3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester

Base Information

• Chemical Name: 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester
• CAS No.: 133147-19-0
• Molecular Formula: C₂₂H₂₇N₃O₆
• Molecular Weight: 429.473
• DSSTox Substance ID: DTXSID90927974
• Mol file: 133147-19-0.mol

Synonyms:BRN 4277878;133147-19-0;3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester;DTXSID90927974;LS-130841;Methyl 5-[(cyclopentyloxy)(methyl)carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

Chemical Property of 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester

Chemical Property:

• Vapor Pressure: 6.87E-12mmHg at 25°C
• Boiling Point: 543.9°C at 760 mmHg
• Flash Point: 282.7°C
• Density: 1.29g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 429.18998559
• Heavy Atom Count: 31
• Complexity: 794

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)N(C)OC3CCCC3

Technology Process of 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester

There total 4 articles about 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-(((cyclopentyloxy)methylamino)carbonyl)-4-(3-nitrophenyl)-, methyl ester 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: 76.0%

(E)-3-Amino-but-2-enoic acid cyclopentyloxy-methyl-amide (133147-05-4) + methyl 2-E,Z-(3-nitro-phenylmethylen)-3-oxobutanoate (118431-03-1) → 5-(Cyclopentyloxy-methyl-carbamoyl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester (133147-19-0)

Guidance literature:

In ethanol; for 5h; Heating;

Reference yield:

N-methyl-N-cyclopentyloxyurethane (133146-78-8) → 5-(Cyclopentyloxy-methyl-carbamoyl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester (133147-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / 30percent HCl / Heating

2: 39 percent / NEt₃ / toluene; methanol / 0.5 h / 0 - 5 °C

3: 76 percent / methanol / 8 h / Ambient temperature

4: 76 percent / ethanol / 5 h / Heating

With hydrogenchloride; triethylamine; In methanol; ethanol; toluene;

Reference yield:

N-methyl-O-cyclopentylhydroxylamine hydrochloride → 5-(Cyclopentyloxy-methyl-carbamoyl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester (133147-19-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 39 percent / NEt₃ / toluene; methanol / 0.5 h / 0 - 5 °C

2: 76 percent / methanol / 8 h / Ambient temperature

3: 76 percent / ethanol / 5 h / Heating

With triethylamine; In methanol; ethanol; toluene;

upstream raw materials:

(E)-3-Amino-but-2-enoic acid cyclopentyloxy-methyl-amide

methyl 2-E,Z-(3-nitro-phenylmethylen)-3-oxobutanoate

N-methyl-N-cyclopentyloxyurethane

N-Cyclopentyloxy-N-methyl-3-oxo-butyramide