2-AMINO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

Base Information

• Chemical Name: 2-AMINO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• CAS No.: 177760-04-2
• Molecular Formula: C7H11N3O2
• Molecular Weight: 169.183
• Hs Code.: 2933290090
• Mol file: 177760-04-2.mol

Synonyms:ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate;2-Amino-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester;2-Amino-1-methyl-1H-imidazole-5-carboxylic acid ethyl ester;2-Amino-5-carbethoxy-1-methyl-imidazol;1-Methyl-2-amino-5-carbethoxyimidazol;1-N-methyl-2-amino imidazole-5-carboxylic acid ethyl ester;

Chemical Property of 2-AMINO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

Chemical Property:

• Boiling Point: 338.2±34.0 °C(Predicted)
• PKA: 5.83±0.25(Predicted)
• PSA: 70.87000
• Density: 1.29
• LogP: 0.10910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%Min ^*data from raw suppliers

ethyl2-amino-1-methyl-1H-imidazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-AMINO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

There total 10 articles about 2-AMINO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL 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: 79.0%

CYANAMID (420-04-2) + sarcosine ethyl ester hydrochloride (52605-49-9) + formic acid ethyl ester (109-94-4) → ethyl 2-amino-1-N-methyl-1H-imidazole-5-carboxylate (177760-04-2)

Guidance literature:

sarcosine ethyl ester hydrochloride; formic acid ethyl ester; With sodium hydride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 18h; Inert atmosphere;

CYANAMID; In tetrahydrofuran; ethanol; at 100 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.chembiol.2021.04.004

Reference yield: 61.0%

ethyl 2-(N-methylformamido)acetate (89531-66-8) → ethyl 2-amino-1-N-methyl-1H-imidazole-5-carboxylate (177760-04-2)

Guidance literature:

ethyl 2-(N-methylformamido)acetate; With sodium hydride; formic acid ethyl ester; sodium nitrite; In tetrahydrofuran; cyclohexane; mineral oil; at 20 ℃; for 3.5h;

With hydrogenchloride; In ethanol; water; at 110 ℃; for 2h;

With CYANAMID; sodium hydroxide; In ethanol; water; for 1.5h; pH=3; Reflux;

DOI:10.1016/j.ejmech.2018.08.060

Reference yield:

CYANAMID (420-04-2) + C7H10NO4(1-)*Na(1+) → ethyl 2-amino-1-N-methyl-1H-imidazole-5-carboxylate (177760-04-2)

Guidance literature:

C₇H₁₀NO₄^(1-)*Na⁽¹⁺⁾; With hydrogenchloride; In ethanol; water; at 20 ℃; for 2h;

CYANAMID; With sodium hydroxide; In ethanol; water; at 100 ℃; for 2h; pH=3;

DOI:10.1016/j.tet.2020.131170

upstream raw materials:

CYANAMID

Methyl formate

sarcosine ethyl ester hydrochloride

ethyl N-formylglycinate

Downstream raw materials:

ethyl 1-N-methyl-2-nitro-1H-imidazole-5-carboxylate

Refernces

• 1、 Calder, Ewen D. D.,Conway, Stuart J.,Folkes, Lisa K.,Hammond, Ester M.,Mistry, Ishna N.,Skwarska, Anna,Sneddon, Deborah. "Hypoxia-activated pro-drugs of the KDAC inhibitor vorinostat (SAHA)". supporting information. . Retrieved 2020/04/24.
• 2、 Winn, Blake A.,Shi, Zhe,Carlson, Graham J.,Wang, Yifan,Nguyen, Benson L.,Kelly, Evan M.,Ross, R. David,Hamel, Ernest,Chaplin, David J.,Trawick, Mary L.,Pinney, Kevin G.. "Bioreductively activatable prodrug conjugates of phenstatin designed to target tumor hypoxia". supporting information. p. 636 - 641. Retrieved 2017/01/17.