Nitrogen → N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	N-(4-bromo-1,3-thiazol-5-yl)acetamide	HCID 83680500	—
Reactant	HCID 178418800	HCID 178418800	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide	HCID 86715562	20%

Reaction Conditions

Temperature	90 °C

Reaction Steps

N-(4-bromothiazol-5-yl)acetamide from example 1.5 (1 g, 4.52 mmol), CuI(869 mg, 4.52 mmol) and Cs2CO3 (2.9 g, 9.1 mmol) were combined in a flask (backfilled with N2). Trans-N,N′-dimethylcyclohexane-1,2-diamine (630 mg, 4.52 mmol) and 4-methyl-1H-imidazole (446 mg, 5.4 mmol) in DMF (10 mL) were added and the mixture was stirred at 90° C. overnight. After the mixture was cooled to room temperature, the mixture was filtered through a syringe filter (washed with DMF). The filtrate purified by prep-HPLC to give 200 mg of the pure title compound (yield: 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388180B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-1c126b5a271f4efb965b436cc685d891
Source note	uspto-grants-2016_07