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

HRID 731409

Reaction equation

HRID 731409 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-2d4de976a669412394bdef82b98537b3
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Linked notes

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