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2-Pyrazinecarboxylic acid → 5-(2-Cyano-phenoxy)-2-pyrazin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13295
ノート
印刷プレビュー

反応式

HRID 13295 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](O)=O.OC1C2N=NNC=2C=CC=1.[H-].CN(C)CCCN=C=NCC.[C:32]([C:34]1[CH:59]=[CH:58][CH:57]=[CH:56][C:35]=1[O:36][C:37]1[CH:38]=[C:39]([NH2:55])[C:40]([NH2:54])=[CH:41][C:42]=1[O:43][C:44]1[CH:45]=[N:46][C:47]([S:50]([CH3:53])(=[O:52])=[O:51])=[CH:48][CH:49]=1)#[N:33]>C(OCC)(=O)C.CN(C)C=O>[C:32]([C:34]1[CH:59]=[CH:58][CH:57]=[CH:56][C:35]=1[O:36][C:37]1[C:42]([O:43][C:44]2[CH:45]=[N:46][C:47]([S:50]([CH3:53])(=[O:51])=[O:52])=[CH:48][CH:49]=2)=[CH:41][C:40]2[NH:54][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[N:55][C:39]=2[CH:38]=1)#[N:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10472-Pyrazinecarboxylic acidHCID 231453124-(2-Cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamineHCID 866192011-(3-Dimethylaminopropyl)-3-ethylcarbodiimide monohydrideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 231452075-(2-Cyano-phenoxy)-2-pyrazin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

21 mg of pyrazine-2-carboxylic acid, 52 mg of hydroxybenzotriazole and 52 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydride were added to a dimethylformamide (2 ml) solution of 72 mg of 4-(2-cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in Example 196 (step 5), and the reaction liquid was stirred at room temperature for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was dissolved in 1 ml of N-methylpyrrolidinone, and 20 mg of ytterbium trifluoromethanesulfonate was added to it, and the reaction liquid was stirred at 160° C. for 2 h ours. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=30/1) and through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a brown solid.

後処理

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with aqueous saturated sodium bicarbonate, water and saturated saline in order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. dissolutionthe resulting residue was dissolved in 1 ml of N-methylpyrrolidinone
  7. addition20 mg of ytterbium trifluoromethanesulfonate was added to it
  8. customthe reaction liquid
  9. stirringwas stirred at 160° C. for 2 h ours
  10. customThe reaction liquid
  11. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  12. dry with materialdried with anhydrous sodium sulfate
  13. customThe solvent was evaporated away under reduced pressure
  14. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=30/1)
  15. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-b0457459d64b4664b6ce4025aaac386e
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728025B2

反応ノート

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