Methanol → HCID 58763666, Verbindung

HRID 858943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858943
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:5].CO.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][N:25]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Br:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][NH:1][C:2]2[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=2[C:4]([NH:6][C:7]2[N:8]=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:5])=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 601321962-Amino-N-(isoquinolin-3-yl)benzamide

Produkt 1

HCID 58763666HCID 58763666, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

3.46 g (13.17 mmol) of 2-amino-N-isoquinolin-3-yl-benzamide is introduced into 50 ml of methanol, mixed with 1.5 ml of glacial acetic acid as well as 2.45 g (13.17 mmol) of 2-bromopyridine-5-carbaldehyde and stirred for 24 hours under argon and in a moisture-free environment at room temperature. Then, it is mixed with 828 mg (13.17 mmol) of sodium cyanoborohydride and stirred for another 24 hours at room temperature. After concentration by evaporation under vacuum, the residue is taken up in dilute sodium bicarbonate solution and suctioned off. The residue that is obtained is absorptively precipitated in a little ethyl acetate and suctioned off repeatedly. The residue that is obtained in this case is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 3.27 g (57% of theory) of 2-[(6-bromo-pyridin-3-ylmethyl)-amino]-N-isoquinolin-3-yl-benzamide is obtained.

Aufarbeitung

  1. stirringstirred for another 24 hours at room temperature
  2. concentrationAfter concentration
  3. customby evaporation under vacuum
  4. customThe residue that is obtained
  5. customis absorptively precipitated in a little ethyl acetate
  6. customThe residue that is obtained in this case
  7. customis chromatographed on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d7824f688092410399edd3f437b20662
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148357B2

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