HCID 10161450, compound → HCID 10227216, compound

HRID 1839169Notes

Reaction equation

HRID 1839169 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:26]=[N:27][C:28]([C:31]([OH:34])([CH3:33])[CH3:32])=[CH:29][CH:30]=3)[CH:20]=2)[CH:9]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].C(Cl)Cl.CO.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:50].[Mg+2]>CCOCC>[CH2:1]([NH:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:26]=[N+:27]([O-:50])[C:28]([C:31]([OH:34])([CH3:32])[CH3:33])=[CH:29][CH:30]=3)[CH:20]=2)[CH:9]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 10161450HCID 10161450, compoundHCID 21226129Dichloromethane methanolHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 10227216HCID 10227216, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of N-isobutyl-1-{3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Example 46 in 13:1 methylene chloride/methanol (33 ml/mmol) at room temperature was added magnesium monoperoxyphthalate hexahydrate (MMPP, 1.1 molareq) and the resulting mixture was stirred at room temperature for 24 hours. The mixture was filtered through a bed of celite and the filtrate was washed with aqueous sodium carbonate, then water and dried. The crude product was chromatographed on silica gel eluting with 8% ethanol in ethyl acetate and the solid obtained was stirred at room temperature in ether for several hours and filtered to afford the title compound as a light pink solid.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. washthe filtrate was washed with aqueous sodium carbonate
  3. dry with materialwater and dried
  4. customThe crude product was chromatographed on silica gel eluting with 8% ethanol in ethyl acetate
  5. customthe solid obtained
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1dbca726f89745d79cb15e13e1ca97d0
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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