Dimethylformamide → HCID 10273888, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing the 6-bromo-N-(4-chlorobenzyl)-1-methyl-1H-thieno[2,3-e]-[1,3,4]thiadiazine-3-carboxamide 4,4-dioxide (Preparation 57, 0.19 g), DMF (6 mL), and triethylamine (0.8 mL) is degassed by evacuation under house vacuum and filling with nitrogen 3 times. To this solution is added propargyl alcohol (24 μL), palladium(II)chloride bistriphenylphosphine (8 mg), and copper(I)iodide (14 mg). The mixture is warmed to 65° C. After cooling, the reaction mixture is concentrated under a stream of nitrogen and the resulting residue is partitioned between CH2Cl2 and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated to give a brown oil. The crude product is chromatographed on a Biotage column eluting with 60% ethyl acetate in heptane (200 mL), 80% ethyl acetate in heptane (200 mL), and ethyl acetate (500 mL) followed by purification by radial chromatography eluting with CH2Cl2 to give 40 mg (25%) of the title compound as a pale yellow solid. Physical characteristics: M.p. 98° C. (dec); MS (ESI+) m/z 446 (M+Na)+; HRMS (FAB) m/z 424.0191 (C17H14ClN3O4S2+H).

Provenance & Evidence