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

Name
3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
EINECS 616-309-4
CAS No. 762240-92-6
Article Data30
CAS DataBase
Density
Solubility
Melting Point 236-246oC
Formula C₆H₇F₃N₄.HCl
Boiling Point 266.2 °C at 760 mmHg
Molecular Weight 228.605
Flash Point 114.8 °C
Transport Information
Appearance white solid
Safety 45
Risk Codes 25
Molecular Structure
Hazard Symbols T
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In water; ethyl acetate for 0.166667h; Product distribution / selectivity;	99%

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: C6H6F3N4(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium hydroxide In water; ethyl acetate for 0.166667h; Product distribution / selectivity;	99%

: 939412-86-9
C-(3-chloropyrazin-2-yl)-methylamine hydrochloride salt

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1326282-23-8
N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide

Conditions

Conditions	Yield
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With N-ethyl-N,N-diisopropylamine; trichloromethyl chloroformate In tetrahydrofuran at 0℃; for 1h; Stage #2: C-(3-chloropyrazin-2-yl)-methylamine hydrochloride salt With triethylamine In dichloromethane for 3h;	99%

: 764667-64-3
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

Conditions

Conditions	Yield
With 4-methyl-morpholine In ethyl acetate for 6h; Reflux;	98.1%
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 85℃; for 4h;	93.3%
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 85℃; for 3.5h;	92%

: 1215221-92-3
4-Chloro-6-ethyl-thieno[2,3-d]pyrimidine-2-carboxylic acid methyl ester

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1215221-93-4
6-Ethyl-4-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)thieno[2,3-d]pyrimidine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 16h; Reflux;	98%

: 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

: Sitagliptin hydrochloride

Conditions

Conditions	Yield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl-formamide for 0.166667h; Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In N,N-dimethyl-formamide at 20 - 25℃; for 5h; Reagent/catalyst;	97%

: 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

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In dichloromethane for 0.166667h; Stage #2: With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25 - 30℃; for 4h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride Further stages;	96.5%

: 4668-42-2
(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1404380-70-6
(S)-2-((benzyloxycarbonyl)amino)-4-oxo-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine)butanoic acid methyl ester

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; Reflux;	95%

: (4R)-4-(2,4,5-trifluorobenzyl)azetidin-2-one

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 2-Ethylhexanoic acid; triethylamine In tetrahydrofuran at 75℃; for 72h;	95%
With 2-Ethylhexanoic acid; triethylamine In tetrahydrofuran at 75℃; for 72h; Solvent; Temperature; Reagent/catalyst; Concentration;	95%

: 1380569-10-7
C17H16F3NO2

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1306610-49-0
C23H21F6N5O

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;	94%

: 1293293-73-8
(3R)-3-azido-4-(2,4,5-trifluorophenyl)-butyric acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1253055-98-9
(R)-3-azido-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

Conditions

Conditions	Yield
Stage #1: (3R)-3-azido-4-(2,4,5-trifluorophenyl)-butyric acid; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In water; N,N-dimethyl-formamide for 0.25h; Stage #2: With 4-methyl-morpholine In water; N,N-dimethyl-formamide at 10℃; for 0.166667h; Stage #3: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water; N,N-dimethyl-formamide at 0℃; for 1h;	93%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃;

: 1380243-46-8
C17H14F3NO3

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1380243-49-1
C23H19F6N5O2

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;	92%

: (4R)-4-(2,4,5-trifluorobenzyl)azetidin-2-one

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: Sitagliptin hydrochloride

Conditions

Conditions	Yield
In acetonitrile at 100℃; for 2h; Solvent; Temperature; Reagent/catalyst; Concentration;	92%

: 1380243-45-7
C17H16F3NO4S

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1380243-48-0
C23H21F6N5O3S

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;	91%

: C30H30F3NO4S2

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: C29H29F6N5O4S

Conditions

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 70℃; for 48h;	91%

: 22118-09-8
2-bromoacetyl chloride

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: C8H8BrF3N4O

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	91%

: 2033-24-1
cycl-isopropylidene malonate

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

Conditions

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 45 - 55℃; Large scale reaction; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 50 - 55℃; for 6h; Large scale reaction;	90%
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20 - 50℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl acetamide at 40 - 70℃; Stage #3: With sodium hydrogencarbonate In N,N-dimethyl acetamide; water at 20 - 45℃;	89%
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 50℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 40 - 55℃; for 6h;
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 0 - 40℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In ISOPROPYLAMIDE at 40 - 70℃;
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; Stage #2: With pivaloyl chloride In acetonitrile at 50℃; for 3.75h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 55℃; for 6h;

...Expand

: 1246960-25-7
(R)-3-(((benzyloxy)carbonyl)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

: 1242069-63-1
(R)-benzyl (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-yl)carbamate

Conditions

Conditions	Yield
Stage #1: (R)-3-(((benzyloxy)carbonyl)amino)-4-(2,4,5-trifluorophenyl)butanoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 0 - 5℃; for 1h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In tetrahydrofuran at 25℃; Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water	90%
Stage #1: (R)-3-(((benzyloxy)carbonyl)amino)-4-(2,4,5-trifluorophenyl)butanoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With triethylamine In tetrahydrofuran Reflux;
With triethylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

Conditions

Conditions	Yield
Stage #1: (2,4,5-trifluorophenyl)acetic acid With cycl-isopropylidene malonate; N-ethyl-N,N-diisopropylamine; dmap In ISOPROPYLAMIDE at 20 - 40℃; Stage #2: With pivaloyl chloride In ISOPROPYLAMIDE at 0 - 5℃; for 1 - 3h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In ISOPROPYLAMIDE at 40 - 70℃;	89%
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 0 - 40℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl acetamide at 40 - 70℃; for 1h;

: 1195-45-5
para-fluorophenyl isocyanate

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: N-(4-Fluorophenyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2, 4]triazolo [4,3-a]pyrazine-7-carboxamide

Conditions

Conditions	Yield
With triethylamine In toluene at 75 - 80℃; for 4h;	88.2%

: C10H7F3O2

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: (Z/E)-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-3-en-1-one

Conditions

Conditions	Yield
Stage #1: C10H7F3O2 With 1,1'-carbonyldiimidazole In ethyl acetate at 20℃; for 0.5h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With triethylamine In ethyl acetate at 20℃; Concentration;	87.2%

: 504-88-1
3-nitropropionic acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 3-nitro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)propan-1-one

Conditions

Conditions	Yield
Stage #1: 3-nitropropionic acid; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate; acetonitrile	85%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 20h;	79%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 20h;	79%

: 1215221-53-6
Acetic acid 2-acetoxy-3-(4-chloro-6-ethyl-thieno[2,3-d]pyrimidin-2-yloxy)-propyl ester

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1215221-54-7
acetic acid 2-acetoxy-3-[6-ethyl-4-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-thieno[2,3-d]pyrimidin-2-yloxy]-propyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 80℃; for 16h;	85%

: 1380243-47-9
C16H14F3NO4S

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 1380243-50-4
C22H19F6N5O3S

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;	85%

: 5-(2-(3-fluorophenyl)-1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 4-(3-fluorophenyl)-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)butane-1,3-dione

Conditions

Conditions	Yield
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With 4-methyl-morpholine In ethyl acetate at 40℃; Stage #2: 5-(2-(3-fluorophenyl)-1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione In ethyl acetate Reflux;	85%

: (2S)-2-[(t-butoxycarbonyl)amino]-3-{4-[(3-cyano pyridin-2-yl)oxy]phenyl}propanoic acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 2-{4-[(2S)-2-(t-butoxycarbonyl)amino-3-oxo-3-(3-(trifluoro methyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)propyl]phenoxy}nicotinonitrile

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 5h;	84.5%

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

Product Name

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

Synthetic route

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

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