Sodium hydride → N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)-2-methoxyacetamide

HRID 13811

Reaction equation

HRID 13811 reaction equation
[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2].[H-].[Na+].[CH3:34][O:35][CH2:36][C:37](Cl)=[O:38]>C1COCC1>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH:14][C:37](=[O:38])[CH2:36][O:35][CH3:34])=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11318758N-(3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 2 (100 mg) in THF (3 mL), under nitrogen, was treated with sodium hydride (60% in mineral oil) (10 mg). The suspension was stirred for 5 min were upon methoxyacetyl chloride (40 uL) was added. The reaction was allowed to warm to room temperature and was stirred 30 min. The reaction mixture was quenched with aqueous NaHCO3 (saturated) and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluted with 0-30% EtOAc in hexane afforded the title compound. HPLC/MS: 543.8 (M+1), 545.8 (M+3); Rt=4.19 min.

Workup

  1. additionwas added
  2. stirringwas stirred 30 min
  3. customThe reaction mixture was quenched with aqueous NaHCO3 (saturated)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica
  9. washeluted with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-681d7da1a15142d5a009ebb5f2d80216
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Linked notes

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