3-chloro-2-methylbenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 16.4 gm (80 mmols) of 3-chloro-2-methyl-benzene sulfonamide, 14 gm (100 mmols) of potassium carbonate, 33.2 gm (210 mmols) of potassium permanganate and 350 ml of water was refluxed for 1 hour. The reaction mixture was filtered while still hot, and the filter cake was washed with hot water. The combined filtrates were acidified with concentrated aqueous hydrochloric acid and cooled. The resulting crystals were suction-filtered off, washed with water and dried. was refluxed for 1 hour The reaction mixture was filtered while still hot, and the filter cake was washed with hot water cooled The resulting crystals were suction-filtered off washed with water dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-chloro-2-methylbenzenesulphonamide (103 mg, 0.5 mmol) in CH3CN was added potassium carbonate (100 mg), followed 5-bromomethyl-2-methylbenzothiazole (121 mg, 0.5 mmol). The mixture was refluxed under N2 for 6 h, partitioned between ethyl acetate and water. The organic phase was washed brine, dried over sodium sulphate and concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution). STX1029 was obtained as white solid. TLC single spot at Rf 0.55 (10% EtOAc/DCM); HPLC purity >99% (tR 2.0 min in 10% water-methanol); 1HNMR (270 MHz, CDCl3) δ7.89 (1H, d, J=7.9 Hz, ArH), 7.66 (1H, d, J=7.9 Hz, ArH), 7.65 (1H, d, J=1.3 Hz, ArH), 7.49 (1H, d, J=7.9 Hz, ArH), 7.17 (1H, t, J=7.9 Hz, ArH), 7.13 (1H, dd, J=7.9, 1.5 Hz, ArH), 5.35 (1H, t, J=5.9 Hz, NH), 4.24 (2H, d, J=5.9 Hz, CH2), 2.79 (3H, s, CH3), 2.62 (3H, s, CH3); APCI-MS 367 (MH)+; FAB-HRMS calcd for C16H16ClN2O2S2 (MH+) 367.0342, found 367.0330. The mixture was refluxed under N2 for 6 h partitioned between ethyl acetate and water The organic phase was washed brine dried over sodium sulphate concentrated in vacuo to give a yellow residue, which was separated with flash chromatography (ethyl acetate/DCM, gradient elution)