Sodium Carbonate → HCID 131716674, compound

HRID 893652Notes

Reaction equation

HRID 893652 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:10][C:9]([CH3:11])=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:7]2[N:19]=[CH:20][C:21]([C:22]#[N:23])=[C:6]12)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[Cl:18][C:14]1[CH:13]=[C:12]([C:8]2[N:7]3[N:19]=[CH:20][C:21]([C:22]#[N:23])=[C:6]3[N:5]([C:3](=[O:4])[CH2:2][N:39]3[CH2:38][CH2:37][N:36]([CH2:35][C:34]4[CH:42]=[CH:43][CH:44]=[C:32]([O:31][CH3:30])[CH:33]=4)[CH2:41][CH2:40]3)[CH2:10][C:9]=2[CH3:11])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 4282851-(3-methoxybenzyl)piperazineHCID 15101087HCID 15101087, compound

Product 1

HCID 131716674HCID 131716674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.7 g of 4-(chloroacetyl)-7-(3-chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile, 920 mg of sodium carbonate and 1.7 g of 3-methoxybenzyl piperazine in 100 ml of toluene was stirred for 18 hours, then treated with 25 ml of 1N sodium hydroxide and shaken. The layers were separated and the alkaline layer extracted with chloroform. This extract and the toluene layer were combined, washed with water dried, filtered and concentrated. The residual oil was triturated in ether then concentrated and dissolved with heating in 25 ml of ethanol. A 10 ml portion of 2.44 N ethanolic hydrochloric acid and an excess of ether were added and the solid was collected. This solid was crystallized from hot acetonitrile giving 1.4 g of the desired product, mp 195°-197° C.

Workup

  1. stirringshaken
  2. customThe layers were separated
  3. extractionthe alkaline layer extracted with chloroform
  4. extractionThis extract
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residual oil was triturated in ether
  10. concentrationthen concentrated
  11. dissolutiondissolved
  12. temperaturewith heating in 25 ml of ethanol
  13. additionA 10 ml portion of 2.44 N ethanolic hydrochloric acid and an excess of ether were added
  14. customthe solid was collected
  15. customThis solid was crystallized from hot acetonitrile giving 1.4 g of the desired product, mp 195°-197° C.

Sources & evidence

ORD record
ord-b84804bad864471a9dbed539cca278dc
Source dataset
uspto-grants-1992_06
Patent number
US05126340

Reaction notes

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