Acetic Anhydride → N-acetyl-N-(3-chloro-7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

HRID 13835Notes

Reaction equation

HRID 13835 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:4](=[O:31])[C:3]=1[Cl:32].[C:33](OC(=O)C)(=[O:35])[CH3:34].[O:40]1CCO[CH2:42][CH2:41]1>CN(C1C=CN=CC=1)C>[C:33]([N:1]([C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH:10]=2)[N:5]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:4](=[O:31])[C:3]=1[Cl:32])[C:41](=[O:40])[CH3:42])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 112259274-amino-3-chloro-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11319308N-acetyl-N-(3-chloro-7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
60 °C

Procedure

To the product of EXAMPLE 61 (70 mg) in 1,4-dioxane (1 mL) was added acetic anhydride (2 mL) and DMAP (25 mg). The reaction was heated to 60° C. After about 1 hour the reaction was cooled to room temperature and quenched with methanol (1 mL) the reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3/1 M aqueous NaOH solution (1:1). The organic layer was dried (Na2SO4). The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-100% EtOAc in hexane affording the title compound. HPLC/MS: 590.0 (M+1), 592.0 (M+3); Rt=4.59 min.

Workup

  1. temperatureAfter about 1 hour the reaction was cooled to room temperature
  2. customquenched with methanol (1 mL) the reaction
  3. additionwas diluted with EtOAc
  4. washwashed with saturated aqueous NaHCO3/1 M aqueous NaOH solution (1:1)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  7. washeluted with 0-100% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-ff87e2bdb2a445ac81b6522e3c139a31
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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