2,6-Diisopropylphenyl isocyanate → 1-(2,6-Diisopropylphenyl)-3-[7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6yloxy]naphthalen-1-yl)urea

HRID 412356노트

반응식

HRID 412356 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12][C:13]1[CH:14]=[CH:15][C:16]3[N:20]=[C:19]([CH2:21][O:22][C:23]4[CH:36]=[CH:35][C:26]([CH2:27][CH:28]5[S:32][C:31](=[O:33])[NH:30][C:29]5=[O:34])=[CH:25][CH:24]=4)[N:18]([CH3:37])[C:17]=3[CH:38]=1)[CH:8]=[CH:7]2.[CH:39]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:50])[CH3:49])[C:43]=1[N:51]=[C:52]=[O:53])([CH3:41])[CH3:40]>CN(C)C=O>[CH:39]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:49])[CH3:50])[C:43]=1[NH:51][C:52]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]3[CH:14]=[CH:15][C:16]4[N:20]=[C:19]([CH2:21][O:22][C:23]5[CH:24]=[CH:25][C:26]([CH2:27][CH:28]6[S:32][C:31](=[O:33])[NH:30][C:29]6=[O:34])=[CH:35][CH:36]=5)[N:18]([CH3:37])[C:17]=4[CH:38]=3)[CH:10]=2)[CH:5]=[CH:4][CH:3]=1)=[O:53])([CH3:40])[CH3:41]

참가 물질

4

반응물 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 98327115-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione

생성물 1

HCID 101469331-(2,6-Diisopropylphenyl)-3-[7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6yloxy]naphthalen-1-yl)urea수율 34.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 5-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.5 g) and N,N-dimethylformamide (10 ml) was added 2,6-diisopropylphenyl isocyanate (0.20 g) and the mixture was allowed to stand at room temperature for 5 days. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3/2→3/1 as the eluant. The product was recrystallized from methanol to afford the title compound (0.24 g, mp 164-169° C.).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe extract was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column
  6. customThe product was recrystallized from methanol

출처 및 근거

ORD 기록
ord-5949e50b9c77492c917655cbae0eeb43
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562849B1

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