Pyridazine → HCID 59367705, compound

HRID 1253597Notes

Reaction equation

HRID 1253597 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[N:13]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>ClCCl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH:27]3[CH:26]=[CH:25][N:24]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:23]=[CH:28]3)=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[N:13]=1

Participants

5

Reactant 3

HCID 9259Pyridazine2×HCID 10928Ethyl chloroformate2×HCID 137233Imidazo(1,2-b)pyridazine, 6-chloro-2-phenyl-

Product 1

HCID 59367705HCID 59367705, compoundYield 260.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

26.2 ml (30.3 mmol) of ethyl chloroformate are added, dropwise in 30 minutes, to a solution of 25.2 g (109 mmol) of 6-chloro-2-phenylimidazo[1,2-b]pyridazine and 39.8 ml (548 mmol) of pyridazine in 550 ml of dichloromethane at 8° C. The medium is stirred at 10° C. for a further hour and then left to stir for an additional hour. The medium is cooled to 8° C. and 14.9 ml (273 mmol) of pyridazine and 13.1 ml (137 mmol) of ethyl chloroformate are then added in fifteen minutes. The reaction is allowed to return to ambient temperature with stirring for a further hour. The solvent is evaporated off under reduced pressure and the residue is taken up with 1 l of ethyl acetate. The organic phase is washed with a saturated solution of sodium hydrogen carbonate and then with water. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The product is chromatographed on a neutral alumina column, elution being carried out with a mixture of chloroform and cyclohexane (6/4), to give 35 g of an orangey solid, which is crystallized from 250 ml of diethyl ether, to give 30.1 g of a beige solid.

Workup

  1. waitleft
  2. stirringto stir for an additional hour
  3. temperatureThe medium is cooled to 8° C.
  4. customto return to ambient temperature
  5. stirringwith stirring for a further hour
  6. customThe solvent is evaporated off under reduced pressure
  7. washThe organic phase is washed with a saturated solution of sodium hydrogen carbonate
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. customthe solvent is evaporated off under reduced pressure
  10. customThe product is chromatographed on a neutral alumina column, elution
  11. additionbeing carried out with a mixture of chloroform and cyclohexane (6/4)
  12. customto give 35 g of an orangey solid, which
  13. customis crystallized from 250 ml of diethyl ether

Sources & evidence

ORD record
ord-fd5ae66a87634f89a505dddc178ecd25
Source dataset
uspto-grants-2013_06
Patent number
US08455491B2

Reaction notes

Loading…