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762240-92-6

Basic Information
CAS No.: 762240-92-6
Name: 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
Article Data: 30
Molecular Structure:
Molecular Structure of 762240-92-6 (3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride)
Formula: C6H7F3N4.HCl
Molecular Weight: 228.605
Synonyms: 1,2,4-Triazolo[4,3-a]pyrazine,5,6,7,8-tetrahydro-3-(trifluoromethyl)-, monohydrochloride (9CI);3-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazinemonohydrochloride;3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine HCl;
EINECS: 616-309-4
Melting Point: 236-246oC
Boiling Point: 266.2 °C at 760 mmHg
Flash Point: 114.8 °C
Appearance: white solid
Hazard Symbols: T
Risk Codes: 25
Safety: 45
PSA: 42.74000
LogP: 1.53090
Synthetic route
763105-70-0

2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide

762240-92-6

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

Conditions
ConditionsYield
With hydrogenchloride In methanol at 55℃; for 0.5h;92%
With hydrogenchloride In ethanol; water at 50 - 54℃; for 3.5h; Temperature;92.6%
With hydrogenchloride In isopropyl alcohol at 60 - 65℃; for 2h; Temperature; Inert atmosphere; Large scale;91%

piperazinylidene trifluoroacetohydrazide

762240-92-6

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

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 55 - 60℃; for 1h; Temperature; Solvent; Inert atmosphere;90.71%

1-trifluoroacetyl-2-piperazinone

762240-92-6

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

Conditions
ConditionsYield
Stage #1: 1-trifluoroacetyl-2-piperazinone With hydrazine In water at 50 - 55℃; for 3h;
Stage #2: With hydrogenchloride In water for 3h; Reflux;
86.2%
486460-20-2

3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine

762240-92-6

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

Conditions
ConditionsYield
Stage #1: 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine With palladium on activated carbon; hydrogen In methanol at 40 - 45℃; under 2625.26 - 3375.34 Torr; for 24h;
Stage #2: With hydrogenchloride In isopropyl alcohol at 0 - 5℃;
82.9%
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethanol / 45 °C / 3345.86 Torr / Large scale
2: hydrogenchloride / Isopropyl acetate / 1 h / 20 °C / Large scale
View Scheme
With palladium 10% on activated carbon; hydrogen In Isopropyl acetate at 40 - 45℃; under 2585.81 Torr;8 g
486460-21-3

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

762240-92-6

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

Conditions
ConditionsYield
With hydrogenchloride In Isopropyl acetate at 20℃; for 1h; Large scale;51%

(S)-Sitagliptin

A

1253056-11-9

sodium (S)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

B

762240-92-6

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

Conditions
ConditionsYield
Stage #1: (S)-Sitagliptin With water; sodium hydroxide In methanol at 25℃; Reflux;
Stage #2: With hydrogenchloride In methanol; water

(1,2)-bis-trifluoroacetyl-1-pyrazinylhydrazide

762240-92-6

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphoric acid / 5 h / 75 °C / Large scale
2: palladium 10% on activated carbon; hydrogen / ethanol / 45 °C / 3345.86 Torr / Large scale
3: hydrogenchloride / Isopropyl acetate / 1 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: polyphosphoric acid / 5 h / 130 - 135 °C
2: palladium 10% on activated carbon; hydrogen / Isopropyl acetate / 40 - 45 °C / 2585.81 Torr
View Scheme

2,2,2-trifluoro-N′-(pyrazin-2-yl)acetohydrazide

762240-92-6

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / 12 h / 0 - 85 °C
2.1: hydrogen; palladium on activated carbon / methanol / 24 h / 40 - 45 °C / 2625.26 - 3375.34 Torr
2.2: 0 - 5 °C
View Scheme
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

762240-92-6

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

486460-23-5

(R)-tert-butyl 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-ylcarbamate

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 55 - 60℃; for 12h;99.02%
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20 - 50℃; Reagent/catalyst; Solvent;96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;95%
762240-92-6

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

486460-21-3

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

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate for 0.166667h; Product distribution / selectivity;99%
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    762240-92-6

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Specification

The 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, with the CAS registry number 762240-92-6. This chemical's molecular formula is C6H8ClF3N4 and molecular weight is 228.6. What's more,Its systematic name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride.It is a White Solid and it is Sitagliptin intermediate.

Physical properties about 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride are:
(1)ACD/LogP:  -0.206; (2)# of Rule of 5 Violations:  0; (3)#H bond acceptors:  4; (4)#H bond donors:  1; (5)#Freely Rotating Bonds:  0; (6)Flash Point:  114.8 °C; (7)Enthalpy of Vaporization:  50.41 kJ/mol ; (8)Boiling Point:  266.2 °C at 760 mmHg; (9)Vapour Pressure:  0.00879 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Cl.FC(F)(F)c1nnc2n1CCNC2;
(2)Std. InChI:InChI=1S/C6H7F3N4.ClH/c7-6(8,9)5-12-11-4-3-10-1-2-13(4)5;/h10H,1-3H2;1H;
(3)Std. InChIKey:AQCSCRYRCRORET-UHFFFAOYSA-N.