Methyl iodide → N-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N-methylacetamide

HRID 13810

반응식

HRID 13810 반응식
[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2].IC.[C:34]([O-])([O-])=O.[Cs+].[Cs+].C1C[O:43][CH2:42][CH2:41]1>>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[N:14]([CH3:34])[C:42](=[O:43])[CH3:41])=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2]

참가 물질

5

반응물 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

생성물 1

HCID 11341526N-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N-methylacetamide

실험 절차

A solution of the product from Example 2 (60 mg) in THF (1 mL), under nitrogen, was treated with iodomethane (73 uL) and Cs2CO3 (58 mg). The suspension was stirred overnight. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 25% EtOAc in hexane afforded the title compound. HPLC/MS: 528.1 (M+1), 530.1 (M+3); Rt=4.08 min.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on a preparative silica TLC plate
  7. washeluted with 25% EtOAc in hexane

출처 및 근거

ORD 기록
ord-5eb9e7fa91e14297917b7a7df98dfbc3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728141B2

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