1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118113929, compound

Participants

Reaction Steps

Hydroxybenzotriazole (109 mg, 0.81 mmol), N,N-diisopropylethylamine (0.23 ml, 1.34 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (155 mg, 0.81 mmol) were sequentially added to a the solution of 2-bromoimidazo[2,1-b]thiazole-6-carboxylic acid (supplied by Chemizon, 200 mg, 0.81 mmol) in a solvent mixture of methylene chloride (5 ml) and N,N-dimethyl formamide (2 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. After the addition of (4-(tert-butyl)phenyl)methanamine (0.42 ml, 2.78 mmol) at room temperature, the reaction mixture was stirred at room temperature for 24 hours, then diluted with methylene chloride. The reaction mixture was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride. The combined organic layer was washed with brine, then dried over anhydrous magnesium sulfate. After concentration, water was added to the residue. Filtration, followed by drying in vacuo, gave the title compound, 2-bromo-N-(4-(tert-butyl)benzyl)imidazo[2,1-b]thiazole-6-carboxamide, as a solid (148 mg, 87% yield).

Provenance & Evidence