Triethylamine hydrochloride → 6-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 1369426Notes

Reaction equation

HRID 1369426 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[F:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([NH:19][NH2:20])=O.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][C:5]2[N:4]([C:17]([C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=3[F:14])=[N:19][N:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 1362882-FluorobenzhydrazideHCID 226099503,6-Dichloro-4-(thien-2-yl)pyridazine

Product 1

HCID 226098966-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazineYield 26%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of 3,6-dichloro-4-(thien-2-yl)pyridazine from above (0.5 g, 2.1 mmol), 2-fluorobenzhydrazide (0.66 g, 4,3 mmol) and triethylamine hydrochloride (0.59 g, 4,3 mmol) in p-xylene (10 ml) was stirred and heated at reflux under nitrogen for 30 hours. Upon cooling the volatiles were removed in vacuo. The residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane to give the title compound as a yellow solid (0.19 g, 26%). MS (ES+) m/e 331 [MH]+, 333 [MH]+. This material was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 30 hours
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customThe residue was partly purified by chromatography on silica gel eluting with 50%→66%→100% ethyl acetate-hexane

Sources & evidence

ORD record
ord-ca4609a0d96f4e4fbda64e55736a09d7
Source dataset
uspto-grants-2003_06
Patent number
US06579875B1

Reaction notes

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