Cesium carbonate → N-(4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

Participants

Role	Name	HCID	Charge
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 178440092	HCID 178440092	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide	HCID 86715554	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A flask was charged with 4-methyl-2-propyl-1H-imidazole from example 1.6 (140 mg, 1.13 mmol), Cs2CO3 (1.10 g, 3.39 mmol) and copper (I) iodide (108 mg, 0.56 mmol). A solution of (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (80 mg, 0.56 mmol,) and N-(4-bromothiazol-5-yl)acetamide from example 1.5 (250 mg, 1.13 mmol) in DMF (30 mL) was added under N2. The mixture was heated at 90° C. for overnight. It was concentrated and directly used for the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388180B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-f27bd79f2fd74948aff96873b9580126
Source note	uspto-grants-2016_07