2[CH:37]=1

Komponenten

8

Edukt 4

HCID 5731761-methyl-1H-pyrazole-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231451984-(2-Fluoro-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamineHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 1356979925-(2-Fluoro-phenoxy)-2-(1-methyl-1H-pyrazol-3-yl)-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4.3 mg of 1-methyl-1H-pyrazole-3-carboxylic acid, 6.0 mg of hydroxybenzotriazole and 8.5 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added to a dimethylformamide (0.5 ml) solution of 15 mg of 4-(2-fluoro-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in Example 200, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with chloroform, washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 3 mg of p-toluenesulfonic acid was added to the resulting residue, and the reaction liquid was stirred at 120° C. for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1) to obtain the entitled compound as a white solid.

Aufarbeitung

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure, and 3 mg of p-toluenesulfonic acid
  6. additionwas added to the resulting residue
  7. customthe reaction liquid
  8. stirringwas stirred at 120° C. for 2 hours
  9. customThe reaction liquid
  10. washwashed with water
  11. dry with materialdried with anhydrous sodium sulfate
  12. customThe solvent was evaporated away under reduced pressure
  13. customthe resulting residue was purified
  14. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-01fe6a63373040538f17b6bccf20103d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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