1,10-Phenanthroline → HCID 18980928, compound

HRID 482600Notes

Reaction equation

HRID 482600 reaction equation
C(NC(C)C)(C)C.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([Li])CCC.[F:27][C:28]([F:52])([F:51])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([N:38]2[CH2:42][CH:41]([CH3:43])[C:40]([C:44]3[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=3)=[N:39]2)=[O:37])=[CH:31][CH:30]=1.C([O:56][CH2:57][CH3:58])(=O)C>O1CCCC1.CCCCCC>[F:52][C:28]([F:27])([F:51])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([N:38]2[CH2:42][C:41]([CH3:43])([C:57](=[O:56])[CH3:58])[C:40]([C:44]3[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=3)=[N:39]2)=[O:37])=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 13181,10-PhenanthrolineHCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 18980998HCID 18980998, compoundHCID 178418339Butyllithium

Product 1

HCID 18980928HCID 18980928, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To 14 ml (102 mmole) of diisopropyl amine and 1 mg of phenanthroline in 150 ml of tetrahydrofuran cooled to -30° C. was added 40 ml (100 mmole) of 2.5M n-butyllithium in hexane. After stirring for 5 minutes a solution of 15 g (39 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (U.S. Pat. No. 4,663,341, see experimental for compound 149) in 25 ml of tetrahydrofuran was added while maintaining the internal temperature between -30° C and -40° C. After stirring for 40 minutes the mixture was cooled to -70° C. and 20 ml of ethyl acetate was added. After stirring for 15 minutes the mixture was quenched with 20 ml of acetic acid, warmed to 0° C. and 25 ml of water was added. The organic layer was separated, concentrated in vacuo, dissolved in 200 ml of diethyl ether, washed with dilute aqueous hydrochloric acid, dilute aqueous sodium hydroxide, and brine. The mixture was dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and crystallized from diethyl ether yielding 6.5 g of the title compound containing a small amount of starting material.

Workup

  1. additionwas added
  2. temperaturewhile maintaining the internal temperature between -30° C and -40° C
  3. stirringAfter stirring for 15 minutes the mixture
  4. customwas quenched with 20 ml of acetic acid
  5. temperaturewarmed to 0° C.
  6. addition25 ml of water was added
  7. customThe organic layer was separated
  8. concentrationconcentrated in vacuo
  9. dissolutiondissolved in 200 ml of diethyl ether
  10. washwashed with dilute aqueous hydrochloric acid, dilute aqueous sodium hydroxide, and brine
  11. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customcrystallized from diethyl ether yielding 6.5 g of the title compound
  15. additioncontaining a small amount of starting material

Sources & evidence

ORD record
ord-8265e3bb39d04a299513e80952dbf15e
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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