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Pyridine → isoquinoline-3-carboxylic acid [4-(5-benzoyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide

HRID 1910149
ノート
印刷プレビュー

反応式

HRID 1910149 の反応式
[N:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[S:3][C:2]=1[NH:10][C:11]([C:13]1[C:18]2[NH:19][C:20]([NH:22][C:23]([C:25]3[N:26]=[CH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:24])=[N:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)=[O:12].N1C=CC=CC=1.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl.C(OCC)(=O)C>[C:41]([N:6]1[CH2:7][CH2:8][C:9]2[N:1]=[C:2]([NH:10][C:11]([C:13]3[C:18]4[N:19]=[C:20]([NH:22][C:23]([C:25]5[N:26]=[CH:27][C:28]6[C:33]([CH:34]=5)=[CH:32][CH:31]=[CH:30][CH:29]=6)=[O:24])[NH:21][C:17]=4[CH:16]=[CH:15][CH:14]=3)=[O:12])[S:3][C:4]=2[CH2:5]1)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178522488HCID 178522488、化合物

生成物 1

HCID 58026653isoquinoline-3-carboxylic acid [4-(5-benzoyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide収率 47%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

To a solution of 30 mg (0.063 mmol) of isoquinoline-3-carboxylic acid [7-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide (Example 198) in DCM (2 mL) was added pyridine (0.5 mL) and benzoyl chloride (0.05 mL). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (20 mL), the organic phase was washed with sat. aq. Na2CO3 solution, dried over Na2SO4, and concentrated under reduced pressure. The crude product was dissolved in DCM (0.5 mL), hexane was added (4 mL), and the resulting precipitate was filtered and dried to provide 17 mg (47%) of isoquinoline-3-carboxylic acid [4-(5-benzoyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 574 (M+1)+.

後処理

  1. washthe organic phase was washed with sat. aq. Na2CO3 solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude product was dissolved in DCM (0.5 mL)
  5. additionhexane was added (4 mL)
  6. filtrationthe resulting precipitate was filtered
  7. customdried

出典と根拠

ORDレコード
ord-03a0f66c448d42da81dc08f903a1f733
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598353B2

反応ノート

読み込み中…

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