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

HRID 13851
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HRID 13851 반응식
[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[C:29]#[N:30].[C:31](Cl)(=[O:33])[CH3:32].C(N([CH2:40][CH3:41])CC)C.CN(C=[O:46])C>C1COCC1.CCOC(C)=O>[C:31]([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[C:29]#[N:30])[C:40](=[O:46])[CH3:41])(=[O:33])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 111902884-Amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile

생성물 1

HCID 68713944N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-3-cyano-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

시약·촉매·용매

2
HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To the product of EXAMPLE 98 (43 mg) in DMF (0.5 mL) and THF (1 mL) was added acetyl chloride (65 μL) and triethylamine (0.13 mL). The reaction stirred about 4 hours at room temperature before it was diluted with EtOAc. The solution was washed with saturated aqueous NaHCO3 and brine. The solution was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-85% EtOAc in hexane affording N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-3-cyano-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridin-4-yl)acetamide which was subjected to the conditions of EXAMPLE 65 to afford the title compound. HPLC/MS: 496.8 (M+1), 498.8 (M+3); Rt=3.94 min.

후처리

  1. washThe solution was washed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel gradient
  5. washeluted with 0-85% EtOAc in hexane

출처 및 근거

ORD 기록
ord-b69949a2bce742e08d76265b860bdc44
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728141B2

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