Sodium Carbonate → HCID 15712539, compound

HRID 1088691Notes

Reaction equation

HRID 1088691 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[N:20]2[CH:34]=[N:35][C:36]([C:37]#[N:38])=[C:19]12)=[O:17].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[C:2]1([CH2:1][N:8]2[CH2:13][CH2:12][N:11]([CH2:15][C:16]([N:18]3[CH2:23][CH:22]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=4)[N:20]4[CH:34]=[N:35][C:36]([C:37]#[N:38])=[C:19]34)=[O:17])[CH2:10][CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 66225Magnesium orthosilicateHCID 759941-BenzylpiperazineHCID 15712537HCID 15712537, compound

Product 1

HCID 15712539HCID 15712539, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A stirred mixture of 1.6 g of 1-benzylpiperazine, 2.9 g of 1-(chloroacetyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile and 1.1 g of sodium carbonate in 55 ml of toluene was heated at reflux for 18 hours. The reaction mixture was cooled, then shaken with 20 ml of 1N sodium hydroxide. The layers were separated and the aqueous phase was extracted once with chloroform. The toluene phase above, and the chloroform extract were combined and washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a viscous oil. The oil was dissolved in 50 ml of chloroform and passed through hydrous magnesium silicate. The chloroform filtrate was concentrated to an oil. The oil was heated to solution in 25 ml of ethyl acetate and filtered. Then 25 ml of n-hexane was added to the filtrate to crystallize the product. The crystals were collected by filtration, pressed to remove solvent, washed with hexane and dried to give 3.4 g of the product of the example as cream colored crystals, mp 167°-169° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted once with chloroform
  6. extractionThe toluene phase above, and the chloroform extract
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto obtain a viscous oil
  12. concentrationThe chloroform filtrate was concentrated to an oil
  13. temperatureThe oil was heated to solution in 25 ml of ethyl acetate
  14. filtrationfiltered
  15. additionThen 25 ml of n-hexane was added to the filtrate
  16. customto crystallize the product
  17. filtrationThe crystals were collected by filtration
  18. customto remove solvent
  19. washwashed with hexane
  20. customdried

Sources & evidence

ORD record
ord-e008f23ec1fd447d853b5876cee19ef1
Source dataset
uspto-grants-1990_10
Patent number
US04963552

Reaction notes

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