Olprinone

Base Information

• Chemical Name: Olprinone
• CAS No.: 106730-54-5
• Molecular Formula: C14H10N4
• Molecular Weight: 250.25
• Hs Code.: 29183000
• UNII: 4Y8BMI9YGC
• DSSTox Substance ID: DTXSID1048461
• Nikkaji Number: J395.965A
• Wikipedia: Olprinone
• Wikidata: Q7088538
• NCI Thesaurus Code: C90918
• Pharos Ligand ID: XB1JDTBU2ZZF
• Metabolomics Workbench ID: 155639
• ChEMBL ID: CHEMBL1474900
• Mol file: 106730-54-5.mol

Synonyms:1,2-dihydro-6-methyl-2-oxo-5-(imidazo(1,2-a)pyridin-6-yl)-3-pyridinecarbonitrile;E 1020;E-1020;loprinone hydrochloride;olprinone

Chemical Property of Olprinone

Chemical Property:

• Melting Point: >300oC
• Refractive Index: 1.702
• PKA: 6.59±0.10(Predicted)
• PSA: 73.95000
• Density: 1.346 g/cm³
• LogP: 1.86968
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 250.08546096
• Heavy Atom Count: 19
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

Olprinone 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,C
• Hazard Codes: T,N,C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C(=O)N1)C#N)C2=CN3C=CN=C3C=C2
• Recent NIPH Clinical Trials: A safety study of perioperative olprinone administration for liver resection

Technology Process of Olprinone

There total 12 articles about Olprinone 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: 87.9%

4-dimethylamino-3-(6-imidazo<1,2-a>pyridinyl)-3-buten-2-one (106730-70-5) + cyanoacetic acid amide (107-91-5) → olprinone (106730-54-5)

Guidance literature:

With sodium methylate; In ethanol; for 1h; Time; Reflux;

Reference yield: 71.7%

(imidazo[1,2-a]pyridin-6-yl)boronic acid (913835-63-9) + 5-bromo-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (84725-13-3) → olprinone (106730-54-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In toluene; at 90 - 100 ℃; for 24h; Temperature; Solvent; Inert atmosphere;

Reference yield:

6-bromoimidazo[1,2-a]pyridine (6188-23-4) → olprinone (106730-54-5)

Guidance literature:

Multi-step reaction with 4 steps

2: 70.5 percent / ozone, conc. HCl / H₂O; methanol / -5 - 0 °C

3: 74.5 percent / dimethylformamide / 1 h / 80 °C

4: 50.9 percent / NaOCH₃ / dimethylformamide / 12 h / 80 - 90 °C

With hydrogenchloride; sodium methylate; ozone; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.1556

upstream raw materials:

4-dimethylamino-3-(6-imidazo<1,2-a>pyridinyl)-3-buten-2-one

cyanoacetic acid amide

5-bromo-2-pyridylamine

methyl 6-aminonicotinoate

Downstream raw materials:

2-benzyloxy-5-imidazo<1,2-a>pyridin-6-yl-6-methyl-3-pyridinecarbonitrile

1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridine carbonitrile hydrochloride

2-benzyloxy-5-(2,3-dihydro-2-oxoimidazo<1,2-a>pyridin-6-yl)-6-methyl-3-pyridinecarbonitrile hydrobromide

2-{6'-Benzyloxy-5'-cyano-2'-methyl-6-[(E)-toluene-4-sulfonylimino]-6H-[3,3']bipyridinyl-1-yl}-acetamide

Refernces

• 1、 -. "Preparation method of olprinone and 9-azaindole-5-boric acid". . . Retrieved 2017/07/15.
• 2、 -. "3-cyano-5-(6-imidazo[1,2-a]pyridyl)pyridin-2-ols useful as cardiotonics". . . Retrieved 2008/06/13.