Theophylline → 7-[4-(6-Chloronicotinoyl)benzyl]-1,3-dimethylxanthine

HRID 1291416노트

반응식

HRID 1291416 반응식
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1>CN(C=O)C.O>[Cl:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31][N:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:13])[C:6]=4[N:7]=[CH:8]3)=[CH:29][CH:28]=2)=[O:26])=[CH:23][N:22]=1

참가 물질

6

반응물 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 189188004-(6-Chloronicotinoyl)benzyl bromide

생성물 1

HCID 189188457-[4-(6-Chloronicotinoyl)benzyl]-1,3-dimethylxanthine수율 96.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 1,3-dimethylxanthine (712 mg), potassium carbonate (578 mg) and 4-(6-chloronicotinoyl)benzyl bromide (1515 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and. concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:3) and recrystallized from chloroform-isopropyl ether to provide the title compound as colorless solid (1562 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:3)
  6. customrecrystallized from chloroform-isopropyl ether

출처 및 근거

ORD 기록
ord-3be66d59852e4620ac6d8e241149b10e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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