Chloroacetone → 6-Chloro-2-methyl-7-phenyl-imidazo[1,2-b]pyridazine

HRID 876867

Reaction equation

HRID 876867 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:16]1N=NC(N)=[C:18](C2C=CC=CC=2)[CH:17]=1.ClCC(=O)C>O1CCCC1.O>[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:5]2[N:6]([CH:16]=[C:17]([CH3:18])[N:8]=2)[N:7]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 569536546-Chloro-5-phenylpyridazin-3-amineHCID 768487136-Chloro-4-phenylpyridazin-3-amine

Product 1

HCID 866921166-Chloro-2-methyl-7-phenyl-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 6-chloro-5-phenyl-pyridazin-3-yl-amine and 6-Chloro-4-phenyl-pyridazin-3-yl-amine (intermediate example Int-1-0, step 3, 65 g=316 mmol) in 65 mL tetrahydrofurane and 650 mL water was heated with 74.5 g (800 mmol) chloroacetone in analogy to the synthesis of the intermediate example Int-1-0, step 4, for 18 hours at reflux. After the usual work up and purification of the residue by chromatography (Biotage Isolera, Kronlab 8 cm, eluents: dichloromethane/methanol) and subsequent crystallization (methyl-tert.butylether/hexane) 11.69 g (30.4%) of the title compound were obtained.

Workup

  1. temperatureat reflux
  2. customAfter the usual work up and purification of the residue by chromatography (Biotage Isolera, Kronlab 8 cm, eluents: dichloromethane/methanol)
  3. customsubsequent crystallization (methyl-tert.butylether/hexane) 11.69 g (30.4%) of the title compound
  4. customwere obtained

Sources & evidence

ORD record
ord-f31d3977efed4a85b61908caad28f507
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Linked notes

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