Ethylene Glycol → 5-Chloro-N-((1-(4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Ethylene Glycol	HCID 174	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-Methylhomopiperazine	HCID 228349	—
Reactant	5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide	HCID 57640693	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Isopropanol	HCID 3776	—
Product	5-Chloro-N-((1-(4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide	HCID 24991312	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

The mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (4.1, 100 mg, 0.22 mmol), N-methylhomopiperazine (140 μL, 1.1 mmol), CuI (42 mg, 0.22 mmol), ethylene glycol (25 μL, 0.44 mmol), potassium phosphate (93 mg, 0.44 mmol) in 2 mL isopropanol in a sealed tube was stirred for 16 hrs at 120° C. The title compound was isolated directly from the reaction mixture using reverse phase prep HPLC. MS found for C20H23ClN6OS (M+H)+ 431.1, 433.1 (Cl pattern).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696352B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-af34c869982f413cbb10854a30f642af
Source note	uspto-grants-2010_04