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 448775

Reaktionsgleichung

Reaktionsgleichung von HRID 448775
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-66f633d0d012452ea58b27bc86e5a5e3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481725B2

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