Reaktion #461283

Reaktionsgleichung

sodium hydroxide

6-acetylamino-1-(3-methylbenzyl)-4-methyl-hexahydro-1H-1,4-diazepine

1H-indazole-3-carboxylic acid

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

Ausbeute 32.4%

N-[1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide

Ausbeute 32.4%

Lösungsmittel

hydrochloric acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionextracted with chloroform
3. 3
   WaschenThe organic layer is washed with water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   SonstigeThe solvent is evaporated under reduced pressure
6. 6
   Sonstigeto give an oil
7. 7
   workup.STIRRINGis stirred at 25° C. for 2 hours
8. 8
   WaschenThe reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution
9. 9
   Trocknendried over magnesium sulfate
10. 10
    Sonstigeevaporated under reduced pressure
11. 11
    SonstigeThe residue is chromatographed on silica gel with elution of acetone
12. 12
    workup.ADDITIONFractions containing the title compound
13. 13
    Sonstigeevaporated under reduced pressure

Vorschrift

A solution of 6-acetylamino-1-(3-methylbenzyl)-4-methyl-hexahydro-1H-1,4-diazepine (0.9 g) in 10% hydrochloric acid (20 ml) is refluxed with stirring for 2 hours. After cooling, the reaction mixture is basified with 48% aqueous sodium hydroxide solution and extracted with chloroform. The organic layer is washed with water and dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give an oil. A mixture of this oil, 1H-indazole-3-carboxylic acid (530 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (630 mg) and dichloromethane (20 ml) is stirred at 25° C. for 2 hours. The reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is chromatographed on silica gel with elution of acetone. Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (0.4 g) as an oil.

Quelle