Bis-(1H-imidazol-2-YL)-methanone → HCID 178473155, compound

HRID 731466Notes

Reaction equation

HRID 731466 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][S:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][CH:8]=1)[CH3:2].[C:14](C1NC=CN=1)(C1NC=CN=1)=[O:15].[CH:26]1([NH:32][C@H:33]2[CH2:38][CH2:37][C@H:36]([CH2:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:35][CH2:34]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][S:6][C:7]1[S:11][C:10]([NH:12][C:14]([N:32]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C@H:33]2[CH2:34][CH2:35][C@H:36]([CH2:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:37][CH2:38]2)=[O:15])=[N:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 178420520HCID 178420520, compound

Product 1

HCID 178473155HCID 178473155, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (2-amino-thiazol-5-ylsulfanyl)-acetic acid ethyl ester (0.13 g), carbonyl diimidazole (0.11 g) and 4-dimethylaminopyridine (4 mg) in tetrahydrofuran (10 mL) and tetrahydrofuran (10 mL) was stirred at room temperature for 2 h. Cyclohexyl-(trans-4-phenoxymethyl-cyclohexyl)-amine was added and the reaction stirred overnight at room temperature. Purification by flash chromatography gave 80 mg {2-[3-cyclohexyl-3-(trans-4-phenoxymethyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6972bf767fba4be4b9ee1f5b51b63331
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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