5-Methoxyindole-2-carboxylic acid → HCID 489420, 화합물

HRID 2395786노트

반응식

HRID 2395786 반응식
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([OH:26])=O)=[CH:18]2.C(N[C:31]1[C:32]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=N[CH:34]=[CH:35][CH:36]=1)CC.[C:43](=O)(O)[O-:44].[Na+]>O1CCCC1.CCOCC>[CH3:11][CH2:12][O:44][C:43]1[C:32]([N:37]2[CH2:38][CH2:39][N:40]([C:24]([C:19]3[NH:20][C:21]4[CH:22]=[CH:23][C:15]([O:14][CH3:13])=[CH:16][C:17]=4[CH:18]=3)=[O:26])[CH2:41][CH2:42]2)=[CH:31][CH:36]=[CH:35][CH:34]=1

참가 물질

7

반응물 4

HCID 204015-Methoxyindole-2-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 10331071HCID 10331071, 화합물

생성물 1

HCID 489420HCID 489420, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

1,1'-Carbonyldiimidazole (1.30 g) is added to a 20°-25° solution of 5-methoxyindole-2-carboxylic acid (I, 1.39) in tetrahydrofuran (14 ml). The reaction is stirred one hour, then cooled to 0° and 1-(2-ethoxyphenyl)piperazine (II, 1.50 g) dissolved in tetrahydrofuran (7 ml) is added via cannula. The reaction is warmed to 20°-25° and stirred 48 hours. The reaction is diluted with ether (100 ml), poured into saturated aqueous sodium bicarbonate (100 ml). The organic layers are separated and washed with saline (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from toluene to give the title compound, mp 105°-107°.

후처리

  1. temperaturecooled to 0°
  2. additionis added via cannula
  3. temperatureThe reaction is warmed to 20°-25°
  4. stirringstirred 48 hours
  5. customThe organic layers are separated
  6. washwashed with saline (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from toluene

출처 및 근거

ORD 기록
ord-408ec4260d9848dcba9d77df25e256c9
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05489593

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