Methanol → HCID 58763666, Verbindung

HRID 2110176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110176
[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-e65fa540b54e40b79ea9333191492a7f
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517894B2

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