Naphthyridinone → 9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-2,4,4,6-tetramethyl-4,6-dihydro-5H-[1,3]oxazino[5,4-c]-1,8-naphthyridin-5-one

HRID 13807

Reaction equation

HRID 13807 reaction equation
[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH:14][C:15](=O)[CH3:16])=[CH:11][C:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2].[CH3:35][Mg+].[Br-]>C1COCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:10]2[C:9]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])=[N:8][C:7]3[N:6]([CH3:33])[C:5](=[O:34])[C:4]4[C:1]([CH3:2])([CH3:35])[O:3][C:15]([CH3:16])=[N:14][C:13]=4[C:12]=3[CH:11]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 11386747NaphthyridinoneHCID 178418689HCID 178418689, compound

Product 1

HCID 113642689-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-2,4,4,6-tetramethyl-4,6-dihydro-5H-[1,3]oxazino[5,4-c]-1,8-naphthyridin-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product of Example 1 (59.5 mg) in THF (2 mL) at 0° C. was added 0.52 mL MeMgBr solution (1.4 M, 75% toluene/25% THF). After 10 min the reaction was quenched with saturated aqueous NH4Cl and then diluted with EtOAc. The solution was washed with 10% aqueous NaHSO4 followed by aqueous NaHCO3/NaOH (4:1) before drying (Na2SO4). The concentrated residue was purified by preparative TLC (silica gel) eluted with 15% EtOAc in hexane affording the title compound. HPLC/MS: 512.0 (M+1), 514.0 (M+3); Rt=5.14 min.

Workup

  1. customAfter 10 min the reaction was quenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe solution was washed with 10% aqueous NaHSO4
  4. dry with materialbefore drying (Na2SO4)
  5. customThe concentrated residue was purified by preparative TLC (silica gel)
  6. washeluted with 15% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-1c35074f7fe847f8b31359431c209c52
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Linked notes

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