DIFLOMOTECAN

Base Information

• Chemical Name: DIFLOMOTECAN
• CAS No.: 186668-70-2
• Molecular Formula: C21H16F2N2O4
• Molecular Weight: 398.366
• Mol file: 186668-70-2.mol

Synonyms:DIFLOMOTECAN

Chemical Property of DIFLOMOTECAN

Chemical Property:

• PSA: 81.42000
• LogP: 2.74790

Purity/Quality:

≥99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DIFLOMOTECAN

There total 17 articles about DIFLOMOTECAN 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: 48.0%

8-<(2-chloro-6,7-difluoro-3-quinolyl)methyl>-5-ethyl-1,4,5,8tetrahydro-5-hydroxyoxepino<3,4-c>pyridine-3,9-dione (209909-04-6) → 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (186668-70-2,220997-97-7)

Guidance literature:

With palladium diacetate; sodium acetate; tetra(n-tert-butyl)ammonium bromide; triphenylphosphine; In acetonitrile; for 36h; Heating;

DOI:10.1021/jm980400l

Reference yield:

→ 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (186668-70-2,220997-97-7) + 3,4-difluoroaniline (3863-11-4)

Guidance literature:

Reference yield:

1-(2-chloropyridin-4-yl)propan-1-one (87121-53-7) → 5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione (186668-70-2,220997-97-7)

Guidance literature:

Multi-step reaction with 12 steps

1: p-toluenesulfonic acid / toluene / Heating

2: acetonitrile / Heating

3: 1.) bromomesitylene, t-BuLi / 1.) THF, pentane, from -78 deg C to RT, 2 h, 2.) THF, pentane, from -78 deg C to RT, 16 h

4: NaBH₄ / methanol / 1 h

5: NaH / tetrahydrofuran / 16 h / Heating

6: aq. CF₃CO₂H / 3 h / 120 °C

7: 1.) Zn, 6N HCl / 1.) THF, reflux, 10 min, 2.) THF, reflux, 1 h

8: H₂ / 5 percent Pd/C / ethanol / 6 h / 760 Torr

9: CF₃CO₂H / 3 h / Ambient temperature

10: 49 percent / 1N HCl / 9 h / Heating

11: 33 percent / nBu₃Ph, diethyl azodicarboxylate / dimethylformamide / 3 h / 0 °C

12: 48 percent / t-Bu₄NBr, NaOAc, Ph₃P, Pd(OAc)2 / acetonitrile / 36 h / Heating

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; 2,4,6-trimethylphenyl bromide; hydrogen; tert.-butyl lithium; sodium acetate; sodium hydride; tetra(n-tert-butyl)ammonium bromide; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm980400l

upstream raw materials:

8-<(2-chloro-6,7-difluoro-3-quinolyl)methyl>-5-ethyl-1,4,5,8tetrahydro-5-hydroxyoxepino<3,4-c>pyridine-3,9-dione

1-(2-chloropyridin-4-yl)propan-1-one

4-(2-ethyl[1,3]dioxolan-2-yl)-2-methoxypyridine

2-chloro-6,7-difluoro-3-quinoline-3-carbaldehyde

Refernces

• 1、 -. "New analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them". . . Retrieved 2008/06/13.
• 2、 Lavergne, Olivier,Lesueur-Ginot, Laurence,Rodas, Francesc Pla,Kasprzyk, Philip G.,Pommier, Jacques,Demarquay, Danièle,Prévost, Grégoire,Ulibarri, Gérard,Rolland, Alain,Schiano-Liberatore, Anne-Marie,Harnett, Jeremiah,Pons, Dominique,Camara, José,Bigg, Dennis C. H.. "Homocamptothecins: Synthesis and antitumor activity of novel E-ring- modified camptothecin analogues". . p. 5410 - 5419. Retrieved 2007/10/03.