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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 636495
ノート
印刷プレビュー

反応式

HRID 636495 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-315f9320b48c4ad9b825360a1c2c67a8
出典データセット
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06194396B1

反応ノート

読み込み中…

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