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764667-65-4

764667-65-4 Structure

764667-65-4 Structure
IdentificationMore
[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)butan-2-one
[CAS]

764667-65-4
[Synonyms]

4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one
1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1,3-butanedione
1-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-α]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1,3-butanedione
4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one
(2Z)-1-[3-(Trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(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)butan-2-one
[EINECS(EC#)]

619-997-4
[Molecular Formula]

C16H12F6N4O2
[MDL Number]

MFCD11111443
[Molecular Weight]

406.28
[MOL File]

764667-65-4.mol
Chemical PropertiesBack Directory
[Appearance]

Brown Oil
[Melting point ]

82-84°C
[Boiling point ]

513.9±60.0 °C(Predicted)
[density ]

1.60±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

11.44±0.20(Predicted)
[color ]

Off-White to Pale Beige
[Usage]

Sitagliptin intermediate
[Major Application]

pharmaceutical small molecule
[InChI]

1S/C16H12F6N4O2/c17-10-6-12(19)11(18)4-8(10)3-9(27)5-14(28)25-1-2-26-13(7-25)23-24-15(26)16(20,21)22/h4,6H,1-3,5,7H2
[InChIKey]

QAEDTLFWHIEVPK-UHFFFAOYSA-N
[SMILES]

FC(F)(F)c1[n]2c(nn1)CN(CC2)C(=O)CC(=O)Cc3c(cc(c(c3)F)F)F
[LogP]

2.424
[CAS DataBase Reference]

764667-65-4(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

WGK 3
[REACH Registrations]

Active
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

Brown Oil
[Uses]

4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one is a Sitagliptin intermediate.
[Uses]

Sitagliptin intermediate
[Synthesis]

ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

1151240-88-8

3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

486460-21-3

(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)butan-2-one

764667-65-4

Potassium tert-butoxide (2.24 g, 20 mmol) was dissolved in 40 mL of tetrahydrofuran in a 100 mL single-necked flask and stirred for 1 min at room temperature. Subsequently, ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate (1.91 g, 10 mmol) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (2.60 g, 10 mmol) were added sequentially and stirring was continued for 60 min at room temperature. After completion of the reaction, the tetrahydrofuran was removed by distillation under reduced pressure. The residue was extracted by adding 50 mL of water and 50 mL of dichloromethane to the residue. The organic phase was separated and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The crude product was recrystallized by dichloromethane and cyclohexane to give 3.33 g of 1-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazol-[4,3-A]pyrazine-7(8H)-yl)-4-(2,4,5-trifluorophenyl)-1,3-butanedione in 82% yield and 99% purity.

[References]

[1] Patent: CN108178761, 2018, A. Location in patent: Paragraph 0032; 0038; 0039; 0061-0066
Spectrum DetailBack Directory
[Spectrum Detail]

(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)butan-2-one(764667-65-4)1HNMR
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