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847445-81-2

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Basic Information
CAS No.: 847445-81-2
Name: 1,2,4-Triazolo[4,3-a]pyrazine, 7-[3-amino-1-oxo-4-(2,4,5-trifluorophenyl)-2-butenyl]-5,6,7,8-tetrahydro- 3-(trifluoromethyl)-
Article Data: 7
Molecular Structure:
Molecular Structure of 847445-81-2 (1,2,4-Triazolo[4,3-a]pyrazine, 7-[3-amino-1-oxo-4-(2,4,5-trifluorophenyl)-2-butenyl]-5,6,7,8-tetrahydro- 3-(trifluoromethyl)-)
Formula: C16H13F6N5O
Molecular Weight: 405.303
Synonyms: 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one;7-(1-oxo-3-amino-4-(2,4,5-trifluorophenyl)but-2-enyl)-3-trifluoromethyl-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine;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;(2E/Z)-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;
Density: 1.60
PSA: 77.04000
LogP: 2.77990
Related products
Synthetic route

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 sodium salt

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
With ammonium hydroxide; ammonium acetate; acetic acid In methanol; water at 60 - 65℃; for 6h; Product distribution / selectivity; Reflux;88.4%
With ammonium hydroxide; ammonium acetate; acetic acid In methanol; water at 60 - 65℃; for 6h; Product distribution / selectivity;
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

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
With ammonium acetate; ammonia In methanol; water at 55℃; for 6h;75%
With ammonium acetate; ammonia In methanol; water at 0 - 45℃;
With ammonium acetate
7664-41-7

ammonia

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

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
With ammonium acetate In methanol; water at 0 - 45℃; for 0.25 - 0.5h;
209995-38-0

(2,4,5-trifluorophenyl)acetic acid

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap / acetonitrile / 25 - 30 °C
1.2: 30 - 50 °C
2.1: ammonium hydroxide; ammonium acetate; acetic acid / water; methanol / 6 h / 60 - 65 °C
View Scheme

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

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap / acetonitrile / 25 - 30 °C
1.2: 30 - 50 °C
2.1: ammonium hydroxide; ammonium acetate; acetic acid / water; methanol / 6 h / 60 - 65 °C
View Scheme
1256815-03-8

4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 20 °C / Molecular sieve
2.1: benzotriazol-1-ol / dichloromethane / 0.17 h / 0 °C
2.2: 14 h / 20 °C
3.1: hydrogenchloride / isopropyl alcohol / 4 h / 35 - 40 °C
View Scheme

C15H16F3NO4

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: benzotriazol-1-ol / dichloromethane / 0.17 h / 0 °C
1.2: 14 h / 20 °C
2.1: hydrogenchloride / isopropyl alcohol / 4 h / 35 - 40 °C
View Scheme

C21H21F6N5O3

847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 35 - 40℃; for 4h;0.9 g
847445-81-2

dehydrositagliptin

823817-56-7

(R/S)-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-amine

Conditions
ConditionsYield
Stage #1: dehydrositagliptin With methanesulfonic acid; dimethylsulfide borane complex In tetrahydrofuran; isopropyl alcohol at -10 - -5℃; for 4h;
Stage #2: With ammonium hydroxide In tetrahydrofuran; water; isopropyl alcohol Product distribution / selectivity;		100%
Stage #1: dehydrositagliptin With methanesulfonic acid; dimethylsulfide borane complex In tetrahydrofuran; isopropyl alcohol at -10 - -5℃; for 4h;
Stage #2: With ammonia In tetrahydrofuran; water; isopropyl alcohol Product distribution / selectivity;		100%
With hydrogenchloride; sodium cyanoborohydride In methanol at 30℃; for 5h; pH=4.5;99.9%
With sodium cyanoborohydride; acetic acid In methanol; dichloromethane at -5 - 30℃;
Stage #1: dehydrositagliptin With sodium cyanoborohydride; acetic acid In methanol; dichloromethane at -5 - 30℃; Inert atmosphere;
Stage #2: With ammonia In water
847445-81-2

dehydrositagliptin

486460-32-6

sitagliptin

Conditions
ConditionsYield
With C44H42O8P2Ru; hydrogen; ammonium salicylate; salicylic acid In toluene at 75℃; under 12153.3 Torr; for 20h; Solvent; Reagent/catalyst; Pressure; Temperature; Inert atmosphere;62%
Multi-step reaction with 3 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol
3: sodium hydrogencarbonate / water; methanol
View Scheme
Multi-step reaction with 3 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol / 3 h / 60 - 65 °C
3: sodium hydrogencarbonate / ethyl acetate; water
View Scheme
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