Reaktion #461284

Reaktionsgleichung

6-Amino-1-(2,5-dimethylbenzyl)-4-methylhexahydro-1H-1,4-diazepine

1H-indazole-3-carboxylic acid

→

title compound

Ausbeute 67.4%

N-[1-(2,5-dimethylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide

Ausbeute 67.4%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is heated at 60° C. for 2 hours
2. 2
   SonstigeThe solvent is evaporated under reduced pressure
3. 3
   workup.ADDITIONthe residue is diluted with water
4. 4
   Extraktionextracted with chloroform
5. 5
   WaschenThe organic layer is washed successively with water and aqueous sodium hydroxide solution
6. 6
   Trocknendried over sodium sulfate
7. 7
   SonstigeThe solvent is evaporated under reduced pressure
8. 8
   Sonstigethe residue is chromatographed on silica gel with elution of acetone
9. 9
   workup.ADDITIONFractions containing the title compound
10. 10
    Sonstigeevaporated under reduced pressure

Vorschrift

To a solution of 1H-indazole-3-carboxylic acid (1.0 g) in N,N-dimethylformamide (20 ml), N,N'-carbonyldiimidazole (1.1 g) is added, and the mixture is heated at 60° C. for 2 hours. 6-Amino-1-(2,5-dimethylbenzyl)-4-methylhexahydro-1H-1,4-diazepine (1.5 g) is added to the reaction mixture, and the mixture is heated at 60° C. for 2 hours. The solvent is evaporated under reduced pressure, and the residue is diluted with water and extracted with chloroform. The organic layer is washed successively with water and aqueous sodium hydroxide solution, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and 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 (1.6 g) as an oil. The free base thus obtained is converted to the fumarate of the title compound in a usual manner, m.p. 168°-170° C. (recrystallized from ethanol).

Quelle