3-amino-N,N-dimethylbenzenesulfonamide

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

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

Procedure: Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[(dimethylamino)sulfonyl]aniline to generate the title compound. The 3-[(dimethylamino)sulfonyl]aniline was prepared by sequential treatment of commercial 3-nitrobenzenesulfonyl chloride with Me2NH in CH2Cl2 containing (i-Pr)2NEt followed by reduction with SnCl2 in EtOAc at 20° C.

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

Procedure: Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[(dimethylamino)sulfonyl]aniline to generate the title compound. The 3-[(dimethylamino)sulfonyl]aniline was prepared by sequential treatment of commercial 3-nitrobenzenesulfonyl chloride with Me2NH in CH2Cl2 containing (i-Pr)2NEt followed by reduction with SnCl2 in EtOAc at 20° C.

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

Procedure: The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) and 3-amino-N,N-dimethyl-benzenesulfonamide [CAS 6274-18-6; commercially available] according to general procedure II. Light yellow solid. MS (ISP) 540.4 [(M+H)+]; mp 197° C.

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

Procedure: The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) and 3-amino-N,N-dimethyl-benzenesulfonamide [CAS 6274-18-6; commercially available] according to general procedure II. Yellow solid. MS (ISP) 558.3 [(M+H)+]; mp 210° C.

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

Procedure: The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) and 3-amino-N,N-dimethyl-benzenesulfonamide [CAS 6274-18-6; commercially available] according to general procedure II. Yellow solid. MS (ISP) 558.3 [(M+H)+]; mp 210° C.

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

Procedure: To a solution of the above N,N-dimethyl-3-nitro-benzenesulfonamide (20.4 mmol, 4.7 g) in ethanol (50 mL) was added SnCl2 (105 mmol, 19.9 g) and the mixture was refluxed for 1 hour. Upon cooling, the solvent was removed in vacuo. Ethyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue followed by another 200 mL ethyl acetate and 500 mL water. The phases were separated and the organic phase was washed twice with water. The organic phase was filtered, washed with water (2×100 mL) dried over MgSO4 and evaporated to leave the title compound. the mixture was refluxed for 1 hour Upon cooling the solvent was removed in vacuo Ethyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue The phases were separated the organic phase was washed twice with water The organic phase was filtered washed with water (2×100 mL) dried over MgSO4 evaporated

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

Procedure: To a solution of the above N,N-dimethyl-3-nitro-benzenesulfonamide (20.4 mmol, 4.7 g) in ethanol (50 mL) was added SnCl2 (105 mmol, 19.9 g) and the mixture was refluxed for 1 hour. Upon cooling, the solvent was removed in vacuo. Ethyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue followed by another 200 mL ethyl acetate and 500 mL water. The phases were separated and the organic phase was washed twice with water. The organic phase was filtered, washed with water (2×100 mL) dried over MgSO4 and evaporated to leave the title compound. the mixture was refluxed for 1 hour Upon cooling the solvent was removed in vacuo Ethyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue The phases were separated the organic phase was washed twice with water The organic phase was filtered washed with water (2×100 mL) dried over MgSO4 evaporated

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

Procedure: Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[(dimethylamino)sulfonyl]aniline to generate the title compound. The 3-[(dimethylamino)sulfonyl]aniline was prepared by sequential treatment of commercial 3-nitrobenzenesulfonyl chloride with Me2NH in CH2Cl2 containing (i-Pr)2NEt followed by reduction with SnCl2 in EtOAc at 20° C.