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4-Pyridinecarboxaldehyde → 1-Ethyl-3,3,5-trimethyl-7-{4-[(pyridin-4-ylmethyl)amino]butyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1504128
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1504128
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:31]=[CH:30][C:17]2[N:18]([CH2:28][CH3:29])[C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[C:21](=[O:24])[N:22]([CH3:23])[C:16]=2[CH:15]=1.[BH4-].[Na+]>CO>[CH2:28]([N:18]1[C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[C:21](=[O:24])[N:22]([CH3:23])[C:16]2[CH:15]=[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH:31]=[CH:30][C:17]1=2)[CH3:29]
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Komponenten

5

Edukt 3

HCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 706571287-(4-Aminobutyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Produkt 1

HCID 706567041-Ethyl-3,3,5-trimethyl-7-{4-[(pyridin-4-ylmethyl)amino]butyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

4-Pyridine carbaldehyde(0.15 ml) was added to a methanol solution (10 ml) of 7-(4-aminobutyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione(0.51 g). The mixture was stirred for an hour at room temperature under nitrogen atmosphere. Sodium borohydride (0.2 g) was added to the mixture, and the mixture was stirred at room temperature overnight. The liquid was then condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate: methanol=9:1→3:2). The purified product was condensed under reduced pressure to give the title compound(0.38 g) as a colorless oily matter.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customcondensed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=9:1→3:2)
  4. customcondensed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae3245243788438292ce085e5f3f3b70
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09212187B2

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