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High quality Prasugrel 150322-43-399% with factory price 2-[2-(Acetyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]-1-cyclopropyl-2-(2-fluorophenyl)ethanone hydrochloride
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150322-43-3 Usage

General Description

Prasugrel (brand name: “efficient”), a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thus preventing activation of the GPIIb/IIIa receptor complex. As a result, inhibition of ADP-mediated platelet activation and aggregation occurs. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). FDA approved in 2009. Its brand name is “efficient”. Figure 1 Molecular structure of Prasugrel;

Chemical Properties

Prasugrel is usually formulated in the form of hydrochloride salt. Prasugrel hydrochloride has the empirical formula C20H20FNO3S?HCl representing a molecular weight of 409.90. Prasugrel hydrochloride is a white to practically white solid. It is soluble at pH 2, slightly soluble at pH 3 to 4, and practically insoluble at pH 6 to 7.5. It also dissolves freely in methanol and is slightly soluble in 1-and 2-propanol and acetone. It is practically insoluble in diethyl ether and ethyl acetate.

Application

Prasugrel is used in combination with low dose aspirin to prevent thrombosis in patients with acute coronary syndrome (ACS), including unstable angina pectoris, non-ST elevation myocardial infarction (NSTEMI), and ST elevation myocardial infarction (STEMI), who are planned for treatment with percutaneous coronary intervention (PCI). In studies, prasugrel was more effective than the related clopidogrel but also caused more bleeding. Overall mortality was the same. Prasugrel does not change the risk of death when given to people who have had a STEMI or NSTEMI. Prasugrel does however increase the risk of bleeding and may decrease the risk of further cardiovascular problems. Thus routine use in NSTEMI patients is of questionable value.

Mode of action

Prasugrel is an inhibitor of platelet activation and aggregation through the irreversible binding of its active metabolite to the P2Y12 class of ADP receptors on platelets.

Pharmacodynamics

Prasugrel is a member of the thienopyridine class of ADP receptor inhibitors, like ticlopidine (trade name Ticlid) and clopidogrel (trade name Plavix). These agents reduce the aggregation ("clumping") of platelets by irreversibly binding to P2Y12 receptors. Compared to clopidogrel, prasugrel inhibits adenosine diphosphate–induced platelet aggregation more rapidly, more consistently, and to a greater extent than do standard and higher doses of clopidogrel in healthy volunteers and in patients with coronary artery disease, including those undergoing PCI. The increased potency of prasugrel appears to be due to more efficient conversion to its active metabolite. However, it carries a higher risk of bleed compared to clopidogrel, which may be a result of its higher potency. Prasugrel produces inhibition of platelet aggregation to 20 μM or 5 μM ADP, as measured by light transmission aggregometry.

Administration and dosage

Initiate Effient (the brand name of prasugrel) treatment as a single 60 mg oral loading dose and then continue at 10 mg orally once daily. Patients taking Effient should also take aspirin (75 mg to 325 mg) daily.

Metabolism

Prasugrel is not detected in plasma following oral administration. It is rapidly hydrolyzed in the intestine to thiolactone by human carboxylesterase (hCE) 2. This intermediate is further metabolized to its active metabolite, R-138727, in a single step by cytochrome P450 enzymes in the liver (primarily CYP3A4 and CYP2B6 and to a lesser extent by CYP2C9 and CYP2C19). The active metabolite is further metabolized by S-methylation or cysteine conjugation to two inactive metabolites. Unlike clopidogrel, transformation of prasugrel to its active metabolite does not appear to be affected by cytochrome P450 polymorphisms.

Adverse reaction

Common adverse reactions include Bleeding, thrombotic Thrombocytopenic Purpura and Hypersensitivity Including Angioedema. In TRITON-TIMI 38, common and other important non-hemorrhagic adverse events were, for Effient and clopidogrel, respectively: severe thrombocytopenia (0.06%, 0.04%), anemia (2.2%, 2.0%), and abnormal hepatic function (0.22%, 0.27%), and allergic reactions (0.36%, 0.36%), and angioedema (0.06%, 0.04%).

Warning and precaution

CABG-related bleeding: Risk increases in patients receiving Effient who undergo CABG. Discontinuation of Effient: Premature discontinuation increases risk of stent thrombosis, MI, and death. Thrombotic thrombocytopenic purpura (TTP): TTP has been reported with Effient.

Contraindication

Prasugrel should not be given to patients with active pathological bleeding, such as peptic ulcer or a history of transient ischemic attack or stroke, because of higher risk of stroke (thrombotic stroke and intracranial hemorrhage).

Drug Interaction

Warfarin Co-administration of Effient and warfarin increases the risk of bleeding.? Non-Steroidal Anti-Inflammatory Drugs Co-administration of Effient and NSAIDs (used chronically) may increase the risk of bleeding. Other Concomitant Medications Effient can be administered with drugs that are inducers or inhibitors of cytochrome P450 enzymes. Effient can be administered with aspirin (75 mg to 325 mg per day), heparin, GPIIb/IIIa inhibitors, statins, digoxin, and drugs that elevate gastric pH, including proton pump inhibitors and H2 blockers.

Description

Prasugrel is a third-generation thienopyridine that has been developed and launched for the prevention of atherothrombotic events in patients with ACS or following PCI. While the second-generation agent clopidogrel was an improvement over the first-generation ticlopidine, which suffered from gastrointestinal adverse effects and the risk of neutropenia with prolonged use, its delayed onset of action and considerable interpatient variability prompted the search for the next-generation thienopyridine. The mechanism of action of these platelet inhibitors involves initial biological activation to a sulfhydryl metabolite that irreversibly binds to the P2γ12 receptor on platelets via disulfide formation, thereby preventing platelet activation and aggregation by the endogenous agonist adenosine diphosphate (ADP). The advantage of prasugrel over its predecessors is its more efficient and consistent absorption and rapid conversion to its active metabolite. Co-administration of thienopyridines with acetylsalicylic acid (aspirin), an inhibitor of the synthesis of the platelet aggregation mediator thromboxane A2, is an effective antiplatelet strategy and joins antagonists of glycoprotein IIb/IIIa, which target the final step in platelet aggregation, in the medical arsenal combating atherothrombotic events.

Originator

Daiichi Sankyo (Japan)

Uses

Prasugrel is a platelet inhibitor that reduces aggregation of platelets by being a P2Y12(ADP receptor) inhibitor.

Uses

Inhibits platelet aggregation (platelet ADPP 2Y12 antagonist).

Brand name

Effient

Clinical Use

Prasugrel is a platelet inhibitor developed by Daiichi Sankyo Co. and is marketed in the United States in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). Prasugrel was approved for use in Europe in February 2009, and is currently available in the UK. In the U.S. prasugrel is also approved for the reduction of thrombotic cardiovascular events, including stent thrombosis, in patients with acute coronary syndrome who are to be managed with PCI. Prasugrel is a member of the thienopyridine class of ADP receptor inhibitors, and irreversibly binds to P2Y12 receptors.

Side effects

In addition to the hemorrhagic side effect, other serious adverse events included AF, bradycardia, leucopenia, severe thrombocytopenia, angiodema, anemia, and abnormal hepatic function with hypertension, headache, back pain, dyspnea, nausea, dizziness, and diarrhea as less severe complaints. Prasugrel is contraindicated in patients with active pathological bleeding, such as peptic ulcers or intracranial hemorrhage, and in patients with a history of prior transient ischemic attack or stroke. In addition, in patients 75 years old, <60 kg, or likely to undergo urgent coronary artery bypass graft surgery, the risk may not outweigh the benefit. When possible, prasugrel treatment should be discontinued at least 7 days prior to any surgery. While warfarin and non-steroidal antiinflammatory drugs (NSAIDS) may increase the risk of bleeding with coadministration of prasugrel, no drug interactions are anticipated with concomitant use of drugs that are inducers or inhibitors of the cytochrome P450 enzymes. Prasugrel may also be administered with aspirin (75-325 mg per day), heparin, GP IIb/IIIa inhibitors, statins, digoxin, and drugs that elevate gastric pH, including PPIs and H2 blockers.

Chemical Synthesis

The synthesis of prasugrel begins with the preparation of the a-ketocyclopropane 102 which is prepared as summarized in the scheme. Conversion of 1-(bromomethyl)-2-fluorobenzene (99) to the corresponding Grignard reagent through reaction with magnesium followed by condensation with nitrile 100 resulted in ketone 101 in 72% yield. Chlorination of ketone 101 with CuCl2 resulted in the key prasugrel coupling component 102 in 92% yield. The piperidine coupling partner was prepared by treating thiolactone 103 with TBDMSCl and triethylamine to give thiophene 104 in 91% yield. Treatment of piperidine 104 with a-chloroketone 102 resulted in enol silane 105 in 65% yield. Reaction of silylenol ether 105 with acetic anhydride in the presence of triethylamine and catalytic DMAP resulted in the preparation of prasugrel (XVII) in 60% yield.

Drug interactions

Potentially hazardous interactions with other drugs Anticoagulants: enhanced anticoagulant effect with coumarins and phenindione.

Metabolism

Prasugrel is a prodrug and is rapidly metabolised in the liver by various cytochrome P450 enzymes to an active metabolite and inactive metabolites. The active metabolite is further metabolised to 2 inactive compounds which are excreted in the urine and faeces; about 68% of a dose is excreted in urine and about 27% in faeces.
InChI:InChI=1/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3

150322-43-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (P2040)  Prasugrel  >98.0%(HPLC)(T) 150322-43-3 200mg 880.00CNY Detail
Sigma (SML0331)  Prasugrel  ≥98% (HPLC) 150322-43-3 SML0331-10MG 941.85CNY Detail
Sigma (SML0331)  Prasugrel  ≥98% (HPLC) 150322-43-3 SML0331-50MG 3,803.67CNY Detail

150322-43-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Prasugrel

1.2 Other means of identification

Product number -
Other names Effient

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:150322-43-3 SDS

150322-43-3Synthetic route

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
150322-38-6

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

acetyl chloride
75-36-5

acetyl chloride

prasugel
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%
2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
952340-38-4

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

acetyl chloride
75-36-5

acetyl chloride

prasugel
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%
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
150322-38-6

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
952340-38-4

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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;
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide
1243654-57-0

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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;
prasugrel maleate salt
389574-20-3

prasugrel maleate salt

prasugel
150322-43-3

prasugel

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 0.25h; pH=6.8; Solvent;68.5%
C20H24FNO4

C20H24FNO4

acetic anhydride
108-24-7

acetic anhydride

prasugel
150322-43-3

prasugel

Conditions
ConditionsYield
With zinc sulfide; acetic acid; triethylamine In tetrahydrofuran at -10 - 55℃; for 8h; Green chemistry;68.5%
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
150322-38-6

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

prasugel
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
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
204205-33-4

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

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate
178688-49-8

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
150322-38-6

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

Isopropenyl acetate
108-22-5

Isopropenyl acetate

prasugel
150322-43-3

prasugel

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 65 - 70℃; for 3.5h;59.72%
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
204205-33-4

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

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate
952340-39-5

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
204205-33-4

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

4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride
1151904-84-5

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

prasugel
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;
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
204205-33-4

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

2-acetoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine p-toluenesulfonate
1190589-93-5

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
204205-33-4

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

2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride
951380-43-1

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
3-cyclopropyl-1-(2-fluorophenyl)-3-oxopropyl methanesulfonate
1100905-46-1

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

2-oxo-2,4,5,6,7a-hexahydrothieno[3,2-c]pyridine hydrochloride
951380-43-1

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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%
2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
952340-38-4

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

prasugel
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

potassium dihydrogen phosphate

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
952340-38-4

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

prasugel
150322-43-3

prasugel

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

aqueous potassium dihydrogen phosphate

2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
952340-38-4

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

prasugel
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

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

prasugel
150322-43-3

prasugel

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

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

prasugel
150322-43-3

prasugel

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

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

prasugel
150322-43-3

prasugel

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 0.5h; Purification / work up;
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide
1190589-94-6

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
150322-43-3

prasugel

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 1.25h;
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
951380-42-0

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

acetic anhydride
108-24-7

acetic anhydride

prasugel
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;
5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine
109904-26-9

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

prasugel
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

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

prasugel
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
6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride
28783-41-7

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

prasugel
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
1-cyclopropyl-2-(2-fluorophenyl)ethanone
150322-73-9

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

prasugel
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
(2-fluorophenyl)acetic acid
451-82-1

(2-fluorophenyl)acetic acid

prasugel
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
prasugel
150322-43-3

prasugel

CS-747 hydrochloride

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%
prasugel
150322-43-3

prasugel

prasugrel hydrobromide
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%
naphthalene-1,5-disulfonate
81-04-9

naphthalene-1,5-disulfonate

prasugel
150322-43-3

prasugel

prasugrel 1,5-naphthalene disulfonate

prasugrel 1,5-naphthalene disulfonate

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

benzenesulfonic acid

prasugel
150322-43-3

prasugel

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate benzene sulfonate
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;
acetic acid
64-19-7

acetic acid

prasugel
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

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%
maleic acid
110-16-7

maleic acid

prasugel
150322-43-3

prasugel

prasugrel maleate salt
389574-20-3

prasugrel maleate salt

Conditions
ConditionsYield
In acetone at 25 - 30℃; for 3h; Concentration;89.84%
ethane-1,2-disulphonic acid
110-04-3

ethane-1,2-disulphonic acid

prasugel
150322-43-3

prasugel

prasugrel 1,2-ethane disulfonate

prasugrel 1,2-ethane disulfonate

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

prasugel

prasugrel monohydrogensulfate
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%
prasugel
150322-43-3

prasugel

C20H18(2)H2FNO3S

C20H18(2)H2FNO3S

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

prasugel

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

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%
naphthalene-1,5-disulfonate
81-04-9

naphthalene-1,5-disulfonate

prasugel
150322-43-3

prasugel

prasugrel 1,5-naphthalenedisulfonic acid salt

prasugrel 1,5-naphthalenedisulfonic acid salt

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

prasugel

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydroiodide
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%
methanesulfonic acid
75-75-2

methanesulfonic acid

prasugel
150322-43-3

prasugel

prasugrel mesylate salt
1060616-84-3

prasugrel mesylate salt

Conditions
ConditionsYield
In acetone at 20 - 26℃; Cooling;70%
In methanol Product distribution / selectivity;
naphthalene-2-sulfonate
120-18-3

naphthalene-2-sulfonate

prasugel
150322-43-3

prasugel

prasugrel 2-naphthalenesulfonic acid salt
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;
1-naphthalenesulfonic acid
85-47-2

1-naphthalenesulfonic acid

prasugel
150322-43-3

prasugel

prasugrel 1-naphthalenesulfonic acid salt
1178975-73-9

prasugrel 1-naphthalenesulfonic acid salt

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

cyclohexylsulfamic acid

prasugel
150322-43-3

prasugel

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