1,2-Diaminocyclohexane, trans- → 5-Chloro-N-((1-(4-(2-oxo-tetrahydropyrimidin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2(1H)-Pyrimidinone, tetrahydro-	HCID 74615	—
Reactant	5-Chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24986897	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-Chloro-N-((1-(4-(2-oxo-tetrahydropyrimidin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24760093	5.3%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 prepared in Example 1 (80 mg, 0.18 mmol), tetrahydro-2-pyrimidinone (54 mg, 0.54 mmol), 1,2-trans-diaminocyclohexane (13 μL, 0.11 mmol) and K3PO4 (100 mg, 0.47 mmol) in dioxane (1 mL) was degassed with Ar before being charged with CuI (20 mg, 0.11 mmol). The mixture in a sealed tube was heated at 110° C. overnight. It was then purified by HPLC to give the title compound (4 mg). MS 416.1 and 418.1 (M+H, Cl pattern).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08063077B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-48dc8b3e658e40d384deaa72515ab0ca
Source note	uspto-grants-2011_11