5-Aminoimidazole-4-carboxamide

Base Information

• Chemical Name: 5-Aminoimidazole-4-carboxamide
• CAS No.: 360-97-4
• Deprecated CAS: 932-15-0
• Molecular Formula: C4H6N4O
• Molecular Weight: 126.118
• Hs Code.: 29332900
• European Community (EC) Number: 206-641-4
• NSC Number: 7784
• UNII: 3V0Y2PDE6K
• DSSTox Substance ID: DTXSID8059891
• Nikkaji Number: J37.792I
• Wikidata: Q27067435
• Metabolomics Workbench ID: 38266
• ChEMBL ID: CHEMBL1610
• Mol file: 360-97-4.mol

Synonyms:Aminoimidazole Carboxamide;Ba 2756;Carboxamide, Aminoimidazole

Chemical Property of 5-Aminoimidazole-4-carboxamide

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Vapor Pressure: 2.59E-10mmHg at 25°C
• Melting Point: 164-170 °C(lit.)
• Refractive Index: 1.673
• Boiling Point: 522.1 °C at 760 mmHg
• PKA: 11.97±0.10(Predicted)
• Flash Point: 269.6 °C
• PSA: 97.79000
• Density: 1.538 g/cm³
• LogP: 0.37230
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in DMSO, Methanol, Water.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 126.05416083
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

5-Aminoimidazole-4-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1)C(=O)N)N
• Recent ClinicalTrials: A Trial to Evaluate Two Schedules of MS275 in Combination With 5AC in Elderly Patients With Acute Myeloid Leukemia (AML)
• Description: 5-Amino-4-imidazolecarboxamide may be used in the synthesis of 4-(N′-benzoylcarbamoyl)amino-5-imidazolecarboxamide and 5-amino-1-β-D-ribosyl-4-imidazolecarboxamide-5′-phosphate (AICAR).It is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. When compounded with orotic acid, it is used to treat liver diseases.
• Uses: A metabolite of Temozolomide 4-Aminoimidazole-5-carboxamide is used as Catalytic agent, Petrochemical additive. It is metabolite of temozolomide. 5-Amino-4-imidazolecarboxamide may be used in the synthesis of 4-(N′-benzoylcarbamoyl)amino-5-imidazolecarboxamide and 5-amino-1-β-D-ribosyl-4-imidazolecarboxamide-5′-phosphate (AICAR).

Technology Process of 5-Aminoimidazole-4-carboxamide

There total 26 articles about 5-Aminoimidazole-4-carboxamide 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: 68.2%

CYANAMID (420-04-2) + isocyanoacetamide (51641-98-6) → 5-Aminoimidazole-4-carboxamide (360-97-4)

Guidance literature:

isocyanoacetamide; With sodium hydride; In tetrahydrofuran; for 0.5h; Cooling with ice; Inert atmosphere;

CYANAMID; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere; Cooling with ice;

Reference yield: 67.5%

hypoxanthine (68-94-0) → 5-Aminoimidazole-4-carboxamide (360-97-4)

Guidance literature:

With ammonia; In water; at 125 ℃; for 65h; under 9880.66 - 10640.7 Torr; Reagent/catalyst; Temperature; Time; Autoclave; Inert atmosphere;

DOI:10.1021/acs.oprd.1c00013

Reference yield: 24.0%

5-amino-N'-ethylimidazole-4-carboxamidine → 5-Aminoimidazole-4-carboxamide (360-97-4) + 5-amino-N-ethylimidazole-4-carboxamide (7253-70-5)

Guidance literature:

With water; at 100 ℃; for 336h; pH 7 (KH₂PO₄-Na₂HPO₄);

DOI:10.1248/cpb.38.3326

upstream raw materials:

2-formylamino-malonomonoimidic acid diamide

ethyl N-(carbamoylcyanomethyl)formamidate

formamidine hydrochloride

2-Amino-2-cyanoacetamide

Downstream raw materials:

4-amino-5-imidazolecarboxamide

4-carbamoyl-5-amino-1-<<2-(benzoyloxy)ethoxy>methyl>imidazole

2-<(4-amino-5-carbamoyl-1H-imidazol-1-yl)methoxy>ethyl benzoate

thioguanine

Refernces

• 1、 Albert. "-". . p. 500. Retrieved 1969.
• 2、 Wang, Jie,Dai, Xia-Lin,Lu, Tong-Bu,Chen, Jia-Mei. "Temozolomide-Hesperetin Drug-Drug Cocrystal with Optimized Performance in Stability, Dissolution, and Tabletability". . p. 838 - 846. Retrieved 2021.
• 3、 Wang,Stevens. "Synthetic studies of 8-carbamoylimidazo-[5,1-D]-1,2,3,5-tetrazin-4(3H)-one: A key derivative of antitumor drug temozolomide". . p. 185 - 188. Retrieved 1996.
• 4、 -. "Industrial production method of 4-amino-5-imidazolecarboxamide". Paragraph 0040; 0045-0048; 0049; 0054. . Retrieved 2020/07/15.