Triethylamine → 3,5-Di-t-butyl-N-[2-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]ethyl]-4-hydroxybenzamide hydrochloride

HRID 412373

반응식

HRID 412373 반응식
C(N(CC)CC)C.[ClH:8].Cl.[NH2:10][CH2:11][CH2:12][C:13]1[CH:45]=[CH:44][C:16]([O:17][C:18]2[CH:19]=[CH:20][C:21]3[N:25]=[C:24]([CH2:26][O:27][C:28]4[CH:41]=[CH:40][C:31]([CH2:32][CH:33]5[S:37][C:36](=[O:38])[NH:35][C:34]5=[O:39])=[CH:30][CH:29]=4)[N:23]([CH3:42])[C:22]=3[CH:43]=2)=[CH:15][CH:14]=1.[C:46]([C:50]1[CH:51]=[C:52]([CH:56]=[C:57]([C:60]([CH3:63])([CH3:62])[CH3:61])[C:58]=1[OH:59])[C:53](O)=[O:54])([CH3:49])([CH3:48])[CH3:47].CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[ClH:8].[C:60]([C:57]1[CH:56]=[C:52]([CH:51]=[C:50]([C:46]([CH3:49])([CH3:48])[CH3:47])[C:58]=1[OH:59])[C:53]([NH:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:19]=[CH:20][C:21]3[N:25]=[C:24]([CH2:26][O:27][C:28]4[CH:41]=[CH:40][C:31]([CH2:32][CH:33]5[S:37][C:36](=[O:38])[NH:35][C:34]5=[O:39])=[CH:30][CH:29]=4)[N:23]([CH3:42])[C:22]=3[CH:43]=2)=[CH:44][CH:45]=1)=[O:54])([CH3:63])([CH3:62])[CH3:61]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 865877735-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

생성물 1

HCID 185376693,5-Di-t-butyl-N-[2-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]ethyl]-4-hydroxybenzamide hydrochloride수율 42.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of anhydrous triethylamine (0.106 g), 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.3 g), anhydrous N,N-dimethylformamide (10 ml), 3,5-di-t-butyl-4-hydroxybenzoic acid (0.13 g) and 1-ethyl-3-[(3′-dimethylamino)propyl]carbodiimide hydrochloride (WSC.HCl, 0.13 g) was stirred at room temperature 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 magnesium sulfate and concentrated. The residue was purified by liquid chromatography on a silica gel column using ethyl acetate:n-hexane=4:1 as the eluant. To a solution of the glassy product in ethyl acetate (15 ml) was added 4N hydrogen chloride in 1,4-dioxane (2 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was crystallized in acetone to afford the title compound (0.17 g, pale yellow powder, mp 164-168° C.).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by liquid chromatography on a silica gel column
  7. additionTo a solution of the glassy product in ethyl acetate (15 ml) was added 4N hydrogen chloride in 1,4-dioxane (2 ml)
  8. stirringthe mixture was stirred at room temperature for 30 minutes
  9. concentrationThe reaction mixture was concentrated
  10. customthe residue was crystallized in acetone

출처 및 근거

ORD 기록
ord-e27c539560564c7597bbb2859408e36c
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562849B1

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