Triethylamine → 3-[2-(4-(3-Trifluoromethylphenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine maleate

HRID 476904Notes

Reaction equation

HRID 476904 reaction equation
[SH:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:5]2=[N:4][N:3]=1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45]>C(O)C.CC(C)=O>[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45].[F:33][C:30]([F:31])([F:32])[C:26]1[CH:25]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][S:1][C:2]3[N:6]4[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:13])([F:14])[F:12])[C:5]4=[N:4][N:3]=3)[CH2:23][CH2:22]2)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 444266Maleic AcidHCID 112548451-(2-Chloroethyl)-4-[3-(trifluoromethyl)phenyl]piperazineHCID 178506204HCID 178506204, compound

Product 1

HCID 867435673-[2-(4-(3-Trifluoromethylphenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine maleateYield 44.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 702EthanolSolvent

Procedure

A solution of 11 g of 3-mercapto-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine, prepared in Example 18, and 15 g of 1-chloro-2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethane in 75 ml of ethanol containing 8 ml of triethylamine is heated under reflux for 6 hours. The reaction mixture is then concentrated in vacuo, water and ice are added and the extraction is carried out with ether. The organic phase is washed with water, with a dilute solution of sodium hydroxide and then again with water. The ether phase is dried and then concentrated and the residue obtained (21.5 g) is dissolved in acetone. A solution of 5.1 g of maleic acid in acetone is added to this acetone solution. The crystals which then form are filtered off, washed with acetone and ether and dried to give 11.5 g of 3-[2-(4-(3-trifluoromethylphenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine maleate in the form of crystals melting at 144°-5° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture is then concentrated in vacuo, water and ice
  4. additionare added
  5. extractionthe extraction
  6. washThe organic phase is washed with water, with a dilute solution of sodium hydroxide
  7. dry with materialThe ether phase is dried
  8. concentrationconcentrated
  9. customthe residue obtained (21.5 g)
  10. customThe crystals which then form
  11. filtrationare filtered off
  12. washwashed with acetone and ether
  13. customdried

Sources & evidence

ORD record
ord-344183d781374115b6f8a413dc83e1c4
Source dataset
uspto-grants-1989_12
Patent number
US04886805

Reaction notes

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