| Identification | More | [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]
767340-03-4 | [Synonyms]
（2Z）-2-amine-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 (2-4)
(2Z)-3-Amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-α]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-2-buten-1-one
(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
(2Z)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]
(2Z)-3-Amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-2-buten-1-one
(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
(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 | [EINECS(EC#)]
616-378-0 | [Molecular Formula]
C16H13F6N5O | [MDL Number]
MFCD12031551 | [Molecular Weight]
405.3 | [MOL File]
767340-03-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 | [Usage]
Sitagliptin intermediate. A dipeptidyl peptidase-4 inhibitor and an anti-hypertensive agent for the treatment of diabetes and hypertension. | [Major Application]
pharmaceutical small molecule | [InChIKey]
RLSFDUAUKXKPCZ-UITAMQMPSA-N | [SMILES]
FC(F)(F)c1[n]2c(nn1)CN(CC2)C(=O)\C=C(/N)\Cc3c(cc(c(c3)F)F)F | [CAS DataBase Reference]
767340-03-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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 |
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