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Diisopropylamine → 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

HRID 278035
ノート
印刷プレビュー

反応式

HRID 278035 の反応式
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH2:15])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([C:31](O)=[O:32])=[CH:30][C:24]=3[N:23]=2)=[CH:18][CH:17]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(NC(C)C)(C)C>CN(C)C=O>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH:15][C:31]([C:29]1[CH:28]=[CH:27][C:25]2[NH:26][C:22]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[N:23][C:24]=2[CH:30]=1)=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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 7912DiisopropylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 697111551-[1,3,4]Oxadiazole-2-yl-3-phenylpropylamineHCID 178524160HCID 178524160、化合物

生成物 1

HCID 1785232812-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

220 mg of 1-[1,3,4]oxadiazole-2-yl-3-phenylpropylamine were dissolved in 10 ml of dry dimethylformamide at RT, treated with 260 mg of 2-pyridin-4-yl-1H-benzimidazol-5-carboxylic acid, 350 mg of TOTU, and 0.15 ml of diisopropylamine, and stirred at RT for 4 h. The reaction mixture was concentrated, the residue was taken up in ethyl acetate, and the mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel using dichloromethane/methanol (8/1) and yielded 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide, which melts at 103° C. with decomposition.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. washthe mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-3026923cd43a4aef8ee7c8a1e3428a01
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06358978B1

反応ノート

読み込み中…

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