Hydrochloric Acid → 2-Phenyl-6-(4-isopropylpiperazin-1-yl)-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine

HRID 1253599Notes

Reaction equation

HRID 1253599 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:17]3[CH:22]=[CH:21][N:20]=[N:19][CH:18]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[CH:23]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:25])[CH3:24].Cl>C(O)CCCC>[C:11]1([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([N:29]4[CH2:30][CH2:31][N:26]([CH:23]([CH3:25])[CH3:24])[CH2:27][CH2:28]4)=[N:7][N:6]3[C:8]=2[C:17]2[CH:22]=[CH:21][N:20]=[N:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 780131-IsopropylpiperazineHCID 593677046-Chloro-2-phenyl-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine

Product 1

HCID 252047312-Phenyl-6-(4-isopropylpiperazin-1-yl)-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazineYield 83.4%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
150 °C

Procedure

The mixture of 0.45 g (1.5 mmol) of 6-chloro-2-phenyl-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine and 0.38 g (2.9 mmol) of 1-isopropylpiperazine in 6 ml of pentanol is heated in a sealed tube at 150° C. for 2 days. The mixture is cooled and poured into a 1N aqueous solution of hydrochloric acid. This solution is washed with diethyl ether and then basified using an aqueous solution of sodium hydroxide. The product is finally extracted with dichloromethane, and the organic phase is dried over sodium sulfate, filtered and concentrated under reduced pressure. A brown oil is obtained, which is chromatographed on silica gel, elution being carried out with a mixture of aqueous ammonia, methanol and dichloromethane (0.4/4/96), to give 0.50 g of a solid.

Workup

  1. temperatureThe mixture is cooled
  2. washThis solution is washed with diethyl ether
  3. extractionThe product is finally extracted with dichloromethane
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customA brown oil is obtained
  8. customwhich is chromatographed on silica gel, elution
  9. additionbeing carried out with a mixture of aqueous ammonia, methanol and dichloromethane (0.4/4/96)

Sources & evidence

ORD record
ord-3a6fcc3cb82746228633e26326914174
Source dataset
uspto-grants-2013_06
Patent number
US08455491B2

Reaction notes

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