Reaktion #156148

Reaktionsgleichung

Sodium triacetoxyborohydride

1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde

acetic acid

N-(4-methylthiazol-5-ylmethyl)-N-(2-pyridin-3-ylethyl)amine

→

title compound

Ausbeute 48.8%

1-ethyl-3,3,5-trimethyl-7-{[N-(4-methylthiazol-5-ylmethyl)-N-(2-pyridin-3-ylethyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Ausbeute 48.8%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   SonstigeThe reaction liquid
3. 3
   Sonstigecondensed under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→50:50)
5. 5
   Sonstigecondensed under reduced pressure
6. 6
   WaschenThe residue was washed with diethyl ether
7. 7
   Sonstigedried

Vorschrift

1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde (0.423 g) and acetic acid (0.14 g) were added to a 1,2-dichloroethane solution (10 ml) of N-(4-methylthiazol-5-ylmethyl)-N-(2-pyridin-3-ylethyl)amine (0.36 g). The mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (0.48 g) was added, and the mixture was stirred at room temperature overnight. The reaction liquid was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→50:50). The purified product was condensed under reduced pressure. The residue was washed with diethyl ether, and dried to give the title compound (0.37 g) as a white powder.

Quelle