Réaction #42112

Équation de réaction

Cs2CO3

acetyl chloride

imide

N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1,3 dimethyl-2-oxo-1,8-naphthyridinyl)acetamide

NaH

acetyl chloride

→

N-[3-chloro-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Solvants

EtOAc

methanol

THF

DMF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with saturated aqueous NaHCO3 solution
2. 2
   AutreThe concentrated residue was purified by flash chromatography on silica gel gradient
3. 3
   Lavageeluted with 0-100% EtOAc in hexane affording the title compound

Mode opératoire

To the product to Step A (100 mg) in THF (1.5 mL) and DMF (0.3 mL) was added NaH (13 mg, 60% dispersion in mineral oil) at 0° C. After about 10 minutes acetyl chloride (61.4 μL) was added. An additional portion of acetyl chloride (30 μL) was added. Analysis of the reaction solution indicated a distribution between the 4-amino, 4-N-acetamide and 4-di-N-acetamide. The imide was cleaved by adding a solution of Cs2CO3 (about 200 mg) in methanol (about 5 mL). The reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and then brine. 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: 506.0 (M+1), 508.0 (M+3); Rt=4.50 min.

Source