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847445-81-2

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  • 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/ LIDE PHARMA- Factory supply / Best price

    Cas No: 847445-81-2

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  • 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)- 847445-81-2

    Cas No: 847445-81-2

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  • 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)-

    Cas No: 847445-81-2

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847445-81-2 Usage

General Description

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)- is a chemical compound with a complex molecular structure. It contains a triazolo-pyrazine ring and an amino-oxo-butene side chain with a trifluorophenyl group, as well as tetrahydro and trifluoromethyl substituents. 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)- possesses potential pharmaceutical properties due to its unique structure, and may be used in medicinal chemistry research for the development of new drugs with therapeutic applications. However, further studies and testing are required to fully understand its biological activity and potential uses.

Check Digit Verification of cas no

The CAS Registry Mumber 847445-81-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,4,7,4,4 and 5 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 847445-81:
(8*8)+(7*4)+(6*7)+(5*4)+(4*4)+(3*5)+(2*8)+(1*1)=202
202 % 10 = 2
So 847445-81-2 is a valid CAS Registry Number.

847445-81-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one

1.2 Other means of identification

Product number -
Other names 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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:847445-81-2 SDS

847445-81-2Synthetic 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

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

dehydrositagliptin
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;
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
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

dehydrositagliptin
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
ammonia
7664-41-7

ammonia

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
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

dehydrositagliptin
847445-81-2

dehydrositagliptin

Conditions
ConditionsYield
With ammonium acetate In methanol; water at 0 - 45℃; for 0.25 - 0.5h;
(2,4,5-trifluorophenyl)acetic acid
209995-38-0

(2,4,5-trifluorophenyl)acetic acid

dehydrositagliptin
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

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

dehydrositagliptin
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
4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid
1256815-03-8

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

dehydrositagliptin
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

C15H16F3NO4

dehydrositagliptin
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

C21H21F6N5O3

dehydrositagliptin
847445-81-2

dehydrositagliptin

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

dehydrositagliptin

(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
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
dehydrositagliptin
847445-81-2

dehydrositagliptin

sitagliptin
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
dehydrositagliptin
847445-81-2

dehydrositagliptin

(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

sitagliptin (R)-(-)mandelate
1240038-86-1

sitagliptin (R)-(-)mandelate

Conditions
ConditionsYield
With hydrogen In water; isopropyl alcohol at 20 - 25℃; under 760.051 - 1520.1 Torr; for 4h; Autoclave; Inert atmosphere;35.6%
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

(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
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

B

(R/S)-3-hydroxy-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
1253056-01-7

(R/S)-3-hydroxy-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
ConditionsYield
With sodium tetrahydroborate; methanesulfonic acid In tetrahydrofuran; isopropyl alcohol at -5 - 5℃;
dehydrositagliptin
847445-81-2

dehydrositagliptin

acetic acid
64-19-7

acetic acid

A

(R)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[ 4,3-a]pyrazin-7(8H)yl)-4-(2,4,5-trifluoro phenyl)butan-1-one acetate
1169707-34-9

(R)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[ 4,3-a]pyrazin-7(8H)yl)-4-(2,4,5-trifluoro phenyl)butan-1-one acetate

B

C32H25F12N9O2

C32H25F12N9O2

Conditions
ConditionsYield
With Ru(OAc)2(S)-DM-SegPhos; hydrogen In methanol at 80℃; under 14997.7 Torr; for 15h; optical yield given as %ee; enantioselective reaction;A 32 %Chromat.
B n/a
dehydrositagliptin
847445-81-2

dehydrositagliptin

salicylic acid
69-72-7

salicylic acid

sitagliptin salicylate

sitagliptin salicylate

Conditions
ConditionsYield
With Ru(OAc)2(S)-DM-SegPhos; hydrogen; ammonium salicylate In methanol at 80℃; under 14997.7 Torr; for 15h; optical yield given as %ee; enantioselective reaction;96 %Chromat.
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

(S)-Sitagliptin

(S)-Sitagliptin

B

sitagliptin
486460-32-6

sitagliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol / 2 h / 20 °C
3: sodium hydrogencarbonate / water; methanol
View Scheme
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 1,1-bis[(2R,5R)-2,5-diethylphospholano]ferrocene; hydrogen; ammonium chloride In methanol at 70℃; under 22502.3 Torr; for 24h; Catalytic behavior; Pressure; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Autoclave; enantioselective reaction;A n/a
B n/a
dehydrositagliptin
847445-81-2

dehydrositagliptin

(2R/2S)-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 (-)dibenzolyl-L-tartaric acid salt

(2R/2S)-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 (-)dibenzolyl-L-tartaric acid salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol / 2 h / 20 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

(2R)-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 (-)dibenzolyl-L-tartaric acid salt
1190094-97-3

(2R)-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 (-)dibenzolyl-L-tartaric acid salt

B

(2S)-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 (-)dibenzolyl-L-tartaric acid salt
1219440-27-3

(2S)-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 (-)dibenzolyl-L-tartaric acid salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: isopropyl alcohol; methanol / 1 h / 60 - 65 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

dibenzoyl-D-tartaric acid (2R)-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
1219440-25-1

dibenzoyl-D-tartaric acid (2R)-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

B

dibenzoyl-D-tartaric acid (2S)-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
1219440-26-2

dibenzoyl-D-tartaric acid (2S)-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
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: isopropyl alcohol; methanol / 1 h / 60 - 65 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

L-tartaric acid (2R)-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
862156-85-2

L-tartaric acid (2R)-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
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol / 3 h / 60 - 65 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

(S)-(+)-O-acetylmandelic acid (2R)-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
1219440-29-5

(S)-(+)-O-acetylmandelic acid (2R)-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

B

(S)-(+)-O-acetylmandelic acid (2S)-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
1219440-30-8

(S)-(+)-O-acetylmandelic acid (2S)-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
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: water / 17 h / 60 - 65 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

dibenzoyl-D-tartaric acid 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

dibenzoyl-D-tartaric acid 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
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

(2R)-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 phosphate

(2R)-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 phosphate

B

(2S)-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 phosphate

(2S)-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 phosphate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol
3: sodium hydrogencarbonate / water; methanol
4: phosphoric acid / isopropyl alcohol / 70 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: dimethylsulfide borane complex; methanesulfonic acid / isopropyl alcohol; tetrahydrofuran / 4 h / -10 - -5 °C
2: methanol / 2 h / 20 °C
3: sodium hydrogencarbonate / water; methanol
4: phosphoric acid / isopropyl alcohol / 70 - 75 °C
View Scheme
Multi-step reaction with 4 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
4: phosphoric acid / isopropyl alcohol / 70 - 75 °C
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

(2R)-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 phosphate

(2R)-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 phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen; ammonium salicylate / [RhCl2(p-cymene)]2; (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene / 2,2,2-trifluoroethanol / 24 h / 50 °C / 22502.3 Torr / Autoclave
2: phosphoric acid / methanol
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

A

C32H25F12N9O2

C32H25F12N9O2

B

sitagliptin
486460-32-6

sitagliptin

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen; ammonium chloride In methanol at 50℃; under 5947.36 Torr; for 16h; enantioselective reaction;
dehydrositagliptin
847445-81-2

dehydrositagliptin

sitagliptin phosphate

sitagliptin phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen; ammonium chloride / methanol / 16 h / 50 °C / 5947.36 Torr
2: phosphoric acid / water; isopropyl alcohol
View Scheme
dehydrositagliptin
847445-81-2

dehydrositagliptin

C16H11F6N5O

C16H11F6N5O

Conditions
ConditionsYield
With hydroxylamine hydrochloride In N,N-dimethyl-formamide at 60 - 70℃; for 6h;0.5 g

847445-81-2Downstream Products

847445-81-2Relevant articles and documents

Sitagliptin derivative or pharmaceutically acceptable salt, as well as preparation method and application thereof

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Paragraph 0119, (2018/04/01)

The invention relates to a sitagliptin derivative or pharmaceutically acceptable salt, as well as a preparation method and application thereof, and belongs to the technical field of synthesis of a medicine intermediate. In order to solve the problem that the conventional chain easily generates low-energy conformation, the invention provides the sitagliptin derivative or pharmaceutically acceptablesalt, and the preparation method thereof. The method comprises the following steps: under the existence of a coupling agent, performing coupling reaction on an enamine intermediate and a triazol[4,3-a]pyrazine compound to obtain an intermediate; performing deprotection reaction on the intermediate to remove a Boc group, and performing cyclization reaction on the hydroxylamine hydrochloride to obtain the corresponding sitagliptin derivative or pharmaceutically acceptable salt. Amino and carbonyl in flexible chain alkyl in the molecular structure are cyclized to form a five-membered ring structure, so that low-energy isomerism phenomena are effectively reduced, medicine stability is improved, and selectivity and medicine use safety are improved. The synthesis method is simple, and use of anexpensive chiral reagent can be avoided.

IMPROVED PROCESS FOR PREPARATION OF (2R)-4-OXO-4-[3- (TRIFLUOROMETHYL)-5,6-DIHYDRO [1,2,4]-TRIAZOLO[4,3-A]PYRAZIN- 7(8H)-YL]-L-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE and NEW IMPURITIES IN PREPARATION THEREOF

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Page/Page column 32, (2010/04/25)

The present invention relates to synthesis of β-amino acid derivatives of formula (I) and its salts of formula (Ia) by a novel process. The process comprises the reduction of a protected or unprotected prochiral β-amino acrylic acid or derivative there of, by using borane containing reducing agents at atmospheric pressure. The resulting racemic β-amino compound is resolved to a pure stereoisomer of formula (I), specifically to (2R)-4-oxo-4- [3-Ctrifluoromethyl)-5, 6-dihydrol [1,2,4]triazolo [4,3-alpyrazin-7(8H)-yl]-1-(2,4,4-trifluorophenyl)butan-2-amine. In an embodiment the invention disclosed polymorphic forms of formula (I), phosphate salt of formula (I) and also a Dibenzoyl-L-tartaric acid salt of formula (I).

A PROCESS FOR THE PREPARATION OF R-SIT AGLIPTIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

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Page/Page column 23-24, (2009/08/14)

The present invention provides processes for the preparation of R-sitagliptin and its pharmaceutically acceptable salts thereof.

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