Potassium Carbonate → 1-[N-(2-methoxybenzyl)acetylamino]-3-(1H-indol-3-yl)-2-[N-(2-((4-cyclohexyl)piperazin-1-yl)acetyl)amino]propane

HRID 380679

Reaktionsgleichung

Reaktionsgleichung von HRID 380679
C1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)CCCCC1.Br[CH2:14][C:15]([NH:17][CH:18]([CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[CH2:19][NH:20][C:21](=[O:32])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][CH2:22][C:21]([NH:20][CH2:19][CH:18]([NH:17][C:15](=[O:16])[CH2:14][N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH:12]1[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:32]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 872981-CyclohexylpiperazineHCID 697369492-[(2-bromo)acetyl]amino-3-(1H-indol-3-yl)1-[N-(2-methoxybenzyl)acetylamino]propane

Produkt 1

HCID 698886761-[N-(2-methoxybenzyl)acetylamino]-3-(1H-indol-3-yl)-2-[N-(2-((4-cyclohexyl)piperazin-1-yl)acetyl)amino]propaneAusbeute 174,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Cyclohexylpiperazine (3.65 g, 22.492 mmoles) was added to a stirring solution of 2-[(2-bromo)acetyl]amino-3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]propane (21.369 mmoles) and powdered potassium carbonate (3.56 g, 25.758 mmols) in methylene chloride under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. The salts were filtered and the solution concentrated to a brown foam on a rotary evaporator. The desired product was purified on a Prep 500 column using a 10 L gradient starting with 100% methylene chloride and ending with 5% methanol/94.5% methylene chloride/0.5% ammonium hydroxide. Impure fractions were combined and purified further by reverse phase preparative high performance liquid chromatography (methanol/acetonitrile/water/ammonium acetate). After combining the material from both chromatographic purifications the title compound (10.43 g, 18.663 mmoles) was isolated (87% yield).

Aufarbeitung

  1. filtrationThe salts were filtered
  2. concentrationthe solution concentrated to a brown foam on a rotary evaporator
  3. customThe desired product was purified on a Prep 500 column
  4. custompurified further by reverse phase preparative high performance liquid chromatography (methanol/acetonitrile/water/ammonium acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d066a535dc2a47f9a2b5a9fe58bb0372
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303610B1

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