Nitrogen → N-(2-methyl-4-(4-methyl-2-propyl-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-2-methylthiazol-5-yl)acetamide	HCID 86715559	—
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-(2-methyl-4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide	HCID 86715560	12.7%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A flask (backfilled with N2) was charged with N-(4-bromo-2-methylthiazol-5-yl)acetamide (400 mg, 1.7 mmol), CuI(324 mg, 1.7 mmol) and Cs2CO3 (1.6 g, 5.1 mmol). Trans-N,N′-dimethylcyclohexane-1,2-diamine (CAS: 61798-24-1, 242 mg, 1.7 mmol) and 4-methyl-2-propyl-1H-imidazole (230 mg, 1.9 mmol) in DMF (9.0 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 was purified by prep-HPLC to give 60 mg of the pure title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388180B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-319d7e8cb8094948b0b3c496ad3cbe0c
Source note	uspto-grants-2016_07