Triethylamine hydrochloride → HCID 11066622, compound

HRID 2306578Notes

Reaction equation

HRID 2306578 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH:8]1[CH2:11][CH2:10][CH2:9]1.[F:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([NH:18][NH2:19])=O.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([CH:8]2[CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]2[N:4]([C:16]([C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=3[F:13])=[N:18][N:19]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 1362882-FluorobenzhydrazideHCID 219732193,6-Dichloro-4-cyclobutylpyridazine

Product 1

HCID 11066622HCID 11066622, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of 3,6-dichloro-4-cyclobutylpyridazine from above (3.0 g, 14.7 mmol), 2-fluorobenzhydrazide (3.0 g, 19.5 mmol) and triethylamine hydrochloride (3.0 g, 21.8 mmol) in p-xylene (50 ml) was stirred and heated at reflux under a stream of nitrogen for 20 hours. Upon cooling the volatiles were removed in vacuo. The residue was partitioned between dichloromethane and water. The aqueous was basified by the addition of solid potassium carbonate. Some dark insoluble material was removed by filtration at this stage. The aqueous was further extracted with dichloromethane (×2). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel eluting with 20%→30% ethyl acetate/dichloromethane to give the title compound (2.2 g, 49%) as a light-brown solid. Data for the title compound: 1H NMR (250 MHz, CDCl3) δ 1.85-2.08 (1H, m), 2.08-2.30 (3H, m), 2.38-2.64 (2H, m), 3.62-3.84 (1H, m), 7.19-7.46 (2H, m), 7.46-7.67 (1H, m), 7.80-7.96 (1H, m), 7.99 (1H, s), MS (ES+) m/e 303 [MH]+, 305 [MH]+.

Workup

  1. temperatureheated
  2. temperatureat reflux under a stream of nitrogen for 20 hours
  3. temperatureUpon cooling the volatiles
  4. customwere removed in vacuo
  5. customThe residue was partitioned between dichloromethane and water
  6. additionThe aqueous was basified by the addition of solid potassium carbonate
  7. customSome dark insoluble material was removed by filtration at this stage
  8. extractionThe aqueous was further extracted with dichloromethane (×2)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by chromatography on silica gel eluting with 20%→30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-365959f10db3430da64dee528f515630
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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