(5-(4-chlorophenyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)(4-(3-(trifluoroMethyl)phenyl)piperazin-1-yl)Methanone Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

InChI

InChI=1S/C23H18ClF3N6O/c24-17-6-4-15(5-7-17)19-8-9-20-21(28-19)33(30-29-20)22(34)32-12-10-31(11-13-32)18-3-1-2-16(14-18)23(25,26)27/h1-9,14H,10-13H2

InChIKey

GQZISVAEKVEVFV-UHFFFAOYSA-N

SMILES

C(N1C2=NC(C3=CC=C(Cl)C=C3)=CC=C2N=N1)(N1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)=O

(5-(4-chlorophenyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)(4-(3-(trifluoroMethyl)phenyl)piperazin-1-yl)Methanone Usage And Synthesis

Uses

(5-(4-chlorophenyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)(4-(3-(trifluoroMethyl)phenyl)piperazin-1-yl)Methanone is mainly used in pharmaceutical synthesis and scientific research.

Synthesis

1.4. Synthesis of [5-(4-chlorophenyl)[1,2,3]triazolo[4,5-b]pyridin-3-yl][4-(3-trifluoromethylphenyl)piperazin-1-yl]methanone In a 100-mL three-necked flask, 0.55 g (1.17 mmol) of 4-(3-trifluoromethylphenyl)piperazine-1-carboxylic acid [3-amino-6-(4-chlorophenyl)pyridin-2-yl]amide obtained in step 1.3 was dissolved in a mixture of 5 mL of water and 5 mL of 37% aqueous hydrochloric acid solution and cooled in an ice bath. 0.24 g (3.50 mmol) of sodium nitrite solution dissolved in 4 mL of water was slowly added dropwise through a dropping funnel. The reaction mixture was stirred at 0°C for 2 hours. Subsequently, the mixture was allowed to stand in an ice bath for 1 h. The solid product was collected by filtration. The solid was washed with 3 x 10 mL of water to give a beige solid. The solid was vacuum dried in the presence of phosphorus pentoxide. The product was purified by silica gel column chromatography using sequentially 80:20 and 60:40 cyclohexane and ethyl acetate mixture as eluent. The collected oil was crystallized with pentane to give 0.15 g (yield: 26%) of the target compound in the form of a light yellow powder. Melting point: 139-141°C. LC-MS (m/z): 487 (MH+). IR (KBr, cm-1): 1718, 1591. 1H NMR (DMSO-d6, δ ppm): 8.80 (d, 1H), 8.25 (dd, 3H), 7.60 (d, 2H), 7.45 (t, 1H), 7.25 (d, 1H), 7.20 (s, 1H), 7.10 (d, 1H), 3.30-4.00 (m, 8H).

References

[1] Patent: US2010/41670, 2010, A1. Location in patent: Page/Page column 4