Prasugrel supplier | CasNO.150322-43-3

Name
Prasugrel
EINECS 801-962-1
CAS No. 150322-43-3
Article Data51
CAS DataBase
Density 1.347 g/cm³
Solubility
Melting Point 120.0 to 124.0 °C
Formula C₂₀H₂₀FNO₃S
Boiling Point 493.5 °C at 760 mmHg
Molecular Weight 373.448
Flash Point 252.3 °C
Transport Information
Appearance White solid
Safety 24/25
Risk Codes
Molecular Structure
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;
PSA 74.85000
LogP 3.82890

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With acetic anhydride In N-methyl-acetamide; mineral oil	65%
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran; ethanol; acetic anhydride

...Expand

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In isopropyl alcohol at 20 - 50℃; Product distribution / selectivity;	89%

: 150322-43-3
prasugel

: 1191933-01-3
prasugrel monohydrogensulfate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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.

Product Name

Prasugrel

Synthetic route

Prasugrel Chemical Properties

Prasugrel History

Prasugrel Uses

Prasugrel Specification

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