Hydrochloric Acid → HCID 15101055, compound

HRID 1587788Notes

Reaction equation

HRID 1587788 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][C:9]([CH2:11][CH3:12])=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:7]2[N:23]=[CH:24][C:25]([C:26]#[N:27])=[C:6]12)=[O:4].[CH2:28]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].Cl>C1(C)C=CC=CC=1.CCOCC>[CH2:11]([C:9]1[CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:38]2[CH2:39][CH2:40][N:35]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:36][CH2:37]2)[C:6]2[N:7]([N:23]=[CH:24][C:25]=2[C:26]#[N:27])[C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=1)[CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 759941-BenzylpiperazineHCID 19756204HCID 19756204, compound

Product 1

HCID 15101055HCID 15101055, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.3 g of 4-(chloroacetyl)4,5-dihydro-6-ethyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 1.6 ml of 1-benzylpiperazine and 1 g. of sodium carbonate in 110 ml of toluene was stirred and refluxed for 18 hours. The mixture was treated with 10 ml of 5N sodium hydroxide and the organic phase was separated, dried over sodium sulfate and evaporated to give a dark oil. This was dissolved in ether and combined with ethanolic hydrogen chloride to give a white solid and this solid was recrystallized from acetonitrile to give 3.4 g of the title compound, m.p. 184°-186° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto give a dark oil
  6. customto give a white solid
  7. customthis solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-46b66b25bd5d4278a240b8a6fa25f1d6
Source dataset
uspto-grants-1993_06
Patent number
US05219857

Reaction notes

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