1,1'-Carbonyldiimidazole → HCID 489423、化合物

HRID 864435ノート

反応式

HRID 864435 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([OH:25])=O)=[CH:17]2.[CH2:26]([NH:29][C:30]1[C:31]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:27]C>C1COCC1.ClCCl>[CH3:27][CH2:26][NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[N:32][C:31]=1[N:36]1[CH2:41][CH2:40][N:39]([C:23]([C:18]2[NH:19][C:20]3[CH:21]=[CH:22][C:14]([Cl:13])=[CH:15][C:16]=3[CH:17]=2)=[O:25])[CH2:38][CH2:37]1

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 10331071HCID 10331071、化合物

生成物 1

HCID 489423HCID 489423、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1,1'-carbonyldiimidazole (0.42 g) is added to a 20°-25° solution of 5-chloroindole-2-carboxylic acid (I, 0.5 g) in THF (5 ml). After 1 hour of stirring at 20°-25°, the above reaction is added dropwise over 10 minutes via cannula to a -10° (ice/acetone bath) solution of [3-(ethylamino)-2-pyridinyl]piperazine (II, 0.58 g) in THF (5 ml). After 30 minutes of stirring at -10°, the reaction is warmed to 20°-25° and stirring is continued for 5 hours. The reaction is diluted with dichloromethane (50 ml), washed with saturated aqueous sodium bicarbonate (40 ml), water (40 ml) and saline (40 ml). The organic layers are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate is purified by flash column chromatography (50 g silica gel), eluting with ethyl acetate/hexane (1/1). The appropriate fractions are pooled and concentrated to give the title compound, mp 208°-209°; IR (mineral oil) 3200, 2920-3000, 1632, and 1425 cm-1 ; NMR (300 MHz, CDCl3) 9.77, 7.72, 7.60, 7.36, 7.22, 6.97, 6.86, 6.75, 4.23, 4.09, 3.23-3.15, and 1.33 δ; MS (m/e) 383, 178, 176, 162, 150, 148, 137, 134, and 120.

後処理

  1. customthe above reaction
  2. stirringAfter 30 minutes of stirring at -10°
  3. temperaturethe reaction is warmed to 20°-25°
  4. stirringstirring
  5. waitis continued for 5 hours
  6. washwashed with saturated aqueous sodium bicarbonate (40 ml), water (40 ml) and saline (40 ml)
  7. dry with materialThe organic layers are dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate is purified by flash column chromatography (50 g silica gel)
  10. washeluting with ethyl acetate/hexane (1/1)
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-15fc53c6a8464d46afa3782ecbe4698c
出典データセット
uspto-grants-1996_10
特許番号
US05563142

反応ノート

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