반응 #42119

반응 방정식

NaH

N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-2-methoxy-N-methylacetamide

product

3-Dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one

2-methoxyacetyl chloride

→

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

용매

THF

DMF

반응 조건

후처리

1. 1
   기타After 15 minutes the reaction was quenched with acetic acid (0.2 mL)
2. 2
   workup.ADDITIONThe reaction was diluted with EtOAc
3. 3
   세척washed with saturated aqueous NaHCO3 solution and brine
4. 4
   workup.ADDITIONthe reaction was diluted with EtOAc
5. 5
   세척washed with saturated aqueous NaHCO3 solution and brine
6. 6
   기타The concentrated residue was purified by flash chromatography on silica gel gradient
7. 7
   세척eluted with 0-100% EtOAc in hexane affording the title compound

실험 절차

N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-2-methoxy-N-methylacetamide (368.5 mg, prepared by the reaction of the product of Step A Example 1 with 2-methoxyacetyl chloride using the conditions of EXAMPLE 62 Step A) was combined with THF (5 mL), DMF (0.5 mL) and NaH (48 mg, 60% dispersion in mineral oil). After 15 minutes the reaction was quenched with acetic acid (0.2 mL). The reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine. The concentrated residue was suspended in THF (4 mL), DMF (0.5 mL) and acetyl chloride (0.5 mL). Once LC/MS indicated the acylation was complete, the reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and 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: 502.0 (M+1), 504.00 (M+3); Rt=3.92 min.

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