Dicyclohexylamine → 2-(3,3-Dicyclohexylureido)-4-methylthiazole-5-carboxylic acid (2-hydroxyethyl)amide

HRID 731409

Reaktionsgleichung

Reaktionsgleichung von HRID 731409
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1(N)NC(C)=C[S:8]1)=[O:6].CC(O[Si](C)(C)C)=N[Si](C)(C)C.C1N=CN([C:31]([N:33]2[CH:37]=[N:36][CH:35]=[CH:34]2)=[O:32])C=1.[CH:38]1([NH:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>ClCCl.CN(C1C=CN=CC=1)C>[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:37]([NH:33][C:31]([N:44]([CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[CH:45]2[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]2)=[O:32])=[N:36][C:35]=1[CH3:34])=[O:6]

Komponenten

7

Edukt 4

HCID 7582DicyclohexylamineHCID 25248trimethylsilyl N-trimethylsilylethanimidateHCID 682631,1'-CarbonyldiimidazoleHCID 866301872-Amino-4-methyl-thiazole-carboxylic acid (2-hydroxyethyl)-amide

Produkt 1

HCID 576882882-(3,3-Dicyclohexylureido)-4-methylthiazole-5-carboxylic acid (2-hydroxyethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-4-methyl-thiazole-carboxylic acid (2-hydroxyethyl)-amide (0.2 g) in dichloromethane was added N,O-bis-(trimethylsilyl)-acetamide (0.2 g) and the mixture stirred for 12 h. CDI (0.16 g) and DMAP (6 mg) was then added and the mixture stirred for 12 h before addition of dicyclohexylamine (0.18 g). After stirring overnight waster was added and the aqueous phase extracted with dichloromethane, concentrated and purified by chromatography to give the title compound.

Aufarbeitung

  1. stirringAfter stirring overnight waster
  2. additionwas added
  3. extractionthe aqueous phase extracted with dichloromethane
  4. concentrationconcentrated
  5. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2d4de976a669412394bdef82b98537b3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582769B2

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