Pyridazine, 3-chloro-, 2-oxide → HCID 178420148, compound

HRID 42320Notes

Reaction equation

HRID 42320 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[NH:16][CH:17]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:25]1[N+:30]([O-])=[N:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O.O>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][N:21]([C:28]5[N:29]=[N:30][CH:25]=[CH:26][CH:27]=5)[CH2:20][CH2:19]4)[NH:16][CH:17]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6403197Pyridazine, 3-chloro-, 2-oxideHCID 178420149HCID 178420149, compound

Product 1

HCID 178420148HCID 178420148, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound is prepared in a similar manner described above using Buchwald-Hartwig amination conditions or as described in PCT International Application 2006/058338, 1 Jun. 2006. In this case, a solution consisting of 2-phenyl-5-(2-(piperidin-4-yl)-1H-imidazol-4-yl)pyrimidine and 6-chloropyridazine 1-oxide (preparation of this reagent can be found in PCT International Application 2007/106670, 20 Sep. 2007 and Chemical and Pharmaceutical Bulletin, 1963, 11, 261-263) in dimethylsulfoxide is heated at 80° C. for 18 hours. The reaction mixture is cooled, diluted with water and the organic material is extracted with ethyl acetate. The organic phase is washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is chromatographed on silica to afford the title compound.

Workup

  1. customThe title compound is prepared in a similar manner
  2. custompreparation of this reagent
  3. temperatureThe reaction mixture is cooled
  4. extractionthe organic material is extracted with ethyl acetate
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-0bbe9b637e8c4aed912e05a10242b34f
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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