1-(2-fluorophenyl)-3-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea

Base Information

• Chemical Name: 1-(2-fluorophenyl)-3-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea
• CAS No.: 676128-63-5
• Molecular Formula: C₂₂H₁₇FN₄O₂
• Molecular Weight: 388.401
• UNII: 6NF9HI6D98
• DSSTox Substance ID: DTXSID101125220
• Metabolomics Workbench ID: 155335
• ChEMBL ID: CHEMBL223402
• Mol file: 676128-63-5.mol

Synonyms:1-(2-fluorophenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo(e)(1,4)diazepin-3-yl)urea;RSV 604;RSV-604;RSV604

Chemical Property of 1-(2-fluorophenyl)-3-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 388.13355396
• Heavy Atom Count: 29
• Complexity: 634

Purity/Quality:

99% ^*data from raw suppliers

RSV-604 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC(C(=O)NC3=CC=CC=C32)NC(=O)NC4=CC=CC=C4F
• Isomeric SMILES: C1=CC=C(C=C1)C2=N[C@@H](C(=O)NC3=CC=CC=C32)NC(=O)NC4=CC=CC=C4F
• Recent ClinicalTrials: Safety, Tolerability and Pharmacokinetic Study of Single and Multiple Intravenous Doses of RSV604 in Healthy Subjects.
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled study to assess the safety, tolerability, and efficacy of oral RSV604 in healthy adults experimentally infected with respiratory syncytial virus

Technology Process of 1-(2-fluorophenyl)-3-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea

There total 6 articles about 1-(2-fluorophenyl)-3-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea 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: 73.0%

1-Fluoro-2-isocyanato-benzene (16744-98-2) + (S)-3-amino-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2(3H)one (253135-95-4) → (S)-1-(2-fluorophenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)urea (676128-63-5,676128-62-4,932108-20-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jm060747l

Reference yield:

(S,S)-N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-3-phenyl-2-(3-phenylthioureido)propionamide (676127-93-8) → (S)-1-(2-fluorophenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)urea (676128-63-5,676128-62-4,932108-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 380 mg / trifluoroacetic acid / 0.67 h / 50 °C

2: 73 percent / triethylamine / tetrahydrofuran / 18 h / 20 °C

With triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jm060747l

Reference yield:

[1-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-2-phenylethyl] carbamic acid tert-butyl ester (207600-12-2) → (S)-1-(2-fluorophenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)urea (676128-63-5,676128-62-4,932108-20-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 26.1 g / hydrochloric acid / ethyl acetate / 3 h / -10 - 20 °C

2: 99 percent / CH₂Cl₂ / 18 h / 20 °C

3: 380 mg / trifluoroacetic acid / 0.67 h / 50 °C

4: 73 percent / triethylamine / tetrahydrofuran / 18 h / 20 °C

With hydrogenchloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm060747l

upstream raw materials:

1-Fluoro-2-isocyanato-benzene

(S)-3-amino-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2(3H)one

(S,S)-N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-3-phenyl-2-(3-phenylthioureido)propionamide

[1-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-2-phenylethyl] carbamic acid tert-butyl ester

Downstream raw materials:

(S)-{3-[3-(2-fluorophenyl)ureido]-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl}acetic acid methyl ester

(S)-{3-[3-(2-fluorophenyl)ureido]-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl}acetic acid

(S)-1-(2-fluoro-phenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-urea besylate monohydrate

(S)-1-(2-fluoro-phenyl)-3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-urea besylate