Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Base Information

• Chemical Name: Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS No.: 140171-66-0
• Molecular Formula: C19H23ClN2O5
• Molecular Weight: 394.855
• UNII: 5TQ5PD1804
• DSSTox Substance ID: DTXSID301111409
• Nikkaji Number: J455.172I
• Wikidata: Q27262859
• Mol file: 140171-66-0.mol

Synonyms:140171-66-0;Amlodipine Dimethyl Ester;Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;Amlodipine besilate impurity F;Amlodipine EP Impurity F;Amlodipine besilate impurity F [EP];UNII-5TQ5PD1804;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3,5-dimethyl ester;5TQ5PD1804;(+/-)-3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, dimethyl ester;2-((2-Aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, dimethyl ester;Dimethyl (4RS)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;Dimethyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester;Dimethyl2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;Amlodipine Besilate Imp. F (EP);Amlodipine Imp. F (EP);Dimethyl (4RS)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;Amlodipine Related Compound F;Amlodipine Besilate Impurity F;Amlodipine Impurity F;Dimetil Amlodipine Analogue;SCHEMBL5477290;rac Methamphetamine Hydrochloride;UDSAEMGNQXMCDF-UHFFFAOYSA-N;DTXSID301111409;2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3,5-dimethyl Ester;AS-78726;FT-0662114;F19443;AMLODIPINE BESILATE IMPURITY F [EP IMPURITY];J-007364;Q27262859;2-Methyl-4-(2-chlorophenyl)-6-[(2-aminoethoxy)methyl]-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester;3,5-Dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate;3-methyl-5-methyl-4-(2-chlorophenyl)-6-methyl-2-[(2-Aminoethoxy)methyl]-1,4-dihydropyridine-3,5-dicarboxylate

Chemical Property of Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Chemical Property:

• Melting Point: 42-45°C
• Boiling Point: 516.6±50.0 °C(Predicted)
• PKA: 8.97±0.10(Predicted)
• PSA: 99.88000
• Density: 1.247±0.06 g/cm3(Predicted)
• LogP: 2.90530
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 394.1295495
• Heavy Atom Count: 27
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

AmlodipineDimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)COCCN)C(=O)OC)C2=CC=CC=C2Cl)C(=O)OC
• Uses: Amlodipine Besilate (A633500) impurity.

Technology Process of Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

There total 6 articles about Dimethyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-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: 84.0%

phthaloyl amlodipine (140171-50-2) → dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate (140171-66-0)

Guidance literature:

With methylamine; In water; at 20 ℃; for 18h;

Reference yield:

N-tritylamlodipine (156366-27-7) + benzenesulfonic acid (98-11-3) → diethyl 2,6-bis[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate (331258-31-2) + dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate (140171-66-0) + amlodipine besylate (111470-99-6)

Guidance literature:

In methanol; for 2h; Heating / reflux;

Reference yield:

acetoacetic acid methyl ester (105-45-3) → dimethyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate (140171-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₃ / ethanol

2: 32 percent / Heating

3: 61 percent / 40percent aq. MeNH₂ / Ambient temperature

With ammonia; methylamine; In ethanol;

DOI:10.1016/0223-5234(91)90132-7

upstream raw materials:

phthaloyl amlodipine

2-chloro-benzaldehyde

methyl 3-aminocrotonate

methyl 4-[2-(phthalimido)-ethoxy]acetoacetate