Dimethyl Sulfoxide → HCID 57505480, compound

HRID 2391213Notes

Reaction equation

HRID 2391213 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[N:7]=1.[OH:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:34])=[C:22]([NH:24][C:25]([C:27]2[CH:31]([CH3:32])[CH2:30][N:29]([CH3:33])[N:28]=2)=[O:26])[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O.C(OCC)(=O)C.O1CCCC1>[CH:14]1([C:12]([NH:11][C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([O:17][C:18]4[CH:19]=[CH:20][C:21]([CH3:34])=[C:22]([NH:24][C:25]([C:27]5[CH:31]([CH3:32])[CH2:30][N:29]([CH3:33])[N:28]=5)=[O:26])[CH:23]=4)=[N:7][N:6]3[CH:8]=2)=[O:13])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideHCID 57505439HCID 57505439, compound

Product 1

HCID 57505480HCID 57505480, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (300 mg, 0.91 mmol), N-(5-hydroxy-2-methylphenyl)-1,4-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxamide (290 mg, 1.2 mmol), cesium carbonate (600 mg, 1.8 mmol) and dimethyl sulfoxide (2 mL) was stirred at 100° C. for 6 hr. Ethyl acetate/tetrahydrofuran and water were added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×4). 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→100/0) to give the title compound (300 mg, 73%) as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×4)
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0)

Sources & evidence

ORD record
ord-3b76a06209c24021b92a70b01a1abcca
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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