(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
- Product Name
- (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
- CAS No.
- 767340-03-4
- Chemical Name
- (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
- Synonyms
- 7(8H)-;Sitagliptin-12;Sitagliptin Enamine;Sitagliptin Impurity 9;Sitagliptin Enamine Imp;3-a]pyrazine-7(8H)-yl]-1-(2;(Z)-3-amino-1-(3-(trifluoromethyl);5-trifluorophenyl)but-2-en-2-amine;(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5;(2Z)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]
- CBNumber
- CB31564663
- Molecular Formula
- C16H13F6N5O
- Formula Weight
- 405.3
- MOL File
- 767340-03-4.mol
(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 Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- O865000
- Product name
- (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine
- Packaging
- 50mg
- Price
- $990
- Updated
- 2021/12/16
- Product number
- 12843
- Product name
- (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine
- Packaging
- 25mg
- Price
- $2000
- Updated
- 2021/12/16
- Product number
- X4795
- Product name
- (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
- Packaging
- 100g
- Price
- $393
- Updated
- 2021/12/16
- Product number
- 091141
- Product name
- (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
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $435
- Updated
- 2021/12/16
- Product number
- 12843
- Product name
- (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine
- Packaging
- 5mg
- Price
- $875
- Updated
- 2021/12/16
(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,Usage,Production
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
764667-65-4
767340-03-4
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 Preparation Products And Raw materials
Raw materials
Preparation Products
(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 Suppliers
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View Lastest Price from (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 manufacturers
- Product
- Sitagliptin Impurity 14 767340-03-4
- Price
- US $0.00-0.00/mg
- Min. Order
- 5mg
- Purity
- 95%+
- Supply Ability
- 1000mg
- Release date
- 2025-02-17
- 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 767340-03-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-03-27
- 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 767340-03-4
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2018-07-28