Dimethylformamide → HCID 66695753, compound

HRID 1773653Notes

Reaction equation

HRID 1773653 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=5)[CH:19]=[C:20](SC)[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:31])[CH2:3][CH2:2]1.O[O:34][S:35]([O-:37])=O.[K+].[CH3:39]N(C=O)C>>[CH:1]1([NH:4][C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=5)[CH:19]=[C:20]([S:35]([CH3:39])(=[O:37])=[O:34])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:31])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 23707502Potassium hydroxy sulfite2×HCID 66693894HCID 66693894, compound

Product 1

HCID 66695753HCID 66695753, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4.96 g (11.06 mmol) N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(methylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide which was prepared according to intermediate example 486b in DMF (250 mL) were added 20.4 g (33.18 mmol) oxone in one portion at rt. After reaction for 72 h, further 30 g (55 mmol) oxone are added and the mixture is heated at 70° C. for one hour. Extraction with ethyl acetate/water, filtration of the organic phase through a Whatman filter and evaporation of the organic phase yielded the crude product (4.96 g, 93%) which was used without further purification.

Workup

  1. customAfter reaction for 72 h
  2. extractionExtraction
  3. filtrationwith ethyl acetate/water, filtration of the organic phase through a Whatman
  4. filtrationfilter
  5. customevaporation of the organic phase

Sources & evidence

ORD record
ord-89ba40aa77ee467e87e502affb9f25f8
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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