28783-38-2

Basic information

• Product Name: 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE
• Synonyms: 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE;4,5,67-tetrehydrothieno[2,3-c]pyridine hydrochloride;7-tetrahydrothieno[2;4,5,6,7-Tetrahydrothieno[2,3-c]pyridine, HCl;4,5,6,7-tetrahydrothieno[2,3-c]pyridin-6-iuM chloride;Thieno[2,3-c]pyridine,4,5,6,7-tetrahydro-, hydrochloride (1:1);4H,5H,6H,7H-thieno[2,3-c]pyridine hydrochloride
• CAS NO: 28783-38-2
• Molecular Formula: C₇H₉NS*ClH
• Molecular Weight: 175.68
• Product Categories: API intermediates;CHIRAL CHEMICALS;Building Blocks;Thieno[x,x-y]pyridine;Bases & Related Reagents;Heterocycles;Nucleotides;Sulfur & Selenium Compounds;Heterocycle-Pyridine series
• Mol File: 28783-38-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 278.3 °C at 760 mmHg
• Flash Point: 122.1 °C
• Appearance: /
• Vapor Pressure: 0.00331mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO, Methanol
• CAS DataBase Reference: 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE(28783-38-2)
• EPA Substance Registry System: 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE(28783-38-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 28783-38-2(Hazardous Substances Data)

Usage

Description

4,5,6,7-Tetrahydrothieno[2,3-c]pyridine hydrochloride is an organic compound with a chemical structure that features a thieno-tetrahydropyridine ring. It is a white solid and is known for its potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
4,5,6,7-Tetrahydrothieno[2,3-c]pyridine hydrochloride is used as a key intermediate compound for the preparation of thieno-tetrahydropyridines. These thieno-tetrahydropyridines are valuable as class III antiarrhythmic agents, which are medications that help regulate abnormal heart rhythms. 4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE HYDROCHLORIDE's chemical properties make it a suitable candidate for the development of these life-saving drugs.

InChI:InChI=1/C7H9NS.ClH/c1-3-8-5-7-6(1)2-4-9-7;/h2,4,8H,1,3,5H2;1H

Synthetic route

6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-6H-thieno[2,3-c]pyridine (165947-52-4) → 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2)

Conditions	Yield
With hydrogenchloride In methanol

di-tert-butyl dicarbonate (24424-99-5) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-6H-thieno[2,3-c]pyridine (165947-52-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4.5h;	100%

4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 2-bromo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide

Conditions	Yield
With bromine In acetic acid at 20℃; for 1.5h;	90%

4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) + (S)-1-phenyl-2-(tosyloxy)ethanol (40435-14-1) → (S)-2-(4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)-1-phenylethanol

Conditions	Yield
With triethylamine at 80℃; for 4h;	90%

di-tert-butyl dicarbonate (24424-99-5) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Conditions	Yield
With triethylamine; dmap In ethyl acetate; N,N-dimethyl-formamide	88%

3-[4-[[4-(bromomethyl)phenyl]methoxy]-1-oxo-isoindolin-2-yl]piperidine-2,6-dione (1323407-86-8) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 3-{4-[4-(4,7-Dihydro-5H-thieno[2,3-c]pyridin-6-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione (1323403-95-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	74%

(R)-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decane-9-yl)acetaldehyde (1401031-28-4) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → (R)-6-(2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Conditions	Yield
Stage #1: 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde; 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride With sodium sulfate In dichloromethane at 20℃; Stage #2: With sodium tetrahydroborate In dichloromethane for 0.5h;	10%

diethyl cyanophosphonate (2942-58-7) + 6-phenylhexanic acid (5581-75-9) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 1-(5,7-dihydro-4H-thieno[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

Conditions	Yield
With triethylamine In dichloromethane

4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → 2-bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (1200131-56-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / acetic acid / 1.5 h / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran / 0 - 60 °C View Scheme

methyl (R)-2-(2-chlorophenyl)-2-benzenesulfonyloxyacetate (223123-46-4) + 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (28783-38-2) → (S)-(+)-clopidogrel (113665-84-2)

Conditions	Yield
With potassium carbonate at 25 - 40℃; for 24h; Temperature;

Upstream product

• 165947-52-4 6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-6H-thieno[2,3-c]pyridine 

Downstream Products

• 1423033-44-6 2-bromo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide 
• 165947-52-4 6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydro-6H-thieno[2,3-c]pyridine 
• 113665-84-2 (S)-(+)-clopidogrel 

Relevant articles and documents

Condensed compounds, their production and use

This invention provides new condensed furan compounds which exhibit excellent 2,3-oxidosqualene cyclase inhibition and high-density lipoprotein-cholesterol elevating activities. This invention also provides a therapeutic and prophylactic agent for hyperlipidemia, hypercholesterolemia and atherosclerosis.