1,2-Diaminocyclohexane, trans- → 5-Chloro-N-((1-(4-(3-oxothiomorpholino)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Edukt	Potassium Phosphate, Tribasic	HCID 62657	—
Edukt	1,4-Tetrahydrothiazine-3-one	HCID 88402	—
Edukt	5-Chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24986897	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Lösungsmittel	1,4-Dioxane	HCID 31275	—
Produkt	5-Chloro-N-((1-(4-(3-oxothiomorpholino)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24760026	25,9%

Reaktionsbedingungen

Temperatur	110 °C

Reaktionsschritte

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 prepared in Example 1 (230 mg, 0.518 mmol), 3-thiomorpholinone (121 mg, 1.03 mmol), 1,2-trans-diaminocyclohexane (26 μL, 0.21 mmol) and K3PO4 (220 mg, 1.04 mmol) in dioxane (2 mL) was degassed with Ar before being charged with CuI (40 mg, 0.21 mmol). The mixture in a sealed tube was heated at 110° C. overnight. It was then purified by HPLC to give the title compound (58 mg). MS 433.1 and 435.0 (M+H, Cl pattern).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08063077B2
Quelldatensatz	uspto-grants-2011_11
ORD ID	ord-0fcc159be8a44d58bc0116013f19138d
Quellennotiz	uspto-grants-2011_11