Diethyl Ether → 1-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid

HRID 73867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73867
[OH-].[Na+].C1(C[O:10][C:11]([C:13]2([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:29]=[C:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[S:31][CH:32]=4)=[CH:24][CH:23]=3)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])C=CC=CC=1.CCOCC>O1CCCC1>[CH3:39][N:36]1[CH2:35][CH2:34][N:33]([C:30]2[S:31][CH:32]=[C:28]([C:25]3[CH:24]=[CH:23][C:22]([C:20]([NH:19][C:13]4([C:11]([OH:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:21])=[CH:27][CH:26]=3)[N:29]=2)[CH2:38][CH2:37]1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 576728201-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

Produkt 1

HCID 576728871-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acidAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

35 ml of 2N aqueous sodium hydroxide solution was added to a solution of 11.8 g (23.0 mmol) of 1-[[[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester in 120 ml of tetrahydrofuran, and the mixture was heated under reflux for 15 hours. Ether was added to the reaction solution to separate the aqueous layer. Concentrated hydrochloric acid was added to the separated aqueous layer to neutralize it, and the precipitated crystal was collected by filtration to obtain 6.60 g (67%) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. customto separate the aqueous layer
  4. additionConcentrated hydrochloric acid was added to the separated aqueous layer
  5. filtrationthe precipitated crystal was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6d06b5e3cdf247b2bb02564b6c2bcee9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

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