Triethylamine → HCID 15035140, compound

HRID 1656423Notes

Reaction equation

HRID 1656423 reaction equation
C([N:3]([CH2:6]C)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13](C(O)=O)=[C:12]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[F:45][C:46]1[CH:52]=[CH:51][CH:50]=[C:49]([F:53])[C:47]=1[NH2:48]>O.O1CCOCC1>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH:3][C:6]([NH:48][C:47]1[C:46]([F:45])=[CH:52][CH:51]=[CH:50][C:49]=1[F:53])=[O:35])=[C:12]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 796472,6-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 103791113-Quinolinecarboxylic acid, 6-chloro-4-phenyl-

Product 1

HCID 15035140HCID 15035140, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (0.34 ml) was added to a mixture of 6-chloro-4-phenyl-3-quinolinecarboxylic acid (566 mg), diphenylphosphoryl azide (660 ml) and dioxane (10 ml). The mixture was stirred for 15 mins. at room temperature and then for 20 mins. under reflux. After cooling, 2,6-difluoroaniline (310 mg) was added to the mixture. It was stirred for 15 mins. at room temperature and then for 30 mins. under reflux. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate and water, successively. After being dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized to give 6-chloro-3-[3-(2,6-difluorophenyl)ureido]-4-phenylquinoline as colorless needles. Yield 562 mg (68.7%). m.p. 228°-229° C.

Workup

  1. waitat room temperature and then for 20 mins
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. stirringIt was stirred for 15 mins
  5. waitat room temperature and then for 30 mins
  6. temperatureunder reflux
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate and water
  9. dry with materialAfter being dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue was recrystallized

Sources & evidence

ORD record
ord-8f0565235c4d41cdbc4ad7a15ab7b7f0
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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