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

반응식

HRID 13298 반응식
[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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-01fe6a63373040538f17b6bccf20103d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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