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150322-43-3

Basic Information
CAS No.: 150322-43-3
Name: Prasugrel
Article Data: 51
Cas Database
Molecular Structure:
Molecular Structure of 150322-43-3 (Prasugrel)
Formula: C20H20FNO3S
Molecular Weight: 373.448
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;
EINECS: 801-962-1
Density: 1.347 g/cm3
Melting Point: 120.0 to 124.0 °C
Boiling Point: 493.5 °C at 760 mmHg
Flash Point: 252.3 °C
Solubility: N/A
Appearance: White solid
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 24/25
Transport Information: N/A
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
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%
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Chemistry

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

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.

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.

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.