Tetrahydrofuran → HCID 9969334, compound

HRID 2215022Notes

Reaction equation

HRID 2215022 reaction equation
[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[N:15]=[C:14]([C:24](N(OC)C)=[O:25])[CH:13]=C(C)C=2C(=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Mg+].[Br-].[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1>>[C:24]([C:14]1[N:15]=[C:16]2[C:36]([C:37](=[O:38])[CH:9]=[C:8]([NH:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:17]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:35]([CH3:39])[CH:13]=1)(=[O:25])[CH3:32]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21948200HCID 21948200, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 9969334HCID 9969334, compoundYield 74%

Procedure

To a suspension of 7-anilino-N-methoxy-N,4-dimethyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxamide (100 mg, 0.24 mmol) in THF (5 mL) at 0° C. was added MeMgBr (3M in Et2O, 322 uL, 0.97 mmol). The suspension became a red solution. As the reaction proceeded the solution lost its red color. After 1 h the reaction was quenched with saturated NH4Cl, diluted with EtOAc, and washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by a Biotage silica gel chromatography using EtOAc to afford 7-acetyl-2-anilino-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one as a light yellow solid (65 mg, 74%): LCMS RT: 2.63 min, MH+: 370.4.

Workup

  1. customAfter 1 h the reaction was quenched with saturated NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by a Biotage silica gel chromatography

Sources & evidence

ORD record
ord-fc588f08194748b49b633dc77f8cee3c
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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