5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride

Base Information

• Chemical Name: 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride
• CAS No.: 720720-96-7
• Molecular Formula: C8H11ClN2O2S
• Molecular Weight: 234.707
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40456966
• Mol file: 720720-96-7.mol

Synonyms:720720-96-7;5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride;4,5,6,7-TETRAHYDRO-5-METHYL-THIAZOLO[5,4-C]PYRIDINE-2-CARBOXYLIC ACID HCL;5-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride;MFCD25542379;4,5,6,7-tetrahydro-5-methyl-thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride;5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid;hydrochloride;5-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo-[5,4-c]pyridin-2-carboxylic acid hydrochloride;SCHEMBL209036;DTXSID40456966;AMY12276;BCP14308;CS-M3401;AKOS024262565;DS-9377;SB13388;4,5,6,7-tetrahydro-5-methylthiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride;AC-33549;SY097950;FT-0698892;M2819;EN300-7416459;4,5,6,7-tetrahydro-5-methylthiazolo[5,4-c]pyridine-2-carboxylic acid HCl;5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid HCl;5-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-carboxylic acid hydrochloride;5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate hydrochloride;5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride;5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylicacidhydrochloride;Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic Acid Hydrochloride;5-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid--hydrogen chloride (1/1)

Chemical Property of 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride

Chemical Property:

• Melting Point: 199.0 to 203.0 °C
• Boiling Point: 175℃[at 101 325 Pa]
• PSA: 81.67000
• LogP: 1.56910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Very Slig
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 234.0229765
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic Acid Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=C(C1)SC(=N2)C(=O)O.Cl
• Uses: 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic Acid Hydrochloride is used as a reagent in the synthesis of N-(2-acylaminobenzyl or 2-acylaminoheterocyclylmethyl)thiophene-2-carboxamide derivatives as antithrombotics. It is also used as a reagent in the synthesis of diamide derivatives as FXa inhibitors. 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic Acid Hydrochloride is an intermediate for Edoxaban (E555520).

Technology Process of 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride

There total 11 articles about 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride 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: 86.5%

2-bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonate (852291-42-0) + phenyl formate (1864-94-4) → 5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloric acid salt (720720-96-7)

Guidance literature:

2-bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonate; phenyl formate; With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In acetonitrile; at 60 ℃; for 39h; Autoclave; Inert atmosphere;

With lithium hydroxide monohydrate; In tetrahydrofuran; at 20 ℃; for 2h;

With hydrogenchloride; In methanol; at 20 ℃; for 2h; Cooling with ice;

Reference yield: 67.8%

6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid lithium salt → 5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloric acid salt (720720-96-7)

Guidance literature:

6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid lithium salt; With pyrographite; In ethanol; at 40 - 50 ℃; for 0.333333h;

With hydrogenchloride; In water; at 0 - 5 ℃; pH=1 - Ca. 2;

Reference yield:

2-bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonate (852291-42-0) + carbon dioxide (124-38-9,18923-20-1) → 5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloric acid salt (720720-96-7)

Guidance literature:

2-bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonate; With sodium hydroxide; In water; at 20 ℃; for 0.5h;

With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; for 1h; Inert atmosphere;

carbon dioxide; Further stages;

upstream raw materials:

trifluoroacetyl chloride

5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine

carbon dioxide

1-Methyl-4-piperidone

Downstream raw materials:

edoxaban

[14C]-Edoxaban tosylate

N₁-(5-chloropyridin-2-yl)-N₂-{(1S,2S,4R)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid

N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2S,4R)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid

Refernces

• 1、 -. "Preparation method of edoxaban". . . Retrieved 2019/07/08.
• 2、 -. "TRIAMINE DERIVATIVE". Page/Page column 59. . Retrieved 2008/06/13.