Water → HCID 131730946, compound

HRID 2035492Notes

Reaction equation

HRID 2035492 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:27][C:28]([NH2:30])=[O:29].C[N+]1([O-])CCOCC1.O>CN(C)C=O.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:21][CH2:22][C:23](=[O:26])[CH2:24][CH2:25]3)=[CH:18][CH:19]=2)[N:10]=[CH:9][C:8]=1[CH2:27][C:28]([NH2:30])=[O:29]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 131730947HCID 131730947, compound

Product 1

HCID 131730946HCID 131730946, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

120 mg of 4-[(3,5-difluorobenzyl)amino]-6-{[4-(4-hydroxypiperidino)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 191) was dissolved in 1.5 mL of N,N-dimethylformamide, to which 78 mg of 4-methylmorpholine N-oxide, 120 mg of molecular sieve 4A powder and 2.8 mg of tetrapropylammonium perruthenate were added, and stirred at room temperature for 30 minutes. Water was added to the reaction mixture, extracted with ethyl acetate, and the extract was washed with saturated saline. After drying on anhydrous sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1), recrystallized in methanol-ether-hexane to obtain 12 mg (10%) of the title compound as a light brown crystalline powder.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialAfter drying on anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  7. customrecrystallized in methanol-ether-hexane

Sources & evidence

ORD record
ord-4df1c100cb324966b1ba34b8e41058ac
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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