Water → HCID 68421251, compound

HRID 501023Notes

Reaction equation

HRID 501023 reaction equation
Cl[CH:2]([C:7](=O)[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[C:19]1[CH:24]=[C:23]([CH3:25])[N:22]=[N:21][C:20]=1[NH2:26].O>CN(C)C=O>[CH3:6][O:5][C:3]([C:2]1[N:21]2[N:22]=[C:23]([CH3:25])[CH:24]=[C:19]([C:13]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=3[CH3:11])[C:20]2=[N:26][C:7]=1[CH2:8][CH3:9])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 545096Methyl 2-chloro-3-oxopentanoateHCID 22024525HCID 22024525, compound

Product 1

HCID 68421251HCID 68421251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 2-chloro-3-oxopentanoate (7 mL) was added to a solution of the resulting 4-(2,4-dimethylphenyl)-6-methyl-3-pyridazinamine in N,N-dimethylformamide (60 mL), and the mixture was heated at 140° C. for 6 hours. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried-over anhydrous magnesium sulfate and evaporated, to give 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazine-3-carboxylic acid methyl ester as a crude product.

Workup

  1. extractionwhich was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried-over anhydrous magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-8fbeb370139b46eea405eee2e0879515
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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