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Prasugrel

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Name

Prasugrel

EINECS 801-962-1
CAS No. 150322-43-3 Density 1.347 g/cm3
PSA 74.85000 LogP 3.82890
Solubility Melting Point 120.0 to 124.0 °C
Formula C20H20FNO3S Boiling Point 493.5 °C at 760 mmHg
Molecular Weight 373.44 Flash Point 252.3 °C
Transport Information Appearance White solid
Safety 24/25 Risk Codes
Molecular Structure Molecular Structure of 150322-43-3 (Prasugrel) Hazard Symbols
Synonyms

2-[2-(Acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone;CS 747;CS-747;LY 640315;UNII-34K66TBT99;

 

Prasugrel Synthetic route

150322-38-6

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

75-36-5

acetyl chloride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one; acetyl chloride With acetic acid In toluene at 20℃; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In water; toluene
99%
With D201 macroporous strong basic styrene anion exchange resin, average particle diameter: 1.0 mm In tetrahydrofuran at 45℃; for 1.5h; Reagent/catalyst; Temperature;87.1%
952340-38-4

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

75-36-5

acetyl chloride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine; acetyl chloride With acetic acid In toluene at 20℃; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In water; toluene Product distribution / selectivity;
99%
150322-38-6

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
With triethylamine; sodium hydroxide In water; ethyl acetate at 7 - 50℃; pH=2.8; Temperature; pH-value;92.58%
With triethylamine In dichloromethane for 3h; Reflux;90.2%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 4h; Temperature; Reagent/catalyst; Solvent;83.2%
952340-38-4

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine With dmap; triethylamine In acetone at 0℃; for 0.166667h;
Stage #2: acetic anhydride In acetone Solvent; Temperature;
90%
With triethylamine; dmap In acetonitrile at -15℃; for 1h;
Stage #1: 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine With dmap; triethylamine In acetonitrile at 20℃; for 0.25h;
Stage #2: acetic anhydride In acetonitrile at 20℃;
With dmap; triethylamine In acetonitrile at 0℃;
With dmap; triethylamine In acetonitrile at -4 - -3℃; for 2.25h;

1-cyclopropyl-2-(2-fluorophenyl)-2-(2-hydroxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃;85%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;85%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15 - 25℃;46%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;
1243654-57-0

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide With triethylamine In dichloromethane at 0 - 5℃; for 0.5h;
Stage #2: acetic anhydride In dichloromethane
73%
Stage #1: 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide With triethylamine In dichloromethane at 25 - 30℃; for 0.25h;
Stage #2: acetic anhydride In dichloromethane at 0 - 5℃; for 6h;
Stage #1: 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide With triethylamine In dichloromethane at 25 - 30℃; for 0.25h;
Stage #2: acetic anhydride In dichloromethane at 0 - 5℃; for 6h;
With triethylamine In dichloromethane at 0℃; for 3.5h;
389574-20-3

prasugrel maleate salt

150322-43-3

prasugel

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 0.25h; pH=6.8; Solvent;68.5%

C20H24FNO4

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
With zinc sulfide; acetic acid; triethylamine In tetrahydrofuran at -10 - 55℃; for 8h; Green chemistry;68.5%
150322-38-6

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

150322-43-3

prasugel

Conditions
ConditionsYield
With acetic anhydride In N-methyl-acetamide; mineral oil65%
With acetic anhydride; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3.5h;65%
Multi-step reaction with 2 steps
1.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C
2.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C
2.2: 6 h / 0 - 5 °C
View Scheme
204205-33-4

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone

178688-49-8

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate With N-ethyl-N,N-diisopropylamine In acetonitrile at 30℃; for 0.5h;
Stage #2: acetic anhydride With N-ethyl-N,N-diisopropylamine; dmap In acetonitrile Product distribution / selectivity;
60.3%
150322-38-6

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

108-22-5

Isopropenyl acetate

150322-43-3

prasugel

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 65 - 70℃; for 3.5h;59.72%
204205-33-4

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone

952340-39-5

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1.5h;
Stage #2: acetic anhydride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15 - 20℃; for 1h;
55%
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1.5h; Cooling with ice;
Stage #2: acetic anhydride In N,N-dimethyl-formamide at 20℃; for 1h;
55%
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1.5h; Cooling;
Stage #2: acetic anhydride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15 - 20℃; for 1h;
55%
204205-33-4

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone

1151904-84-5

4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride

150322-43-3

prasugel

Conditions
ConditionsYield
With triethylamine In dichloromethane at -15 - 20℃; Product distribution / selectivity;36.6%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25 - 30℃; for 2 - 3h; Product distribution / selectivity;
204205-33-4

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone

1190589-93-5

2-acetoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine p-toluenesulfonate

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-acetoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine p-toluenesulfonate With sodium hydrogencarbonate In N,N-dimethyl-formamide at 5 - 10℃;
Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In N,N-dimethyl-formamide at 20℃; for 5h;
Stage #3: acetic anhydride In N,N-dimethyl-formamide at 20℃; for 3h;
32.85%
204205-33-4

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone

951380-43-1

2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1.5h;
Stage #2: acetic anhydride With N-ethyl-N,N-diisopropylamine; dmap In acetonitrile at 20℃; for 2h;
29%
1100905-46-1

3-cyclopropyl-1-(2-fluorophenyl)-3-oxopropyl methanesulfonate

951380-43-1

2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
Stage #1: 3-cyclopropyl-1-(2-fluorophenyl)-3-oxopropyl methanesulfonate; 2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride With tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1.5h;
Stage #2: acetic anhydride With N-ethyl-N,N-diisopropylamine; dmap In acetonitrile at 20℃; for 2h;
12%
952340-38-4

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

Conditions
ConditionsYield
With acetic acid In acetyl chloride; toluene
With p-toluenesulfonic acid monohydrate; acetic anhydride; acetic acid In toluene
With p-toluenesulfonic acid monohydrate; acetic anhydride In toluene
Multi-step reaction with 2 steps
1: hydrogenchloride; water / ethyl acetate / 20 °C
2: acetic acid / toluene / 20 °C / Inert atmosphere
View Scheme
aqueous potassium dihydrogen phosphate

aqueous potassium dihydrogen phosphate

potassium dihydrogen phosphate

952340-38-4

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran; ethanol; acetic anhydride
aqueous potassium dihydrogen phosphate

aqueous potassium dihydrogen phosphate

952340-38-4

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

Conditions
ConditionsYield
With dmap; triethylamine In acetic anhydride; acetonitrile

2-(tert-butyldiphenylsilyloxy)-5-(α-cyclopropyl-carbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

2-triisopropylsilyloxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine fumarate

150322-43-3

prasugel

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 0.5h; Purification / work up;
1190589-94-6

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 1.25h;
951380-42-0

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

108-24-7

acetic anhydride

150322-43-3

prasugel

Conditions
ConditionsYield
dmap In acetonitrile at 22 - 25℃;
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 4h; Inert atmosphere;
With triethylamine In N,N-dimethyl-formamide at -10 - 20℃; for 2.5h; Inert atmosphere;
With triethylamine In N,N-dimethyl-formamide at -10 - 20℃; for 2.5h; Inert atmosphere;
109904-26-9

5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice-water bath
2: hydrogenchloride / diethyl ether
3: triethylamine / dichloromethane / -15 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetone / 0.42 h / 25 - 30 °C
2.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
2.2: 7 h / 25 - 30 °C
2.3: 8 h / 0 - 25 °C
3.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C
3.2: 6 h / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride; water / acetone / 3 h / 25 - 30 °C
2.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
2.2: 6 h / 25 - 30 °C
2.3: 6.5 h / 0 - 30 °C
View Scheme

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

150322-43-3

prasugel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
1.2: 1 h / -78 °C
1.3: 1 h / -60 - 0 °C
2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
1.2: 1 h / -78 °C
1.3: 1 h / -60 - 0 °C
2.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C
3.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C
3.2: 6 h / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere
1.2: 1 h / -10 - 0 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C
View Scheme
28783-41-7

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride

150322-43-3

prasugel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
2.2: 1 h / -78 °C
2.3: 1 h / -60 - 0 °C
3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
2.2: 1 h / -78 °C
2.3: 1 h / -60 - 0 °C
3.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C
4.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C
4.2: 6 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 9 h / 0 - 5 °C
2.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere
2.2: 1 h / 0 - 15 °C / Inert atmosphere
2.3: 2 h / 0 - 30 °C
3.1: hydrogenchloride; water / acetone / 3 h / 25 - 30 °C
4.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
4.2: 6 h / 25 - 30 °C
4.3: 6.5 h / 0 - 30 °C
View Scheme
150322-73-9

1-cyclopropyl-2-(2-fluorophenyl)ethanone

150322-43-3

prasugel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
2.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
3.2: 1 h / -78 °C
3.3: 1 h / -60 - 0 °C
4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
2.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
2.2: 6 h / 25 - 30 °C
2.3: 6.5 h / 0 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
2.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
2.2: 7 h / 25 - 30 °C
3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
451-82-1

(2-fluorophenyl)acetic acid

150322-43-3

prasugel

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 6 h / 0 - 5 °C
2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C
2.2: 40 - 50 °C
2.3: 0.25 h / 0 - 30 °C
3.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
4.1: potassium carbonate / acetonitrile / 5 h / 25 - 35 °C
5.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
5.2: 1 h / -78 °C
5.3: 1 h / -60 - 0 °C
6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 6 h / 0 - 5 °C
2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C
2.2: 40 - 50 °C
2.3: 0.25 h / 0 - 30 °C
3.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
4.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
4.2: 6 h / 25 - 30 °C
4.3: 6.5 h / 0 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 6 h / 0 - 5 °C
2.1: iodine; magnesium / tetrahydrofuran / 25 - 50 °C
2.2: 40 - 50 °C
2.3: 0.25 h / 0 - 30 °C
3.1: toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 4 h / Reflux
4.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C
4.2: 7 h / 25 - 30 °C
5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C
View Scheme
150322-43-3

prasugel

CS-747 hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In di-isopropyl ether; water; ethyl acetate at 20℃; Inert atmosphere;99%
With hydrogenchloride In tetrahydrofuran at -5 - 20℃; for 16h; Solvent; Temperature; Concentration;98%
With acetyl chloride; tert-butyl alcohol In acetone at 20℃; Reagent/catalyst; Solvent;98.2%
150322-43-3

prasugel

1060616-79-6

prasugrel hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In acetone at 5 - 10℃; for 1h; Product distribution / selectivity;99%
With hydrogen bromide In water; acetone at 5 - 10℃; for 1h; Product distribution / selectivity;99%
With Acetyl bromide; acetic acid In ethyl acetate at 20 - 60℃; for 5.33333h; Product distribution / selectivity;89%
81-04-9

naphthalene-1,5-disulfonate

150322-43-3

prasugel

prasugrel 1,5-naphthalene disulfonate

Conditions
ConditionsYield
In acetone at 20℃; for 6h; Product distribution / selectivity;96%
98-11-3

benzenesulfonic acid

150322-43-3

prasugel

952340-40-8

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate benzene sulfonate

Conditions
ConditionsYield
In diethyl ether; acetone at -10 - 35℃; for 12h;93%
In diethyl ether; acetone at 20℃;93%
In acetone at 30℃; for 6h; Product distribution / selectivity;79%
In methanol Product distribution / selectivity;
64-19-7

acetic acid

150322-43-3

prasugel

5-[(1RS)-2-cyclopropyl-1-(2-fluorophenyl)-2-oxyethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-yl acetate acetic acid hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In water at 40℃; for 0.166667h; Solvent;92.2%
110-16-7

maleic acid

150322-43-3

prasugel

389574-20-3

prasugrel maleate salt

Conditions
ConditionsYield
In acetone at 25 - 30℃; for 3h; Concentration;89.84%
110-04-3

ethane-1,2-disulphonic acid

150322-43-3

prasugel

prasugrel 1,2-ethane disulfonate

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 50℃; Product distribution / selectivity;89%
150322-43-3

prasugel

1191933-01-3

prasugrel monohydrogensulfate

Conditions
ConditionsYield
With sulfuric acid In acetone at -5℃; for 1.25h;86%
With sulfuric acid In isopropyl alcohol at 20℃; for 6h; Product distribution / selectivity;84%
With sulfuric acid In acetone at -32 - -28℃; for 5.5h; Product distribution / selectivity;78%
150322-43-3

prasugel

C20H18(2)H2FNO3S

Conditions
ConditionsYield
With [(2)H6]acetone; tris(pentafluorophenyl)borate In toluene at 150℃; for 6h; Inert atmosphere;85%
150322-43-3

prasugel

2-acetyloxy-5-(α-cycloproylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine bisulfate

Conditions
ConditionsYield
With sulfuric acid In water; acetone at -32 - -28℃; for 5.5h; Product distribution / selectivity;78%
81-04-9

naphthalene-1,5-disulfonate

150322-43-3

prasugel

prasugrel 1,5-naphthalenedisulfonic acid salt

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 50℃; Product distribution / selectivity;75%
In acetone at 20℃;
150322-43-3

prasugel

1060616-82-1

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydroiodide

Conditions
ConditionsYield
With hydrogen iodide In water; acetone at 5 - 10℃; for 1.5h;74%
With hydrogen iodide In water; acetone at 5 - 10℃; for 1.5h;74%
75-75-2

methanesulfonic acid

150322-43-3

prasugel

1060616-84-3

prasugrel mesylate salt

Conditions
ConditionsYield
In acetone at 20 - 26℃; Cooling;70%
In methanol Product distribution / selectivity;
120-18-3

naphthalene-2-sulfonate

150322-43-3

prasugel

1178975-69-3

prasugrel 2-naphthalenesulfonic acid salt

Conditions
ConditionsYield
In acetone at 20℃; for 0.75h; Product distribution / selectivity;69%
In methanol Product distribution / selectivity;
85-47-2

1-naphthalenesulfonic acid

150322-43-3

prasugel

1178975-73-9

prasugrel 1-naphthalenesulfonic acid salt

Conditions
ConditionsYield
In acetone at 20℃; for 0.333333h;66%
In acetone at 20℃;
100-88-9

cyclohexylsulfamic acid

150322-43-3

prasugel

1306607-31-7

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate cyclamate

Conditions
ConditionsYield
In acetone at -10℃; for 12h;45%
In acetone45%

Prasugrel Chemical Properties

Molecular structure of Prasugrel  (CAS NO.150322-43-3) is:

Product Name: Prasugrel
CAS Registry Number: 150322-43-3
IUPAC Name: [5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-6,7-dihydro-4H-thieno[3,2-c]pyridin-2-yl] acetate
Molecular Weight: 373.441103 [g/mol]
Molecular Formula: C20H20FNO3S
XLogP3-AA: 3.6
H-Bond Donor: 0
H-Bond Acceptor: 5 
Surface Tension: 56.7 dyne/cm
Density: 1.347 g/cm3
Flash Point: 252.3 °C
Enthalpy of Vaporization: 76.06 kJ/mol
Boiling Point: 493.5 °C at 760 mmHg
Vapour Pressure: 7.01E-10 mmHg at 25°C
Classification Code: Platelet Aggregation Inhibitors

Prasugrel History

  Prasugrel (marketing name Effient in the US and Efient in EU) is a novel platelet inhibitor developed by Daiichi Sankyo Co. and produced by Ube and currently under clinical development in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). The U.S. Food and Drug Administration approved Effient tablets for the reduction of thrombotic cardiovascular events in July 10, 2009.

Prasugrel Uses

 Prasugrel (CAS NO.150322-43-3) can be used as a novel platelet inhibitor.And it is a P2Y(12) receptor antagonist with antiplatelet activity.

Prasugrel Specification

 Prasugrel , its cas register number is 150322-43-3. It also can be called 2-[2-(Acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone .It is a member of the thienopyridine class of ADP receptor inhibitors. And it produces inhibition of platelet aggregation to 20 μM or 5 μM ADP, as measured by light transmission aggregometry.

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