Dimethylformamide → 1-(Adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)urea

HRID 412334

反応式

HRID 412334 の反応式
Cl.Cl.[NH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][CH:5]=1.[C:37]12([N:47]=[C:48]=S)[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2.C(N(CC)CC)C.CN(C)C=[O:60]>>[C:37]12([NH:47][C:48]([NH:3][C:4]3[CH:36]=[CH:35][C:7]([O:8][C:9]4[CH:10]=[CH:11][C:12]5[N:16]=[C:15]([CH2:17][O:18][C:19]6[CH:32]=[CH:31][C:22]([CH2:23][CH:24]7[S:28][C:27](=[O:29])[NH:26][C:25]7=[O:30])=[CH:21][CH:20]=6)[N:14]([CH3:33])[C:13]=5[CH:34]=4)=[CH:6][CH:5]=3)=[O:60])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 107279Adamantyl isothiocyanateHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

生成物 1

HCID 101223331-(Adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)urea

反応条件

温度
50 °C

実験手順

A mixture of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), 1-adamantyl isothiocyanate (284 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 4.5 hours, at 50° C. for 2.5 hours and then at 80° C. for 4.5 hours. The reaction mixture was concentrated and 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=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate to afford the title compound (192 mg, mp 164.0-166.6° C.).

後処理

  1. waitat 80° C. for 4.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. customn-hexane=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-55abd78f2e8243ba8bb97b31de87291e
出典データセット
uspto-grants-2003_05
特許番号
US06562849B1

関連ノート

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