Hydrochloric Acid → 3-[2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine

HRID 476905Notes

Reaction equation

HRID 476905 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][C:27]([F:30])=[CH:26][C:25]=2[F:31])[CH2:20][CH2:19]1.Cl.[OH-].[Na+]>C(O)C.C(N(CC)CC)C.CCOCC>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[N:21]1[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][S:1][C:2]2[N:6]3[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([F:13])([F:14])[F:12])[C:5]3=[N:4][N:3]=2)[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 141267481-(2-Chloroethyl)-4-(2,4-difluorophenyl)piperazineHCID 178506204HCID 178506204, compound

Product 1

HCID 141267513-[2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridineYield 58.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 13 g of 3-mercapto-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine, prepared in Example 18, and 15.5 g of 1-chloro-2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethane as the base, freed from its hydrochloride, prepared in Example 7, by the addition of sodium hydroxide and extraction with ether, in 75 ml of ethanol containing 10 ml of triethylamine is heated under reflux for 6 hours. The reaction mixture is then concentrated in vacuo and the residue is taken up with methylene chloride, which is washed carefully with water, dried and then evaporated. The residue crystallizes when taken up in a mixture of ethyl ether and isopropyl ether. The crystals obtained are filtered off, washed with isopropyl ether and then dried to give 15.5 g of 3-[2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethylmercapto]-8-trifluoromethyl-1,2,4-triazolo(4,3-a)pyridine in the form of crystals melting at 119°-120° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. washis washed carefully with water
  5. customdried
  6. customevaporated
  7. customThe residue crystallizes when
  8. additiontaken up in a mixture of ethyl ether and isopropyl ether
  9. customThe crystals obtained
  10. filtrationare filtered off
  11. washwashed with isopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-9e9907dd858840ec8bb7795577e22c73
Source dataset
uspto-grants-1989_12
Patent number
US04886805

Reaction notes

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