Triethylamine → HCID 21187546, compound

HRID 1383819Notes

Reaction equation

HRID 1383819 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[C:15]([NH:23][NH2:24])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]2[N:4]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:23][N:24]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 6401291HCID 6401291, compound

Product 1

HCID 21187546HCID 21187546, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture of 3,6-dichloro-4-(piperidin-1-yl)pyridazine (0.55 g, 2.4 mmol), benzoyl hydrazine (370 mg, 2.7 mmol), triethylamine (375 ml, 2.7 mmol) and p-toluenesulphonic acid monohydrate (510 mg, 2.7 mmol) in xylene (mixture of isomers, 10 ml) was stirred and heated at reflux under nitrogen for 24 hours. Upon cooling the xylene was removed in vacuo and the residue was partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane (×3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 30% ethyl acetate/dichloromethane to afford the undesired regioisomer (less polar) (177 mg, 23%) and the title compound (383 mg, 50%) (more polar). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ 1.62-1.86 (6H, m), 3.09-3.13 (4H, m), 7.42 (1H, s), 7.50-7.60 (3H, m), 8.40-8.44 (2H, m).

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 24 hours
  3. customwas removed in vacuo
  4. customthe residue was partitioned between dichloromethane and water
  5. extractionThe aqueous was further extracted with dichloromethane (×3)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with 30% ethyl acetate/dichloromethane
  11. customto afford the undesired regioisomer (less polar) (177 mg, 23%)

Sources & evidence

ORD record
ord-22efd50c645d4ef0b59106f1ba1be76e
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

Loading…