2-[(CARBOXYCARBONYL)AMINO]-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE

Base Information

• Chemical Name: 2-[(CARBOXYCARBONYL)AMINO]-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE
• CAS No.: 243967-42-2
• Molecular Formula: C10H10N2O5S
• Molecular Weight: 306.72300
• Mol file: 243967-42-2.mol

Synonyms:TCS 401;

Chemical Property of 2-[(CARBOXYCARBONYL)AMINO]-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE

Chemical Property:

• PSA: 143.97000
• LogP: 1.31890
• Storage Temp.: Desiccate at RT

Purity/Quality:

99% ^*data from raw suppliers

TCS 401 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(CARBOXYCARBONYL)AMINO]-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE

There total 4 articles about 2-[(CARBOXYCARBONYL)AMINO]-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-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: 88.0%

2-(tert-butoxyoxalylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester (474843-70-4) → 2-(oxalylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid (243967-42-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/jm0209026

Reference yield: 81.0%

monomethyl oxalyl chloride (5781-53-3) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + cyanoacetic acid (372-09-8) → 2-(oxalylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid (243967-42-2)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)01470-8

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 2-(oxalylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid (243967-42-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / sulfur; morpholine / ethanol / 1 h / 50 °C

2: 68 percent / TEA / CH₂Cl₂ / 16 h / 20 °C

3: 88 percent / TFA / CH₂Cl₂ / 16 h / 20 °C

With morpholine; TEA; sulfur; trifluoroacetic acid; In ethanol; dichloromethane; 1: Gewald's 2-aminothiophene reaction;

DOI:10.1021/jm0209026

upstream raw materials:

monomethyl oxalyl chloride

N-tert-butyloxycarbonylpiperidin-4-one

cyanoacetic acid

2-(tert-butoxyoxalylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

Refernces

• 1、 Andersen, Henrik Sune,Olsen, Ole H.,Iversen, Lars F.,S?rensen, Anette L. P.,Mortensen, Steen B.,Christensen, Michael S.,Branner, Sven,Hansen, Thomas K.,Lau, Jesper F.,Jeppesen, Lone,Moran, Edmond J.,Su, Jing,Bakir, Farid,Judge, Luke,Shahbaz, Manou,Collins, Tassie,Vo, Todd,Newman, Michael J.,Ripka, William C.,M?ller, Niels Peter H.. "Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B". . p. 4443 - 4459. Retrieved 2007/10/03.