(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine Chemical Properties

Melting point:

178-180°C

Boiling point:

555.1±60.0 °C(Predicted)

Density 

1.60±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.11±0.70(Predicted)

color 

White

CAS DataBase Reference

767340-03-4(CAS DataBase Reference)

(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine Usage And Synthesis

Chemical Properties

White Solid

Uses

Sitagliptin intermediate. A dipeptidyl peptidase-4 inhibitor and an anti-hypertensive agent for the treatment of diabetes and hypertension.

Synthesis

Example 1: Preparation of (Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one. 4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-1-one (427.0 g, prepared according to US 7,326,708 B2 or J. Am. Chem. Soc. 2009) was mixed with methanol (1000 ml) was mixed and passed through dry ammonia (53.6 g) at 25-30°C. The reaction mixture was then heated to reflux (60-65°C) and the reaction was maintained at this temperature for 3.0-4.0 hours. Upon completion of the reaction, the mixture was cooled to 0-5 °C and the precipitated solid was collected by filtration and washed with cold methanol. The wet filter cake was dried at 60-65 °C to afford 340.0 g of the target product (2Z)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine in a molar yield of 79.8% and an HPLC purity of 98.99%.

References

[1] Journal of the American Chemical Society, 2009, vol. 131, # 25, p. 8798 - 8804
[2] Patent: WO2016/110750, 2016, A1. Location in patent: Page/Page column 15; 16
[3] Patent: WO2004/85378, 2004, A1. Location in patent: Page 16
[4] Patent: WO2005/97733, 2005, A1. Location in patent: Page/Page column 23-24
[5] Patent: WO2006/81151, 2006, A1. Location in patent: Page/Page column 14; 15

(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine(767340-03-4)Related Product Information

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