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

HRID 13840Notes

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]([CH3:27])[C:4](=[O:28])[C:3]=1[N:29]([CH3:31])[CH3:30].[C:32](OC(=O)C)(=[O:34])[CH3:33].[O:39]1CCO[CH2:41][CH2:40]1>CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:32]([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]([CH3:27])[C:4](=[O:28])[C:3]=1[N:29]([CH3:31])[CH3:30])[C:40](=[O:39])[CH3:41])(=[O:34])[CH3:33]

Participants

Conditions

Temperature: 105 °C

Procedure

To the product of EXAMPLE 72 (48.8 mg) in 1,4-dioxane (1 mL) was added acetic anhydride (2 mL) and DMAP (20 mg). The reaction was heated to 105° C. After about 1 hour the reaction was cooled to room temperature and diluted with EtOAc. The solution 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: 557.1 (M+1), 559.1 (M+3); Rt=4.40 min.

Workup

temperatureAfter about 1 hour the reaction was cooled to room temperature
washThe solution washed with saturated aqueous NaHCO3/1 M aqueous NaOH solution (1:1)
dry with materialThe organic layer was dried (Na2SO4)
customThe concentrated residue was purified by flash chromatography on silica gel gradient
washeluted with 0-100% EtOAc in hexane affording the title compound

Sources & evidence

ORD record: ord-4140ec28afeb4a8e8b1a008adda1825e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728141B2

Reaction notes

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