2-(trifluoromethyl)benzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the general method as outlined for Intermediate 2, starting from 2,3-dichloropyrazine and 2-(trifluoromethyl)benzenesulfonamide, the title compound was isolated, after evaporation and recrystallization, as a yellowish solid in 63% yield (97% purity by HPLC).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(trifluoromethyl)benzenesulfonyl chloride (5 g; 20.44 mmol; 1.00 eq.) in anhydrous THF (5.00 ml) was added a solution of 71 ml Ammonia in Ethanol 2M under nitrogen at room temperature. The reaction mixture was shaken for 20 h at room temperature. The solvent was evaporated and the residue redissolved in EtOAc (150 mL) and then washed with NH4Cl saturated aqueous solution (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and the solvent evaporated to give the pure 2-(trifluoromethyl)benzenesulfonamide as a yellowish solid (4.6 g, 89% yield, 98.6% HPLC purity). This compound was utilized as such for the next reaction. The solvent was evaporated the residue redissolved in EtOAc (150 mL) washed with NH4Cl saturated aqueous solution (50 mL) and brine (50 mL) The organic layer was dried over MgSO4 filtered the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by coupling 1a and 2-(trifluoromethyl) benzenesulfonamide (Synlett, 1997, 375) in accordance with Procedure 1, Method B described hereinabove. Yield (14%); 1H NMR (d6-DMSO) δ 12.49 (br s, 1H), 7.98-7.90 (m, 3H), 7.39-7.08 (m, 13H), 6.85 (d, J=8.0 Hz, 2H), 6.47 (d, J=15.7 Hz, 1H), 2.36 (q, J=7.3 Hz, 2H), 0.82 (t, J=7.3 Hz, 3H); APcI m/z: 562 (M+H+) Prepared Yield (14%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by coupling 1a and 2-(trifluoromethyl) benzenesulfonamide (Synlett, 1997, 375) in accordance with Procedure 1, Method B described hereinabove. Yield (14%); 1H NMR (d6-DMSO) δ 12.49 (br s, 1H), 7.98-7.90 (m, 3H), 7.39-7.08 (m, 13H), 6.85 (d, J=8.0 Hz, 2H), 6.47 (d, J=15.7 Hz, 1H), 2.36 (q, J=7.3 Hz, 2H), 0.82 (t, J=7.3 Hz, 3H); APcI m/z: 562 (M+H+) Prepared Yield (14%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by coupling 1a and 2-(trifluoromethyl)-benzenesulfonamide (Synlett, 1997, 375) in accordance with Procedure 1, Method B described hereinabove. Yield (14%); 1H NMR (d6-DMSO) δ 12.49 (br s, 1H), 7.98–7.90 (m, 3H), 7.39–7.08 (m, 13H), 6.85 (d, J=8.0 Hz, 2H), 6.47 (d, J=15.7 Hz, 1H), 2.36 (q, J=7.3 Hz, 2H), 0.82 (t, J=7.3 Hz, 3H); APcI m/z: 562 (M+H+). Prepared Yield (14%)