Dimethylformamide → HCID 73741947, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (E)-2-(4-bromophenyl)-3-furan-2-ylacrylic acid (Preparation 9, 4.10 g, 14.0 mmol) and oxalyl chloride (2.5 mL, 28.0 mmol) in anhydrous CH2Cl2 (100 mL) was treated with a catalytic amount of anhydrous DMF (25 μL). The resulting solution was stirred at 20° C. for 4 h, then the solvents were removed under reduced pressure. CH2Cl2 (50 mL) was added to the residue, then the solvents were evaporated off under reduced pressure to give 2-(4-bromophenyl)-3-furan-2-ylacryloyl chloride as a brown solid. A solution of this acid chloride (343 mg, 1.1 mmol) in anhydrous THF (1 mL) was added to a solution of 5-chlorothiazol-2-ylamine hydrochloride (171 mg, 1.0 mmol) and NEt3 (0.56 mL, 4.0 mmol) in anhydrous THF (1 mL). The suspension was stirred for 16 h at 20° C., then the solvents were removed under reduced pressure. The residue was partitioned between CH2Cl2 (10 mL) and saturated aqueous NaHCO3 (5 mL). The organic layer was washed with H2O (5 mL) and brine (5 mL), before being concentrated. The resulting solid was recrystallised from MeOH to furnish the title compound: RTA=4.39 min; m/z (ES+)=410.9 [M+H]+.

Provenance & Evidence