Water → HCID 10115569, compound

HRID 1839163Notes

Reaction equation

HRID 1839163 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](SC)=[CH:26][CH:25]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].O.O[O:34][S:35]([O-:37])=O.[K+].O1CCC[CH2:40]1>CO>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([S:35]([CH3:40])(=[O:37])=[O:34])=[CH:26][CH:25]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 10274246HCID 10274246, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10115569HCID 10115569, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N-isopropyl-1-[3-(4-methylthiophenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Example 22 in tetrahydrofuran (24 ml/mmol), methanol (12 ml/mmol), and water (12 ml/mmol), was added oxone (2.24 eq) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was quenched with saturated aqueous sodium bicarbonate and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with 30% ether in methylene chloride to afford the title compound as a white solid.

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. custompartitioned between ethyl acetate and water
  3. customThe crude product from the organic phase was chromatographed on silica gel eluting with 30% ether in methylene chloride

Sources & evidence

ORD record
ord-eb8aad183bbc427eb439467f0b71e0a0
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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