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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 1367878
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1367878
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178522488HCID 178522488, Verbindung

Produkt 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]-amideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9326a3548b804fa3b3947fc6a110c3f5
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07893267B2

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