1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 73868

Reaktionsgleichung

Reaktionsgleichung von HRID 73868
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([NH:33][C:34]4([C:40]([OH:42])=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:32])=[CH:27][CH:26]=3)[N:24]=2)[CH2:16][CH2:15]1>CN(C)C=O>[CH3:13][N:14]1[CH2:15][CH2:16][N:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:32][C:40](=[O:42])[C:34]5([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]5)[N:33]=4)=[CH:27][CH:26]=3)[N:24]=2)[CH2:18][CH2:19]1

Komponenten

4

Edukt 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576728871-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid

Produkt 1

HCID 576728032-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

450 mg (2.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 910 mg (2.1 mmol) of 1-[[[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid in 20 ml of dimethylformamide. After the mixture was stirred at room temperature for 4 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 577 mg (67%) of the title compound.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5839b8d57dc84214aed68d17053f81ae
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

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