Sodium Carbonate → HCID 15100973, compound

HRID 1587773Notes

Reaction equation

HRID 1587773 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][C:10]([N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:14]2[N:28]=[CH:29][C:30]([C:31]#[N:32])=[C:13]12)=[O:11].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][C:10]([N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)[N:14]3[N:28]=[CH:29][C:30]([C:31]#[N:32])=[C:13]23)=[O:11])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 15100972HCID 15100972, compound

Product 1

HCID 15100973HCID 15100973, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.3 g of N-methylpiperazine, 4.4 g of 4-(chloroacetyl)-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile and 1.5 g of sodium carbonate in 75 ml of toluene was refluxed for 4 hours, then allowed to stand at room temperature overnight. The mixture was treated with 30 ml of 1N sodium hydroxide and the phases were separated. The aqueous phase was extracted twice with chloroform. The organic phases were combined, washed with water, dried, filtered and concentrated. The residue was heated to solution in 50 ml of ethyl acetate, filtered and cooled. The crystalline solid was collected, washed with ethyl acetate and hexane and dried, giving 1.8 g of the desired product, mp 178°-180° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted twice with chloroform
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. temperatureThe residue was heated to solution in 50 ml of ethyl acetate
  9. filtrationfiltered
  10. temperaturecooled
  11. customThe crystalline solid was collected
  12. washwashed with ethyl acetate and hexane
  13. customdried

Sources & evidence

ORD record
ord-f1553489a2e047d3a7bc1b378a184290
Source dataset
uspto-grants-1993_06
Patent number
US05219857

Reaction notes

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