Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate
• CAS No.: 103772-13-0
• Molecular Formula: C15H13 F3 N2 O3
• Molecular Weight: 326.275
• DSSTox Substance ID: DTXSID00556315
• Wikidata: Q82437829
• Mol file: 103772-13-0.mol

Synonyms:103772-13-0;1-Cyclopropyl-5-Amido-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3- Quinolinecarboxylic acid ethyl ester;ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate;1-Cyclopropyl-5-amido-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester;BOFBKJLYZUFZMV-UHFFFAOYSA-N;SCHEMBL1344898;DTXSID00556315;AKOS015963335;Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate;ethyl 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate;ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate;Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property of Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate

Chemical Property:

• PSA: 74.32000
• LogP: 3.09380
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 326.08782677
• Heavy Atom Count: 23
• Complexity: 552

Purity/Quality:

98.5% ^*data from raw suppliers

1-CYCLOPROPYL-5-AMIDO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=C(C(=C(C(=C2C1=O)N)F)F)F)C3CC3

Technology Process of Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate

There total 15 articles about Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate 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: 100.0%

ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate (103772-12-9) → ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (103772-13-0)

Guidance literature:

With hydrogen; RaNi; In tetrahydrofuran; ethanol; for 12h; under 1034.3 Torr;

DOI:10.1021/jm00107a039

Reference yield: 89.0%

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate (110872-04-3) → ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (103772-13-0)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In acetic acid; at 50 ℃; for 2h; under 760.051 Torr;

Reference yield:

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3) → ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (103772-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / triethylamine / toluene / 1 h / Heating

2: 80 percent / H₂ / 5percent Pd/C / acetic acid; ethanol / Ambient temperature

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; acetic acid; toluene;

DOI:10.1021/jm00168a018

upstream raw materials:

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate

ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate

2,3,4,5-tetrafluorobenzoic acid

2,3,4,5-tetrafluoro-6-nitrobenzoic acid

Downstream raw materials:

5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

sparfloxacin

5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Refernces

• 1、 Cociorva, Oana M.,Li, Bei,Nomanbhoy, Tyzoon,Li, Qiang,Nakamura, Ayako,Nakamura, Kai,Nomura, Masahiro,Okada, Kyoko,Seto, Shigeki,Yumoto, Kazuhiro,Liyanage, Marek,Zhang, Melissa C.,Aban, Arwin,Leen, Brandon,Szardenings, Anna Katrin,Rosenblum, Jonathan S.,Kozarich, John W.,Kohno, Yasushi,Shreder, Kevin R.. "Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β". scheme or table. p. 5948 - 5951. Retrieved 2011/10/18.
• 2、 -. "Process for preparing a quinolone-carboxylic acid". . . Retrieved 2008/06/13.