HCID 17989739, compound → HCID 10200674, compound

HRID 917321Notes

Reaction equation

HRID 917321 reaction equation
OOS([O-])=O.[K+].[CH3:7][S:8]([C:11]1[CH:12]=[C:13]([C:17]2[N:18]=[C:19]([CH:27]3[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]3)[CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)[CH:14]=[CH:15][CH:16]=1)(=O)=[O:9]>C1COCC1.O.C(OCC)(=O)C.O>[CH3:7][S:8]([C:11]1[CH:12]=[C:13]([C:17]2[N:18]=[C:19]([CH:27]3[CH2:28][CH2:29][CH:30]([C:33]([OH:35])=[O:34])[CH2:31][CH2:32]3)[CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)[CH:14]=[CH:15][CH:16]=1)=[O:9]

Participants

6

Reactant 2

HCID 17989739HCID 17989739, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 10200674HCID 10200674, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 4-[8-(3-Methanesulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid (30 mg, 0.079 mmol) in THF (1.4 ml) is cooled in a salt/ice bath and oxone (14.5 mg, 0.024 mmol) in water (0.5 ml) is added. After 15 minutes the reaction mixture is allowed to warm to room temperature and after a further 30 minutes more oxone (14.5 mg is added). The mixture is diluted with ethyl acetate/water and the aqueous layer extracted with ethyl acetate. The combined organic layers are washed with brine then dried over magnesium sulfate. Filtration followed by evaporation yields a foam consisting of title compound and 4-[8-(3-Methanesulfonyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid. MS (AP+) 395.87

Workup

  1. additionis added
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation
  7. customyields a foam

Sources & evidence

ORD record
ord-d6385ac8f7454dadb4a9b0906d3d92c4
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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