Réaction #172040

Équation de réaction

LiOH

3-(2H-1,2,3-triazol-2-yl)aniline

DIPEA

ethyl 5-cyano-2,6-dichloronicotinate

THF

→

3-(2H-1,2,3-triazol-2-yl)phenylamino-6-chloro-5-cyanonicotinic acid

Solvants

water

water

ACN

Conditions de réaction

Traitement

1. 1
   Filtrationthe resulting precipitate was collected by filtration
2. 2
   Autreto give intermediate, which
3. 3
   workup.STIRRINGAfter stirring at ambient temperature for 2 h
4. 4
   AutreTHF was removed by concentration
5. 5
   Filtrationthe resulting precipitate was collected by filtration

Mode opératoire

To a suspension of ethyl 5-cyano-2,6-dichloronicotinate Q4 (1.10 g, 4.4 mmol) in ACN (20 ml) was added 3-(2H-1,2,3-triazol-2-yl)aniline Q5 (774 mg, 4.84 mmol) and DIPEA (1.18 mL, 6.6 mmol). The mixture was stirred at ambient temperature for 15 h, and diluted with water; the resulting precipitate was collected by filtration to give intermediate, which was added THF (12 mL) and a solution of LiOH (106 mg, 8.8 mmol) in water (6 mL). After stirring at ambient temperature for 2 h, THF was removed by concentration and the residue was acidified to pH 2, the resulting precipitate was collected by filtration to give 2-(3-(2H-1,2,3-triazol-2-yl)phenylamino-6-chloro-5-cyanonicotinic acid Q6 (870 mg).

Source