Dimethylformamide → HCID 73741947, compound

Temperature

20 °C

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 g, 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]+.

1. customthe solvents were removed under reduced pressure
2. additionCH2Cl2 (50 mL) was added to the residue
3. customthe solvents were evaporated off under reduced pressure

ORD record

ord-4a8aa76c7852444da31953710d76a3af

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582632B2