Water → (4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597867Notes

Reaction equation

HRID 597867 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[F:12])=[O:4].[Cl:13][C:14]1[N:19]=[N:18][C:17](/[N:20]=[C:21](/N(C)C)\[CH3:22])=[CH:16][CH:15]=1.O>CN(C=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([C:2]2[N:18]3[N:19]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]3=[N:20][C:21]=2[CH3:22])=[O:4])=[C:6]([F:12])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 450810122-Chloro-1-(4-chloro-2-fluorophenyl)ethan-1-oneHCID 178463304HCID 178463304, compound

Product 1

HCID 56954583(4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 2-chloro-1-(4-chloro-2-fluorophenyl)ethanone (1.5 kg, 5.44 mol), and (E)-N′-(6-chloropyridazin-3-yl)-N,N-dimethylacetimidamide (1.19 kg, 5.72 mol) in DMF (10.14 L) and heat at 120° C. for 5 h. After cooling, add water (30 L) and stir to crystallize the product. Collect the product by filtration and rinse the cake with water (2×12 L) and heptanes (2×10 L) then dry under vacuum to obtain title compound. (1.490 kg, 84.44%; mp=160° C., M+=324).

Workup

  1. temperatureAfter cooling
  2. customto crystallize the product
  3. customCollect the product
  4. filtrationby filtration
  5. washrinse the cake with water (2×12 L) and heptanes (2×10 L)
  6. customthen dry under vacuum

Sources & evidence

ORD record
ord-560163145f5b40a887d66e88d8339a74
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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