2-[(5-Amino-4-carbamoylimidazol-1-YL)methoxy]ethyl acetate

Base Information

• Chemical Name: 2-[(5-Amino-4-carbamoylimidazol-1-YL)methoxy]ethyl acetate
• CAS No.: 118966-30-6
• Molecular Formula: C9H14 N4 O4
• Molecular Weight: 242.23186
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID50555252
• Wikidata: Q82436550
• Mol file: 118966-30-6.mol

Synonyms:118966-30-6;2-[(5-AMINO-4-CARBAMOYLIMIDAZOL-1-YL)METHOXY]ETHYL ACETATE;ACETIC ACID 2-(5-AMINO-4-CARBAMOYL-IMIDAZOL-1-YLMETHOXY)-ETHYL ESTER;2-[(5-Amino-4-carbamoyl-1H-imidazol-1-yl)methoxy]ethyl acetate;SCOKPTHVGOEBIW-UHFFFAOYSA-N;SCHEMBL9363532;DTXSID50555252;5-Amino-1-[[2-(acetyloxy)ethoxy]methyl]-1H-imidazole-4-carboxamide

Chemical Property of 2-[(5-Amino-4-carbamoylimidazol-1-YL)methoxy]ethyl acetate

Chemical Property:

• PSA: 123.45000
• LogP: 0.56680
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 242.10150494
• Heavy Atom Count: 17
• Complexity: 286

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCCOCN1C=NC(=C1N)C(=O)N

Technology Process of 2-[(5-Amino-4-carbamoylimidazol-1-YL)methoxy]ethyl acetate

There total 1 articles about 2-[(5-Amino-4-carbamoylimidazol-1-YL)methoxy]ethyl acetate 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:

1-acetoxy-2-chloromethoxyethane (40510-88-1) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide (118966-30-6)

Guidance literature:

With potassium hydroxide; Yield given. Multistep reaction; 1) DMF, 5 h, ice bath, 2) 0-8 deg C, 0.5 h;

DOI:10.1021/jo00006a033

Reference yield:

5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide (118966-30-6) + Benzoyl isothiocyanate (532-55-8) → acetic acid 2-[5-(3-benzoyl-thioureido)-4-carbamoyl-imidazol-1-ylmethoxy]-ethyl ester

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ja0389523

Reference yield:

5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide (118966-30-6) → 9-(2-hydroxyethoxy)methyl-2-phenylaminopurine (118966-38-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / p-TsCl / pyridine / Ambient temperature

2: 78 percent / dimethylformamide / 3 h / 50 °C

3: 83 percent / 1N NaOH / H₂O / 0.5 h / 50 °C

4: 61 percent / Raney Ni / ethanol / 2 h / Heating

With sodium hydroxide; nickel; p-toluenesulfonyl chloride; In pyridine; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

1-acetoxy-2-chloromethoxyethane

5-amino-1H-imidazole-4-carboxamide monohydrochloride

Downstream raw materials:

9-(2-hydroxyethoxy)methyl-2-phenylaminopurine

9-(2-hydroxyethoxy)methyl-2-phenylamino-6-thioxopurine

9-(2-hydroxyethoxy)methyl-2-phenylamino-6-methylthiopurine

3-(2-acetoxyethoxy)methyl-5-phenylamino-7-(N-phenylthiocarbamoyl)iminoimidazo<4,5-d><1,3>thiazine

Refernces