115473-15-9

Basic information

• Product Name: Prasugrel
• Synonyms: 5,6,7,7a-Tetrahydro-thieno[3,2-c]pyridin-2(4H)-one Hydrochloride;5,6,7,7a-Tetrahydro-thieno[3,2-c]pyridinone Hydrochloride;5,6,7,7a-Tetrahydrothieno[3,2-c]pyridine-2(4H)-one hydrochloride;2-oxo-2,4,5,6,7,7a-hexahydrothieno [3,2-c] pyridine. Hydrochloride;5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one HCL;2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c];2H,4H,5H,6H,7H,7AH-thieno[3,2-c]pyridin-2-one hydrochloride;5,6,7,7a-Tetrahyhdro-4H-thieno[3,2-c]pyridin-2one.hydrochloride
• CAS NO: 115473-15-9
• Molecular Formula: C₇H₉NOS*ClH
• Molecular Weight: 191.68
• EINECS: 1806241-263-5
• Product Categories: Heterocyclic Compounds;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 115473-15-9.mol

Chemical Properties

• Melting Point: 2100C (dec)
• Boiling Point: 364.3 °C at 760 mmHg
• Flash Point: 174.1 °C
• Appearance: Cream solid
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO, Methanol, Water
• CAS DataBase Reference: Prasugrel(CAS DataBase Reference)
• NIST Chemistry Reference: Prasugrel(115473-15-9)
• EPA Substance Registry System: Prasugrel(115473-15-9)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 115473-15-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Prasugrel is used as an intermediate in the synthesis of Prasugrel (P701150), a medication used to prevent blood clots in patients with a history of heart attack, stroke, or peripheral arterial disease. It is also used as an active pharmaceutical ingredient in the development of new drugs targeting platelet aggregation and clot formation.
Used in Solifenacin Intermediate:
Prasugrel is used as an intermediate in the synthesis of Solifenacin, a medication used to treat overactive bladder and urinary incontinence. It helps to relax the muscles of the bladder and increase the bladder's capacity, reducing the frequency and urgency of urination.

InChI:InChI=1/C7H9NOS.ClH/c9-7-3-5-4-8-2-1-6(5)10-7;/h3,6,8H,1-2,4H2;1H

Synthetic route

5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine (109904-26-9) → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
With hydrogenchloride In water; acetone at 25 - 50℃; for 1h;	99%
With hydrogenchloride In ethanol at 45℃; Solvent; Inert atmosphere;	76%
With hydrogenchloride; water In acetone at 56℃; for 3h;

5-trityl-4,5,6,7-tetrahydro-tieno[3,2-c]pyridine (109904-25-8) → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
Stage #1: N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine With N,N,N,N,-tetramethylethylenediamine; n-hexyllithium In toluene at 0℃; Large scale; Stage #2: With boric acid tributyl ester In toluene at 0℃; for 1h; Large scale; Further stages;	86.1%
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 1.2: 1 h / 0 - 15 °C / Inert atmosphere 1.3: 2 h / 0 - 30 °C 2.1: hydrogenchloride; water / acetone / 3 h / 25 - 30 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 1.2: -5 - 10 °C 2.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 1.2: 1 h / 0 - 15 °C 1.3: 1.75 h / 0 - 30 °C / Reflux 2.1: hydrogenchloride / acetone / 4.5 h / 25 - 30 °C / Reflux View Scheme

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12 - 28 °C 2.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 2.2: -5 - 10 °C 3.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme
Multi-step reaction with 3 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 2.3: 1.75 h / 0 - 30 °C / Reflux 3.1: hydrogenchloride / acetone / 4.5 h / 25 - 30 °C / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / 1,4-dioxane / 0.5 h / 80 °C 1.2: 1 h 2.1: copper dichloride / methanol / 4 h 3.1: methanol / 24 h / Inert atmosphere; Reflux 4.1: hydrogenchloride / methanol / 12 h / 20 °C View Scheme

[2-(2-thyenyl)ethyl]amine (30433-91-1) → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dichloromethane / 40 - 45 °C 1.2: 20 - 70 °C 2.1: triethylamine / dichloromethane / 12 - 28 °C 3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 3.2: -5 - 10 °C 4.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme

6,7-dihydro-4H-thieno[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester (230301-73-2) → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper dichloride / methanol / 4 h 2: methanol / 24 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol / 12 h / 20 °C View Scheme

2-methoxy-5-tert-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine → 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9)

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 12h;	6.5 g

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (150322-38-6)

Conditions	Yield
With ammonium bicarbonate In dichloromethane at 5 - 20℃;	98%
With copper(l) iodide; sodium carbonate; XPhos In 1,4-dioxane at 60℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;	90.2%
With potassium phosphate; iodine In 1,4-dioxane at 80℃; for 4h; Temperature; Time; Reagent/catalyst;	87.6%

+ 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 2-Oxoclopidogrel (1147350-75-1)

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;	70%
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;	70%
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With water; potassium carbonate In dichloromethane for 0.166667h; Stage #2: (R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester In dichloromethane for 6h; Reflux;
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;	18.1 g
With potassium carbonate In acetonitrile at 25 - 35℃; for 12h;	25.4 g

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + (R)-2-(2-chlorophenyl)-2-(4-nitro sulfonyloxy)acetic acid methyl ester-d3 → (2S)-2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridine-5(2H,4H,6H)-yl)acetic acid methyl ester-d3

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;	70%
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;	70%

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4) → (SR)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃;	62%
With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 2h;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + 2-bromo-2-cyclopropyl-1-phenylethan-1-one (84040-29-9) → 5-(α-cyclopropylcarbonylbenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno(3,2-c)pyridine

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 10 - 15℃;	60%

(R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → (S)-(2-chlorophenyl)(2-hydroxy-6,7-dihydro-4H-thiophene[3,2-c]pyridin-5-yl)acetic acid methyl ester (1360591-38-3) + C16H16ClNO3S

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile for 15h; Inert atmosphere;	A 54% B n/a

α-cyclopropylcarbonyl-2-fluorobenzyl chloride (178688-43-2) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (150322-38-6)

Conditions	Yield
With sodium carbonate In acetonitrile at 60℃; for 12h; Inert atmosphere;	52%
With sodium carbonate In acetonitrile at 60℃; for 12h; Molecular sieve; Inert atmosphere;	50%

methyl 2-chloro-2-(2-chlorophenyl)acetate (90055-47-3) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → (SR)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 55℃; for 0.05h; Inert atmosphere; Stage #2: methyl 2-chloro-2-(2-chlorophenyl)acetate In N,N-dimethyl-formamide at 55℃; for 0.166667h; Inert atmosphere;	44%

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + acetic anhydride (108-24-7) → 5-acetyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 5℃; for 1h; Inert atmosphere;	20.03%

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + 2,4-dihydroxy-5- isopropylbenzoic acid (1184181-48-3) → 5-(2,4-dihydroxy-5-isopropylbenzoyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 4h;	10%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + acetic anhydride (108-24-7) → prasugel (150322-43-3)

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 6h; Stage #3: acetic anhydride With triethylamine In acetonitrile at 0 - 30℃; for 6.5h;
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50 - 55℃; for 2h; Stage #2: acetic anhydride In N,N-dimethyl-formamide at 10 - 45℃;

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride (150322-39-7)

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 7h; Stage #3: With hydrogenchloride In ethyl acetate; acetone at 25 - 30℃; for 1h;
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetone; acetonitrile at 25 - 30℃; for 7.5h; Stage #2: With hydrogenchloride In ethyl acetate; acetone at 25 - 30℃; for 1h;

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → CS-747 hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 6.5 h / 0 - 30 °C 2.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → prasugel (150322-43-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °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: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °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: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 0 - 30 °C 2.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 2.2: 6 h / 0 - 5 °C View Scheme

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → CS-747 hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C 3.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °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 4.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 0 - 30 °C 2.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 2.2: 6 h / 0 - 5 °C 3.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 0 - 5 °C View Scheme

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride (150322-39-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C 3.1: ammonia / dichloromethane; water / 0 - 30 °C 3.2: 1 h / 25 - 30 °C View Scheme

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide (1243654-57-0)

Conditions	Yield
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 6h; Stage #3: With hydrogen bromide In water; acetone at 0 - 30℃;
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 10 - 15℃; for 2.5h; Stage #3: With hydrogen bromide In water; acetone at 0 - 30℃; for 3h;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (150322-38-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 20 °C / Inert atmosphere 3: hydrogenchloride; water / ethyl acetate / 20 °C View Scheme

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 20 °C / Inert atmosphere View Scheme

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + tert-butyldimethylsilyl chloride (18162-48-6) → C13H23NOSSi*ClH

Conditions	Yield
With triethylamine In dichloromethane at 28 - 30℃; for 1.75h;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + C15H12FNO7S → 5-(α-methoxycarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c ]pyridine

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + C15H12ClNO7S → (R)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate (1360923-54-1)

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + (R)-methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)-acetate → (SR)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere;

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + methyl 2-phenyl-2-(((p-nitrophenyl)sulfonyl)oxy)acetate (142026-00-4, 87119-37-7) → Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate (109904-28-1)

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 20℃;

Upstream product

• 109904-26-9 5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 109904-25-8 N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 
• 230301-73-2 6,7-dihydro-4H-thieno[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester 

Downstream Products

• 150322-43-3 prasugel 
• 150322-39-7 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride 
• 150322-38-6 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one 
• 952340-38-4 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1391194-39-0 5-(2-cyclopropyl-1-(3-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno [3,2-c]pyridin-2-yl acetate 
• 1443034-67-0 5-(1-(2-fluorophenyl)-2-oxopropyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate 
• 1391194-45-8 5-(2-cyclopropyl-2-oxo-1-phenylethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate 
• 1346456-13-0 C₁₅H₁₄N₂OS 
• 1346456-11-8 C₁₅H₁₄N₂OS 
• 1346456-06-1 (5-(2-cyanobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)acetate taurate 
• 1346456-05-0 (5-(2-cyanobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)acetate hydrochloride 
• 1346456-04-9 (5-(4-cyanobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)acetate 
• 1346456-03-8 (5-(3-cyanobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)acetate 
• 1346456-01-6 (5-(2-cyanophenmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-yl) acetate 

Relevant articles and documents

A method for preparing prasugrel intermediate

The invention provides a preparation method of a Prasugrel intermediate. The method comprises the following steps: performing an amino protection reaction by taking 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride as a raw material; and performing a halogenating reaction, an alkylation reaction, a sodium alkoxide deprotection reaction and an HCl gas acidifying reaction to obtain a target compound. The method is simple, advanced in process, small in the quantity of three wastes produced in a production process, low in environmental protection stress, high in yield, and suitable for industrial production.

PROCESS FOR THE PREPARATION OF HIGH-PURITY PRASUGREL

The field of invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of high-purity 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7- tetrahydrothieno[3,2-c]pyridine-2-yl acetate, prasugrel, of Formula (I). Especially in large-scale production, one of the main causes of piling up the impurities is the use of ether solvents consequently in each step in this procedure ethers are excluded. Avoiding the ethers resulted new conditions for production of intermediates in the different steps of our procedure. Conditions were determined so that each step from the beginning contributes to minimizing the impurity content of the end-product.

Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development

Clopidogrel is a prodrug anticoagulant with active metabolites that irreversibly inhibit the platelet surface GPCR P2Y12 and thus inhibit platelet activation. However, gaining an understanding of patient response has been limited due to imprecise understanding of metabolite activity and stereochemistry, and a lack of acceptable analytes for quantifying in vivo metabolite formation. Methods for the production of all bioactive metabolites of clopidogrel, their stereochemical assignment, and the development of stable analytes via three conceptually orthogonal routes are disclosed. (Chemical Equation Presented).

AN IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL HYDROCHLORIDE AND ITS INTERMEDIATES

The present invention provides an improved process for the preparation of prasugrel and its pharmaceutical acceptable salt. Prasugrel chemically known as 2-acetoxy-5-(a- cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine or 5-[2- cyclopropyl-l-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2,-c]pyridine- 2yl acetate and having the structural formula (I) and its pharmaceutically acceptable salts. The present invention also provides an improved process for the preparation of cyclopropyl 2-fluorobenzyl ketone, 2-Fluoro-a-cyclopropyl carbonylbenzyl bromide, 5,6,7,7a Tetrahydro-4H- theino-[3,2-c]- pyridone-2 p-toluenesulfonate and its hydrochloride salt.

Processes For Preparing Prasugrel And Pharmaceutically Acceptable Salts Thereof

Disclosed are improved processes for preparing prasugrel compound of formula-(1), its intermediates and pharmaceutically acceptable salts.

NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF PRASUGREL, ITS INTERMEDIATES AND PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to novel and improved processes for the preparation of prasugrel compound of formula-(1), its intermediates and pharmaceutically acceptable salts.

PHARMACEUTICAL COMPOSITION OF PRASUGREL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to a pharmaceutical composition of prasugrel or its pharmaceutically acceptable salts thereof as well as process for its preparation. Formula (I).

A PROCESS FOR THE PREPARATION OF PRASUGREL HCL SALT

The present invention relates to process for the preparation of Prasugrel HCl having formula (I).

PROCESSES FOR THE PREPARATION OF PRASUGREL, AND ITS SALTS AND POLYMORPHS

Processes for the preparation of prasugrel and its pharmaceutically acceptable salts thereof. Also disclosed are polymorphic forms of prasugrel hydrochloride and processes for their preparation.