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

HRID 2306586Notes

Reaction equation

HRID 2306586 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 33 1 [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-05f41e9359894802aa0397efa2f33191
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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