Fadrozole

Base Information

• Chemical Name: Fadrozole
• CAS No.: 102676-47-1
• Molecular Formula: C₁₄H₁₃N₃
• Molecular Weight: 223.277
• Hs Code.: 2933990090
• European Community (EC) Number: 862-508-6
• UNII: H3988M64PU
• DSSTox Substance ID: DTXSID5034141
• Nikkaji Number: J366.696D
• Wikipedia: Fadrozole
• Wikidata: Q5429279
• NCI Thesaurus Code: C79911
• Pharos Ligand ID: MSK42XHU1T6H
• ChEMBL ID: CHEMBL9298
• Mol file: 102676-47-1.mol

Synonyms:CGS 020286A;CGS 16949A;CGS-020286A;CGS-16949A;CGS020286A;CGS16949A;FAD 286;FAD-286;FAD286;Fadrozole;Fadrozole Hydrochloride;Fadrozole Monohydrochloride;Hydrochloride, Fadrozole;Monohydrochloride, Fadrozole

Chemical Property of Fadrozole

Chemical Property:

• Vapor Pressure: 1.95E-09mmHg at 25°C
• Melting Point: 0°C
• Boiling Point: 0°C
• PKA: 7.16±0.40(Predicted)
• Flash Point: 245.1°C
• PSA: 41.61000
• Density: 1.2g/cm³
• LogP: 2.68048
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 223.110947427
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

98%min ^*data from raw suppliers

Fadrozole ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N2C=NC=C2C1)C3=CC=C(C=C3)C#N
• Recent EU Clinical Trials: DP13 – A Phase II Study in Patients with Primary Aldosteronism to Evaluate the Efficacy, Safety and Tolerability of the Aldosterone Synthase Inhibitor, DP13, over an 8-week Treatment Period
• Uses: Antineoplastic

Technology Process of Fadrozole

There total 11 articles about Fadrozole 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: 85.0%

5-(4-carbamylphenyl)-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine (102676-43-7) → fadrozole (102676-47-1,102676-86-8,102676-87-9,131833-76-6)

Guidance literature:

With trichlorophosphate; In chloroform; for 15h; Heating;

DOI:10.1021/jm00106a038

Reference yield:

ethyl 4-(2-pyridinyl)benzoate (4385-61-9) → fadrozole (102676-47-1,102676-86-8,102676-87-9,131833-76-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 40percent peracetic acid / 3 h / 90 °C

2: 1.) dimethyl sulfate / 1.) toluene, 90 deg C, 3 h, 2.) water, 0 deg C, 24 h

3: 65 percent / H₂, conc. HCl / 10percent Pd/C / methanol / 760 Torr

4: 83 percent / 15 h / 90 °C

5: 73 percent / POCl₃ / toluene / 15 h / 90 °C

6: 85 percent / H₂, conc. HCl / 10percent Pd/C / ethanol / 4 h / 60 °C / 2068.6 Torr

7: 95 percent / 1 N NaOH / ethanol / 3 h / Heating

8: SOCl₂ / 0.5 h / Heating

9: NH₃ (gas) / CH₂Cl₂ / 15 h

10: 85 percent / POCl₃ / CHCl₃ / 15 h / Heating

With hydrogenchloride; peracetic acid; sodium hydroxide; thionyl chloride; ammonia; hydrogen; dimethyl sulfate; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jm00106a038

Reference yield:

2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide (102676-38-0) → fadrozole (102676-47-1,102676-86-8,102676-87-9,131833-76-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) dimethyl sulfate / 1.) toluene, 90 deg C, 3 h, 2.) water, 0 deg C, 24 h

2: 65 percent / H₂, conc. HCl / 10percent Pd/C / methanol / 760 Torr

3: 83 percent / 15 h / 90 °C

4: 73 percent / POCl₃ / toluene / 15 h / 90 °C

5: 85 percent / H₂, conc. HCl / 10percent Pd/C / ethanol / 4 h / 60 °C / 2068.6 Torr

6: 95 percent / 1 N NaOH / ethanol / 3 h / Heating

7: SOCl₂ / 0.5 h / Heating

8: NH₃ (gas) / CH₂Cl₂ / 15 h

9: 85 percent / POCl₃ / CHCl₃ / 15 h / Heating

With hydrogenchloride; sodium hydroxide; thionyl chloride; ammonia; hydrogen; dimethyl sulfate; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jm00106a038

upstream raw materials:

5-(4-carbamylphenyl)-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine

5-(3-chloropropyl)-1-<(4-cyanophenyl)methyl>-1H-imidazole

ethyl 4-(2-pyridinyl)benzoate

2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide

Refernces