Hydrogen Peroxide → HCID 10000776, compound

HRID 2376637Notes

Reaction equation

HRID 2376637 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]3)[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1.[OH:28]O>CO.O.Cl>[CH3:1][S:2]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([N:19]3[CH2:20][CH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]3)[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1)=[O:28]

Participants

6

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 10091127HCID 10091127, compound

Product 1

HCID 10000776HCID 10000776, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Example 41 (1-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-piperidine-4-carboxylic acid) (30 mg, 0.07 mmol) is dissolved in methanol (200 μl), and hydrogen peroxide (11.1 μl) is added at room temperature. After 3 hours a further amount of hydrogen peroxide (15 μl) is added and the reaction mixture stirred at 45° C. overnight. The mixture is then cooled to room temperature, diluted with water and acidified with 7 M HCl (1 drop). The reaction mixture is extracted into ethyl acetate, which is washed with water and brine. The organic layer is then dried over magnesium sulfate and concentrated to give the product as an amorphous solid. MS (ES+) 396.1308

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. extractionThe reaction mixture is extracted into ethyl acetate, which
  3. washis washed with water and brine
  4. dry with materialThe organic layer is then dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1bc228ab0ed7422db2c9f495225b6252
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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