Deschloro ticlopidine

Base Information

• Chemical Name: Deschloro ticlopidine
• CAS No.: 55142-78-4
• Molecular Formula: C14H15NS
• Molecular Weight: 229.346
• UNII: 5M52XJ51O8
• DSSTox Substance ID: DTXSID90203649
• Wikidata: Q27262540
• Mol file: 55142-78-4.mol

Synonyms:Deschloro ticlopidine;55142-78-4;Ticlopidine Impurity D;5-benzyl-6,7-dihydro-4H-thieno[3,2-c]pyridine;UNII-5M52XJ51O8;5M52XJ51O8;5-Benzyl-4,5,6,7-tetrahydrothieno(3,2-C)pyridine;Ticlopidine hydrochloride impurity D [EP];Thieno(3,2-C)pyridine, 4,5,6,7-tetrahydro-5-(phenylmethyl)-;5-Benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine;5-benzyl-4H,5H,6H,7H-thieno[3,2-c]pyridine;SCHEMBL2930573;DTXSID90203649;AKOS027343577;5-benzyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine;Q27262540;TICLOPIDINE HYDROCHLORIDE IMPURITY D [EP IMPURITY]

Chemical Property of Deschloro ticlopidine

Chemical Property:

• Melting Point: 239-241 °C
• Boiling Point: 339.2±37.0 °C(Predicted)
• PKA: 7.53±0.20(Predicted)
• PSA: 31.48000
• Density: 1.175±0.06 g/cm3(Predicted)
• LogP: 3.24430
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 229.09252066
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

99%,98%, ^*data from raw suppliers

DeschloroTiclopidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC2=C1SC=C2)CC3=CC=CC=C3
• Uses: Deschloro Ticlopidine is an impurity of Ticlopidine (T438325), an antithrombotic. A platelet aggregation inhibitor.

Technology Process of Deschloro ticlopidine

There total 6 articles about Deschloro ticlopidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) + benzyl chloride (100-44-7) → 5-benzyl-4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine (55142-78-4)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In acetonitrile; at 70 ℃;

DOI:10.1016/j.tetlet.2012.07.071

Reference yield: 85.0%

5-Benzyl-hexahydro-thieno[3,2-c]pyridine-3,7a-diol (137935-57-0) → 5-benzyl-4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine (55142-78-4)

Guidance literature:

With sulfuric acid; at 60 ℃; for 4h;

Reference yield: 59.0%

4,5,6,7-tetrahydrothieno[3,2-c]pyridine (54903-50-3) + benzyl bromide (100-39-0) → 5-benzyl-4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine (55142-78-4)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1021/acs.joc.8b03238

upstream raw materials:

thieno[3,2-c]pyridine

benzyl chloride

5-Benzyl-hexahydro-thieno[3,2-c]pyridine-3,7a-diol

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

Downstream raw materials:

prasugel

2-(2-fluorophenyl)-2-(2-methoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetonitrile

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

C₁₈H₁₈FNO₂S

Refernces

• 1、 -. "A process for the preparation of the new process prasugrel hydrochloride". Paragraph 009; 0019; 0020. . Retrieved 2018/09/02.
• 2、 Gooding, Owen W.,Beard, Colin C.. "USE OF MERCAPTOACETALDEHYDE DIMER IN A NOVEL THIENOANNELATION SEQUENCE. A SHORT SYNTHESIS OF TICLOPIDINE". . p. 1777 - 1780. Retrieved 2007/10/02.