Triethylamine hydrochloride → HCID 22609916, compound

HRID 1369423Notes

Reaction equation

HRID 1369423 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1([CH3:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[F:16][C:17]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=1[C:19]([NH:21][NH2:22])=O.Cl.C(N(CC)CC)C>CC1C=CC(C)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2([CH3:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]2[N:4]([C:19]([C:18]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:17]=3[F:16])=[N:21][N:22]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 27369222,4-Difluorobenzoic acid hydrazideHCID 22609937HCID 22609937, compound

Product 1

HCID 22609916HCID 22609916, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of 3,6-dichloro-4-(1-methylcyclohexyl)pyridazine (1.29 g, 5.27 mmol), 2,4-difluorobenzoic hydrazide (1.72 g, 10 mmol) and triethylamine hydrochloride (1.09 g, 7.9 mmol) in p-xylene (5 ml) was stirred and heated at reflux for 24 hours. Upon cooling, the volatiles were removed in vacuo and the residue was partitioned between dichloromethane (100 ml) and water (100 ml) and NaHCO3 (100 ml). Undissolved solid was removed by filtration. The layers were separated and the aqueous was further extracted with dichloromethane (2×100 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with 0%→25% ethyl acetate in dichloromethane to give the required product (0.74 g): 1H NMR (250 MHz, CDCl3) δ1.34-1.74 (6H, m), 1.50 (3H, s), 1.90-2.15 (4H, m), 7.01-7.14 (2H, m), 7.87-7.98 (1H, m), 8.18 (1H, s); MS (ES+) m/e 365 [MH]+, 363 [MH]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperatureUpon cooling
  4. customthe volatiles were removed in vacuo
  5. customthe residue was partitioned between dichloromethane (100 ml) and water (100 ml) and NaHCO3 (100 ml)
  6. customwas removed by filtration
  7. customThe layers were separated
  8. extractionthe aqueous was further extracted with dichloromethane (2×100 ml)
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by chromatography on silica eluting with 0%→25% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-23d850436baf44e8848985867fb109b9
Source dataset
uspto-grants-2003_06
Patent number
US06579875B1

Reaction notes

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