(R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide

Base Information

• Chemical Name: (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide
• CAS No.: 1681056-61-0
• Molecular Formula: C₂₈H₂₅N₃O₆S₂
• Molecular Weight: 563.655

Synonyms:

Chemical Property of (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide

Chemical Property:

• Density: 1.389±0.06 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

OSMI1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: OSMI 1 is a novel inhibitor of O-GlcNAc transferase (OGT). OSMI-1 (OGT with a small molecule inhibitor) has been used in proximal ligation assay, Sox2 (SRY (sex determining region Y)-Box 2 ) dual luciferase reporter assay, Sox2 ELISA (enzyme linked immunosorbent assay) and other in vivo approaches, to study the O-Linked β-N-acetylglucosamine (O-GlcNAc) mediated regulation of self-renewal genes in cancer. It has also been used to study the Hippo pathway regulation mediated by O-GlcNAc transferase.

Technology Process of (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide

There total 5 articles about (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide 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: 56.0%

2-oxo-1,2-dihydro-6-quinolinesulfonyl chloride (569340-07-4) + (R)-tert-butyl (2-((furan-2-ylmethyl)(thiophen-2-ylmethyl)amino)-1-(2-methoxyphenyl)-2-oxoethyl)carbamate → (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide (1681056-61-0)

Guidance literature:

(R)-tert-butyl (2-((furan-2-ylmethyl)(thiophen-2-ylmethyl)amino)-1-(2-methoxyphenyl)-2-oxoethyl)carbamate; With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 1.5h;

2-oxo-1,2-dihydro-6-quinolinesulfonyl chloride; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 23 ℃; for 14h;

Reference yield:

2-quinolone (59-31-4,70254-42-1,493-62-9) → (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide (1681056-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chlorosulfonic acid / 3 h / 90 °C

2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 23 °C

2.2: 14 h / 23 °C

With chlorosulfonic acid; trifluoroacetic acid; In dichloromethane;

Reference yield:

furan-2-ylmethanamine (617-89-0) → (R)-N-(furan-2-ylmethyl)-2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamide (1681056-61-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ethanol / 0.5 h / 120 °C / Microwave irradiation

1.2: 19 h / 23 - 90 °C

2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 23 °C

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 23 °C

3.2: 14 h / 23 °C

With N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2-oxo-1,2-dihydro-6-quinolinesulfonyl chloride

2-quinolone

furan-2-ylmethanamine

thiophene-2-carbaldehyde

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