3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate

Base Information

• Chemical Name: 3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate
• CAS No.: 113994-41-5
• Molecular Formula: C20H23 Cl N2 O5
• Molecular Weight: 406.866
• Hs Code.: 2933399090
• European Community (EC) Number: 642-062-7
• UNII: 38Q8451QLU
• DSSTox Substance ID: DTXSID70150622
• Nikkaji Number: J1.658.639K
• Wikidata: Q27256805
• Mol file: 113994-41-5.mol

Synonyms:113994-41-5;3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate;Amlodipine besilate impurity D;Amlodipine EP Impurity D;Amlodipine impurity A;3-ETHYL 5-METHYL 2-[(2-AMINOETHOXY)METHYL]-4-(2-CHLOROPHENYL)-6-METHYLPYRIDINE-3,5-DICARBOXYLATE;UK 55-410;UK-55-410;38Q8451QLU;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-, 3-ethyl 5-methyl ester;Dehydro Amlodipine;UNII-38Q8451QLU;Amlodipine besilate impurity D [EP];DEHYDROAMLODIPINE;Amlodipine metabolite M9;3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate;C20H23ClN2O5;SCHEMBL4632845;DTXSID70150622;AKOS022179614;Dehydro amlodipine(amlodipine impurity d);EN300-740172;F19499;A894287;AMLODIPINE BESILATE IMPURITY D [EP IMPURITY];Q27256805;Z3177423114;3-Ethyl5-methyl2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate

Chemical Property of 3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate

Chemical Property:

• Melting Point: 106-108°C
• Boiling Point: 517.9±50.0 °C(Predicted)
• PKA: 8.42±0.10(Predicted)
• PSA: 100.74000
• Density: 1.241±0.06 g/cm3(Predicted)
• LogP: 3.84930
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 406.1295495
• Heavy Atom Count: 28
• Complexity: 521

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dehydro Amlodipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(N=C1COCCN)C)C(=O)OC)C2=CC=CC=C2Cl
• Uses: Amlodipine impurity D Dehydro Amlodipine is an Amlodipine (A633495) impurity. Dehydro Amlodipine (Amlodipine Besylate EP Impurity D) is an Amlodipine (A633495) impurity.

Technology Process of 3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate

There total 8 articles about 3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate 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: 98.0%

2-[2-(phthalimido)ethoxymethyl]-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-methylpyridine → 2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester (113994-41-5)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 20h;

DOI:10.3987/COM-04-10194

Reference yield: 93.4%

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (103129-81-3) → 2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester (113994-41-5)

Guidance literature:

With calcium hypochlorite; In water; ethyl acetate; at 20 - 30 ℃; Reagent/catalyst; Temperature; Solvent;

Reference yield: 73.2%

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9) → 2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester (113994-41-5)

Guidance literature:

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine; With hydrogenchloride; In water;

With nickel; In water; at 20 ℃; for 6h;

upstream raw materials:

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

amlodipine

(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

Downstream raw materials:

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester; compound with (E)-but-2-enedioic acid

Refernces

• 1、 Zhu, Yanlin,Wang, Fen,Li, Quan,Zhu, Mingshe,Du, Alicia,Tang, Wei,Chen, Weiqing. "Amlodipine metabolism in human liver microsomes and roles of CYP3A4/5 in the dihydropyridine dehydrogenation". . p. 245 - 249. Retrieved 2014.
• 2、 -. "Method for preparing levamlodipine". Paragraph 0044-0056. . Retrieved 2020/10/14.