Potassium Carbonate → HCID 57505640, compound

HRID 1668090Notes

Reaction equation

HRID 1668090 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].I[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[N:21]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:25]1([C:23]([NH:22][C:20]2[N:21]=[C:16]3[CH:15]=[CH:14][C:13]([S:1][C:2]4[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=4[C:4]([O:6][CH3:7])=[O:5])=[N:18][N:17]3[CH:19]=2)=[O:24])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 57505640HCID 57505640, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-mercaptobenzoate (1030 mg, 6.1 mmol), N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (1.0 g, 3.1 mmol), potassium carbonate (1050 mg, 7.6 mmol) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 7 hr. The mixture was evaporated under reduced pressure, and ethyl acetate/tetrahydrofuran and water were added to the residue. The aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→90/10) to give methyl 2-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}thio)benzoate (200 mg, 18%) as a brown solid.

Workup

  1. customThe mixture was evaporated under reduced pressure, and ethyl acetate/tetrahydrofuran and water
  2. additionwere added to the residue
  3. extractionThe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  4. washCombined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→90/10)

Sources & evidence

ORD record
ord-6bb0c33ca84e45808eb5975f66033529
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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