N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt

Base Information

• Chemical Name: N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt
• CAS No.: 1239034-62-8
• Molecular Formula: C₂HF₃O₂*C₂₀H₂₁N₃O₂
• Molecular Weight: 449.43
• Mol file: 1239034-62-8.mol

Synonyms:N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt

Chemical Property of N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt

There total 9 articles about N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt 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: 15.0%

4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester (1239034-71-9) + trifluoroacetic acid (76-05-1) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt (1239034-62-8)

Guidance literature:

4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester; With hydroxylamine hydrochloride; sodium methylate; In methanol; N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm200773h

Reference yield:

tetrahydrobetacarboline (16502-01-5) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt (1239034-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium cyanoborohydride / water; methanol / 2 h

1.2: 0.25 h

1.3: pH 11

2.1: potassium tert-butylate / dimethyl sulfoxide / 0.33 h / 120 °C / Inert atmosphere

2.2: 3 h / 120 °C / Inert atmosphere

3.1: hydroxylamine hydrochloride; sodium methylate / methanol / 24 h / 20 °C / Inert atmosphere

3.2: HPLC column

With hydroxylamine hydrochloride; potassium tert-butylate; sodium methylate; sodium cyanoborohydride; In methanol; water; dimethyl sulfoxide;

Reference yield:

N-hydroxy-4-((1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-9-yl)methyl)benzamide trifluoroacetate (1354547-65-1) + trifluoroacetic acid (76-05-1) + methyl iodide (74-88-4) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt (1239034-62-8)

Guidance literature:

N-hydroxy-4-((1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-9-yl)methyl)benzamide trifluoroacetate; methyl iodide; With triethylamine; In acetonitrile; at 60 ℃; for 16h;

trifluoroacetic acid;

DOI:10.1021/acs.jmedchem.8b01936

upstream raw materials:

N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide

trifluoroacetic acid

4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester

tetrahydrobetacarboline

Refernces

• 1、 Kalin, Jay H.,Butler, Kyle V.,Akimova, Tatiana,Hancock, Wayne W.,Kozikowski, Alan P.. "Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells". experimental part. p. 639 - 651. Retrieved 2012/03/11.
• 2、 Butler, Kyle V.,Kalin, Jay,Brochier, Camille,Vistoli, Guilio,Langley, Brett,Kozikowski, Alan P.. "Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A". supporting information; experimental part. p. 10842 - 10846. Retrieved 2010/09/16.