Firategrast

Base Information

• Chemical Name: Firategrast
• CAS No.: 402567-16-2
• Molecular Formula: C27H27F2NO6
• Molecular Weight: 499.5
• UNII: OJY3SK9H5F
• DSSTox Substance ID: DTXSID00433031
• NCI Thesaurus Code: C76692
• Metabolomics Workbench ID: 153668
• ChEMBL ID: CHEMBL2104967
• Mol file: 402567-16-2.mol

Synonyms:(1,1'-biphenyl)-4-propanoic acid, .alpha.-((2,6-difluorobenzoyl)amino)-4'(ethoxymethyl)-2',6'-dimethoxy-,(.alpha.S)-;(2S)-2-((2,6- difluorobenzoyl)amino)-3-(4'-(ethoxymethyl)-2',6'-dimethoxybiphenyl-4- yl)propanoic acid;Firategrast;SB-683699;SB683699

Chemical Property of Firategrast

Chemical Property:

• Melting Point: 154-155℃ (ethanol water )
• Boiling Point: 594.4±50.0 °C(Predicted)
• PKA: 3.51±0.10(Predicted)
• PSA: 97.58000
• Density: 1.261±0.06 g/cm3(Predicted)
• LogP: 5.18600
• Solubility.: ≥50 mg/mL in DMSO; insoluble in H2O; ≥90.8 mg/mL in EtOH with gentle warming
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 499.18064391
• Heavy Atom Count: 36
• Complexity: 680

Purity/Quality:

98% min ^*data from raw suppliers

Firategrast(SB-683699) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOCC1=CC(=C(C(=C1)OC)C2=CC=C(C=C2)CC(C(=O)O)NC(=O)C3=C(C=CC=C3F)F)OC
• Isomeric SMILES: CCOCC1=CC(=C(C(=C1)OC)C2=CC=C(C=C2)C[C@@H](C(=O)O)NC(=O)C3=C(C=CC=C3F)F)OC
• Recent ClinicalTrials: Study Of White Blood Cells In The Cerebrospinal Fluid And Blood Of Patients With Relapsing Forms Of Multiple Sclerosis
• Recent EU Clinical Trials: An open-label study of leukocyte counts in the cerebrospinal fluid and blood of subjects with relapsing forms of multiple sclerosis following treatment with firategrast
• Uses: Treatment of multiple sclerosis and inflammatory bowel disease.

Technology Process of Firategrast

There total 4 articles about Firategrast 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: 71.0%

ethyl (2S)-2-{[(2,6-difluorophenyl)carbonyl]amino}-3-[4'-[(ethyloxy)methyl]-2',6'-bis(methyloxy)-4-biphenylyl]propanoate → firategrast (402567-16-2)

Guidance literature:

ethyl (2S)-2-{[(2,6-difluorophenyl)carbonyl]amino}-3-[4'-[(ethyloxy)methyl]-2',6'-bis(methyloxy)-4-biphenylyl]propanoate; With potassium hydroxide; In tetrahydrofuran; water; at 7 - 13 ℃; Industry scale;

With citric acid; In tetrahydrofuran; water; toluene; at 47 - 53 ℃; Industry scale;

Reference yield:

(S)-ethyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride (232276-00-5) → firategrast (402567-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / water; Me-THF / 0.5 h / 7 - 28 °C / Industry scale

2.1: diisopropylamine / / water; Me-THF / 3 h / 72 - 78 °C / Inert atmosphere; Industry scale

3.1: potassium hydroxide / water; tetrahydrofuran / 7 - 13 °C / Industry scale

3.2: 47 - 53 °C / Industry scale

With potassium carbonate; diisopropylamine; potassium hydroxide; In tetrahydrofuran; Me-THF; water; 2.1: Suzuki Coupling;

Reference yield:

2,6-difluorobenzoylchloride (18063-02-0) → firategrast (402567-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / water; Me-THF / 0.5 h / 7 - 28 °C / Industry scale

2.1: diisopropylamine / / water; Me-THF / 3 h / 72 - 78 °C / Inert atmosphere; Industry scale

3.1: potassium hydroxide / water; tetrahydrofuran / 7 - 13 °C / Industry scale

3.2: 47 - 53 °C / Industry scale

With potassium carbonate; diisopropylamine; potassium hydroxide; In tetrahydrofuran; Me-THF; water; 2.1: Suzuki Coupling;

upstream raw materials:

2,6-difluorobenzoylchloride

(S)-ethyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride