N-tert-butyl-1-chloromethanesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-chloro-2-hydroxy-benzaldehyde (13.9 g, 89.2 mmol), K2CO3 (24.6 g, 178.3 mmol) and N-tert-butyl-C-chloro-methanesulfonamide (16.5 g, 89.2 mmol) in DMF (20 mL) was heated at 60° C. overnight. After cooled to room temperature, the mixture was neutralized by addition of aqueous HCl solution and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was washed with diethyl ether to give the title compound (13.5 g). After cooled to room temperature extracted with ethyl acetate The organic phase was washed with water, brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was washed with diethyl ether

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

Procedure: At 0° C., to a mixture of tert-butylamine (10.3 g, 141 mmol) and N-methylmorpholine (14.9 g, 147 mmol) in diethyl ether (200 mL) was added dropwise a solution of chloromethanesulfonyl chloride (20 g, 134 mmol) in diethyl ether (400 mL). After stirred for 5 h, the solution was diluted with ethyl acetate (200 mL). The organic phase was washed with HCl solution (1 N), water and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a colorless oil (16 g). The organic phase was washed with HCl solution (1 N), water and brine dried over anhydrous Na2SO4 concentrated

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

Procedure: At 0° C., to a mixture of tert-butylamine (10.3 g, 141 mmol) and N-methylmorpholine (14.9 g, 147 mmol) in diethyl ether (200 mL) was added dropwise a solution of chloromethanesulfonyl chloride (20 g, 134 mmol) in diethyl ether (400 mL). After stirred for 5 h, the solution was diluted with ethyl acetate (200 mL). The organic phase was washed with HCl solution (1 N), water and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a colorless oil (16 g). The organic phase was washed with HCl solution (1 N), water and brine dried over anhydrous Na2SO4 concentrated

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

Procedure: N-tert-Butyl-1-[(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]methanesulfonamide was prepared from [(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (from Example 1) and N-tert-butyl-1-chloromethanesulfonamide following General Procedure H.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-chloro-2-hydroxy-benzaldehyde (13.9 g, 89.2 mmol), K2CO3 (24.6 g, 178.3 mmol) and N-tert-butyl-C-chloro-methanesulfonamide (16.5 g, 89.2 mmol) in DMF (20 mL) was heated at 60° C. overnight. After cooled to room temperature, the mixture was neutralized by addition of aqueous HCl solution and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was washed with diethyl ether to give the title compound (13.5 g). After cooled to room temperature extracted with ethyl acetate The organic phase was washed with water, brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was washed with diethyl ether

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

Procedure: At 0° C., to a mixture of tert-butylamine (10.3 g, 141 mmol) and N-methylmorpholine (14.9 g, 147 mmol) in diethyl ether (200 mL) was added dropwise a solution of chloromethanesulfonyl chloride (20 g, 134 mmol) in diethyl ether (400 mL). After stirred for 5 h, the solution was diluted with ethyl acetate (200 mL). The organic phase was washed with HCl solution (1 N), water and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a colorless oil (16 g). The organic phase was washed with HCl solution (1 N), water and brine dried over anhydrous Na2SO4 concentrated