4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

Base Information

• Chemical Name: 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid
• CAS No.: 107754-20-1
• Molecular Formula: C24H26 N2 O5
• Molecular Weight: 422.481
• UNII: UEM3BGH9XB
• ChEMBL ID: CHEMBL298727
• DSSTox Substance ID: DTXSID20461477
• Nikkaji Number: J322.304C
• Wikidata: Q82285836
• Mol file: 107754-20-1.mol

Synonyms:107754-20-1;4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid;4-[[5-[[(CYCLOPENTYLOXY)CARBONYL]AMINO]-1-METHYL-1H-INDOL-3-YL]METHYL]-3-METHOXYBENZOIC ACID;UEM3BGH9XB;UNII-UEM3BGH9XB;4-[[5-(cyclopentyloxycarbonylamino)-1-methylindol-3-yl]methyl]-3-methoxybenzoic acid;CHEMBL298727;Benzoic acid, 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxy-;KFQBKNCZRCRBOU-UHFFFAOYSA-N;4-[[5-[[cyclopentyloxy)carbonyl]amino]-1-methylindol-3-yl]methyl]-3-methoxybenzoic acid;SCHEMBL4154643;DTXSID20461477;BDBM50015529;AKOS015900897;4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid;FT-0665385;{3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester;4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid;4-(5-cyclopentyloxycarbonylamino-1-methylindol-3-ylmethyl)-3-methoxybenzoic acid;4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic acid;4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3ylmethyl]-3-methoxybenzoic acid;4-[[5-[[(cyclopentyloxy)carbonyl]amino]-1-methyl-1h-indol-3-yl]methyl]-3-methoxy-benzoic acid

Chemical Property of 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

Chemical Property:

• Vapor Pressure: 2.58E-15mmHg at 25°C
• Melting Point: 203-209?C (dec.)
• Refractive Index: 1.629
• Boiling Point: 601.4°C at 760 mmHg
• Flash Point: 317.5°C
• PSA: 93.28000
• Density: 1.3g/cm³
• LogP: 4.98060
• Storage Temp.: Refrigerator
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 422.18417193
• Heavy Atom Count: 31
• Complexity: 638

Purity/Quality:

98%min ^*data from raw suppliers

4-[[5-[[(Cyclopentyloxy)carbonyl]amino]-1-methyl-1H-indol-3-yl]methyl]-3-methoxybenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=C1C=CC(=C2)NC(=O)OC3CCCC3)CC4=C(C=C(C=C4)C(=O)O)OC
• Uses: An intermediate of Zafirlukast (Z125000), as leukotriene antagonist.

Technology Process of 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

There total 10 articles about 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid 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: 98.2%

methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methyl-indol-3-ylmethyl]-3-methoxybenzoate (107754-19-8) → 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid (107754-20-1)

Guidance literature:

With lithium hydrochloride monohydrate; In methanol; water; Reflux; Large scale reaction;

DOI:10.1021/op800137b

Reference yield:

methyl 4-methyl-3-methoxybenzoate (3556-83-0) → 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid (107754-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / Reflux; Inert atmosphere

2: iron(III) chloride / 1,4-dioxane / 12 h / 20 °C / Inert atmosphere

3: hydrogen; palladium on activated charcoal / 12 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 4 - 20 °C / Inert atmosphere

5: lithium hydroxide / water; methanol / 16 h / 20 °C / Inert atmosphere

With iron(III) chloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; water; 2: |Friedel-Crafts Alkylation;

DOI:10.1021/acs.jmedchem.8b00458

Reference yield:

methyl 4-(bromomethyl)-3-methoxybenzoate (70264-94-7) → 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid (107754-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C

2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min

3: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr

4: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

5: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h

With 4-methyl-morpholine; lithium hydroxide; hydrogen; sodium hydride; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jm00168a037

upstream raw materials:

methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methyl-indol-3-ylmethyl]-3-methoxybenzoate

cyclopentyl chloroformate

methyl 4-(bromomethyl)-3-methoxybenzoate

methyl 4-<(5-amino-1-methylindol-3-yl)methyl>-3-methoxybenzoate