2-Anilino-N-methoxy-N,7-dimethyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridine-5-carboxamide → HCID 9969333, compound

HRID 1839420Notes

Reaction equation

HRID 1839420 reaction equation
[NH:1]([C:8]1[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]2[CH:11]=[C:12]([CH3:25])[N:13]=[C:14]([C:19](N(OC)C)=[O:20])[C:15]=2[C:16](=[O:18])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Mg+].[Br-]>C1COCC1>[C:19]([C:14]1[N:13]=[C:12]([CH3:25])[CH:11]=[C:10]2[C:15]=1[C:16](=[O:18])[CH:17]=[C:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[N:9]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:20])[CH3:32]

Participants

4

Reactant 2

HCID 219481392-Anilino-N-methoxy-N,7-dimethyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridine-5-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 9969333HCID 9969333, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Anilino-N-methoxy-N,7-dimethyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridine-5-carboxamide (60 mg, 0.14 mmol) was suspended in THF (5 mL). To this stirring suspension at 0° C. was added MeMgBr (0.19 mL, 0.56 mmol, 3M in Et2O). The reaction was stirred at room temperature for 6 h and quenched with saturated aqueous NH4Cl, diluted with EtOAc, and washed with brine. The organic layer was collected, dried over Na2SO4, and concentrated in vacuo. The residue was purified by Biotage silica gel chromatography using EtOAc as the eluent to provide 5-acetyl-2-anilino-7-methyl-1-phenyl-1,6-naphthyridin-4(1H)-one as a light yellow solid (34 mg, 66%): LCMS RT: 2.20 min, MH+: 370.4.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage silica gel chromatography

Sources & evidence

ORD record
ord-81d5595c7230488ba83a93676fdb8575
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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