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Potassium Carbonate → 4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole

HRID 2287571
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HRID 2287571 반응식
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:10]=2[N:9]=[C:8]1[CH2:17][CH3:18])=[O:5])[CH3:2].[Cl:19][C:20]1[C:27]([N:28]([CH3:47])[C:29](=[O:46])[CH2:30][NH:31][C:32](=[O:45])[CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:37][CH:36]=2)=[CH:26][CH:25]=[C:24]([Cl:48])[C:21]=1[CH2:22]Br.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:19][C:20]1[C:27]([N:28]([CH3:47])[C:29](=[O:46])[CH2:30][NH:31][C:32](=[O:45])[CH:33]=[CH:34][C:35]2[CH:36]=[CH:37][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:39][CH:40]=2)=[CH:26][CH:25]=[C:24]([Cl:48])[C:21]=1[CH2:22][O:16][C:15]1[C:10]2[N:9]=[C:8]([CH2:17][CH3:18])[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=2[CH:12]=[CH:13][CH:14]=1
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참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 212546631-ethoxycarbonylmethyl-2-ethyl-4-hydroxy-1H-benzimidazoleHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

생성물 1

HCID 536707184-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole
수율 82.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-ethoxycarbonylmethyl-2-ethyl-4-hydroxy-1H-benzimidazole (140 mg) and 2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyl bromide (289 mg) in dimethylformamide (3 ml) was added potassium carbonate (117 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature and then for 2 hours at ambient temperature. To the reaction mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (5% methanol-ethyl acetate) and pulverized with diisopropyl ether to give 4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole (317 mg) as pale yellow solid.

후처리

  1. temperaturecooling
  2. waitfor 2 hours at ambient temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash chromatography (5% methanol-ethyl acetate)

출처 및 근거

ORD 기록
ord-58c83f0a948f4d0483f185b623f5d781
출처 데이터셋
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06083961

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