Water → HCID 131716677, compound

HRID 893656Notes

Reaction equation

HRID 893656 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].[F:24][C:25]1[CH:37]=[CH:36][CH:35]=[CH:34][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.O>O1CCCC1>[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:31]3[CH2:30][CH2:29][N:28]([CH2:27][C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[F:24])[CH2:33][CH2:32]3)[CH2:10][C:9]=2[CH3:11])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7961681-[(2-Fluorophenyl)methyl]piperazineHCID 15101087HCID 15101087, compound

Product 1

HCID 131716677HCID 131716677, compoundYield 112.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.8 g of 4-(chloroacetyl)-7-(3-chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile, 3 g of 2-fluorobenzylpiperazine and 3.4 g of triethylamine in 200 ml of tetrahydrofuran was stirred under reflux for 18 hours, then cooled and treated with 750 ml of water. The resulting oil was extracted into dichloromethane, dried filtered and concentrated to a red-orange viscous oil. This oil was dissolved in 50 ml of acetonitrile and an excess of ether and 18 ml of 3.74N ethanolic hydrochloric acid added. After standing overnight the solid was collected, washed with ethanol and ether, dried and recrystallized from ethanol, giving 4.5 g of the desired product, mp 192°-194° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperaturecooled
  3. extractionThe resulting oil was extracted into dichloromethane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to a red-orange viscous oil
  7. dissolutionThis oil was dissolved in 50 ml of acetonitrile
  8. additionan excess of ether and 18 ml of 3.74N ethanolic hydrochloric acid added
  9. customthe solid was collected
  10. washwashed with ethanol and ether
  11. customdried
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dea97649b49748938ffb0edf4b39676e
Source dataset
uspto-grants-1992_06
Patent number
US05126340

Reaction notes

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