Ethylene Glycol → 5-Chloro-N-((1-(4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1H-pyrazol-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-pyrazol-4-yl)methyl)thiophene-2-carboxamide	HCID 68510993	—
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-pyrazol-4-yl)methyl)thiophene-2-carboxamide	HCID 59260096	5.2%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide (100 mg, 0.225 mmol), 1-methylhomopiperazine (0.100 mL, 0.81 mmol), ethylene glycol (0.025 mL, 0.45 mmol) and K3PO4 (100 mg, 0.47 mmol) in isopropanol (1 mL) was degassed with Argon before being charged with CuI (20 mg, 0.11 mmol). The mixture in a sealed tube was heated at 85° C. overnight. It was then purified by HPLC to give the title compound (5 mg). MS 430.0 and 432.0 (M+H, Cl pattern).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696352B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-349fcdd75512491688e12c4a6f3b7425
Source note	uspto-grants-2010_04