Reaction #40544

Reaction equation

diethylaminoethylamine

2-(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazin-4-yl)-1H-benzoimidazole-5-carboxylic acid

triethylamine

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

→

2-(3-Oxo-6-pyridin-4-yl-2,3-dihydropyridazin-4-yl)-1H-benzimidazole-5-carboxylic acid (2-diethylaminoethyl)amide

Solvents

dimethylformamide

water

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for a further 30 minutes
2. 2
   workup.STIRRINGthe mixture is stirred at 50° C. for 3 hours
3. 3
   TemperatureAfter cooling
4. 4
   Filtrationthe precipitate is filtered off with suction
5. 5
   workup.STIRRINGstirred with isopropanol at 60° C.
6. 6
   Filtrationfiltered off with suction
7. 7
   Otherdried in vacuo

Procedure

A mixture consisting of 50 mg of 2-(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazin-4-yl)-1H-benzoimidazole-5-carboxylic acid, 0.065 ml of triethylamine and 1.5 ml of dimethylformamide (DMF) is stirred at room temperature for 10 minutes, mixed with 68.4 mg of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (Hatu) and stirred at room temperature for a further 30 minutes. Then 21 mg of diethylaminoethylamine are added, and the mixture is stirred at 50° C. for 3 hours. After cooling, it is diluted with 5 ml of water, and the precipitate is filtered off with suction and stirred with isopropanol at 60° C., filtered off with suction and dried in vacuo.

Source