1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione

Base Information

• Chemical Name: 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione
• CAS No.: 477933-12-3
• Molecular Formula: C13H12FNO3
• Molecular Weight: 249.23800
• DSSTox Substance ID: DTXSID90468094
• Wikidata: Q82295194
• Mol file: 477933-12-3.mol

Synonyms:477933-12-3;1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione;1-(2-Cyclopropylethyl)-6-fluorobenzo[d][1,3]oxazine-2,4-dione;1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;1-(2-CYCLOPROPYLETHYL)-6-FLUORO-3,1-BENZOXAZINE-2,4-DIONE;SCHEMBL3924246;DTXSID90468094;AKOS015902274;AG-F-62565;FT-0665411;C15840;A898256;2H-3,1-Benzoxazine-2,4(1H)-dione, 1-(2-cyclopropylethyl)-6-fluoro-

Chemical Property of 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione

Chemical Property:

• Melting Point: 73-75°C
• PSA: 52.21000
• LogP: 1.89390
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 249.08012141
• Heavy Atom Count: 18
• Complexity: 369

Purity/Quality:

99%min ^*data from raw suppliers

1-(2-Cyclopropylethyl)-6-fluorobenzo[d][1,3]oxazine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CCN2C3=C(C=C(C=C3)F)C(=O)OC2=O
• Uses: Intermediate in the synthesis of HCV polymerase inhibitors.

Technology Process of 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione

There total 3 articles about 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 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: 84.0%

5-fluoroisatoic anhydride (321-69-7) + 1-cyclopropylethanol (2566-44-1) → 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (477933-12-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; Product distribution / selectivity;

Reference yield:

2-amino-5-fluorobenzoic acid (446-08-2) → 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (477933-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / tetrahydrofuran; toluene

2: 51 percent / Ph₃P; diethyl azodicarboxylate / CHCl₃

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; chloroform; toluene; 2: Mitsunobu reaction;

DOI:10.1021/jm050855s

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + C12H14FNO2 (477932-69-7) → 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (477933-12-3)

Guidance literature:

With potassium carbonate; In ethyl acetate;

DOI:10.1016/j.bmcl.2009.04.119

upstream raw materials:

5-fluoroisatoic anhydride

1-cyclopropylethanol

2-amino-5-fluorobenzoic acid

bis(trichloromethyl) carbonate

Downstream raw materials:

ethyl 1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate

Refernces

• 1、 Hendricks, Robert T.,Fell, Jay B.,Blake, James F.,Fischer, John P.,Robinson, John E.,Spencer, Stacey R.,Stengel, Peter J.,Bernacki, April L.,Leveque, Vincent J.P.,Pogam, Sophie Le,Rajyaguru, Sonal,Najera, Isabel,Josey, John A.,Harris, Jason R.,Swallow, Steven. "Non-nucleoside inhibitors of HCV NS5B polymerase. Part 1: Synthetic and computational exploration of the binding modes of benzothiadiazine and 1,4-benzothiazine HCV NS5b polymerase inhibitors". scheme or table. p. 3637 - 3641. Retrieved 2010/04/05.