butane-2-sulfonamide

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

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

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

Procedure: N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.41 g, 2.1 mmol), 4-dimethylaminopyridine (0.26 g, 2.1 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.9 mL, 4.2 mmol) were added to a solution of 2,4,5-trifluorobenzoic acid (0.25 g, 1.4 mmol) in DCM. After 10 minutes butane-2-sulfonamide (Preparation 29, 0.29 g, 2.1 mmol) was added and the reaction was left at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to yield the title compound as a white solid (0.19 g, 31% yield): The reaction mixture was concentrated in vacuo the residue purified by preparative HPLC

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

Procedure: Prepared according to Preparation 42 using 2,4,5-trifluorobenzoic acid (0.25 g, 1.4 mmol) and butane-2-sulfonamide (0.0.29 g, 2.1 mmol) to yield the title compound (0.19 g, 45%) as a white solid. Prepared

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

Procedure: Prepared according to Preparation 42 using 2,4,5-trifluorobenzoic acid (0.25 g, 1.4 mmol) and butane-2-sulfonamide (0.0.29 g, 2.1 mmol) to yield the title compound (0.19 g, 45%) as a white solid. Prepared

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

Procedure: In a 100 mL round-bottomed flask (RBF) was added carboxylic acid 1 (575 mg, 1.291 mmol) and 1,1′-carbonyldiimidazole (460 mg, 2.84 mmol) in THF (15 mL) to give a yellow solution. The mixture was stirred at room temperature under nitrogen for 1 hour then heated to 70° C., in an oil bath, for 90 minutes. The mixture was cooled and sec-butyl sulfonamide (921 mg, 6.71 mmol) in 4 mL of THF was added along with neat DBU (0.389 mL, 2.58 mmol). The RBF was returned to the oil bath and heated overnight at 70° C. The reaction mixture was transferred to a separatory funnel, diluted with 100 mL of DCM, washed ×3 with 100 mL of 0.5 M HCl, then with 100 mL of H2O, and finally saturated NaCl. The organic mixture was dried over MgSO4, filtered and concentrated to give 713 mgs of the desired acylsulfonamide 2 as a yellow solid (96% yield) which was placed under vacuum overnight. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10μ, C18, 4.6×30 mm column, using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min., a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min., a hold time of 1 min., and an analysis time of 3 min. where solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (500 MHz, CD3OD): δ ppm 0.84-0.92 (m, 3 H), 1.03 (t, J=7.32 Hz, 3 H), 1.23 (m, 1 H), 1.28-1.44 (m, 7 H), 1.58 (m, 1 H), 1.72 (m, 2 H), 1.85 (m, 1 H), 1.95-2.07 (m, 3 H), 2.17 (m, 1 H), 2.78 (m, 1 H), 3.69 (m, 2 H), 3.83-3.91 (m, 3 H), 7.02 (s, 1 H), 7.11 (m, 1 H), 7.47 (d, J=7.63 Hz, 1 H), 7.74 (m, 3 H), 8.25 (s, 1 H). LC/MS: m/z 565.22, Rf 2.192 min., 97.5% purity. to give a yellow solution then heated to 70° C., in an oil bath, for 90 minutes The mixture was cooled heated overnight at 70° C The reaction mixture was transferred to a separatory funnel washed ×3 with 100 mL of 0.5 M HCl The organic mixture was dried over MgSO4 filtered concentrated

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

Procedure: The general method of procedure A was followed using 2-butanesulfonamide (10 g), 1N sodium hydroxide (73 ml) and 3,4-dichlorophenyl isocyanate (13 g). 1N HCl was added and after removal of the acetone the solid was diluted with water, collected, and dried at 65° C. under vacuum. The solid was recrystallized in acetone and hexane to provide 5.2 g of product. after removal of the acetone the solid was diluted with water collected dried at 65° C. under vacuum The solid was recrystallized in acetone

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

Procedure: The general method of procedure A was followed with 2-butanesulfonamide (10 g, 73 mmole), 1N sodium hydroxide (73 ml), and 4-bromophenyl isocyanate (13.7 g). The filtrate from the reaction mixture was treated with 1N HCl and the resulting precipitate redissolved in 1N sodium hydroxide and reprecipitated with 1N HCl. The solid product was collected and dried at 65° C. under vacuum. The dissolution and precipitation procedure was repeated to provide 13.0 g of product which had the following analysis. reprecipitated with 1N HCl The solid product was collected dried at 65° C. under vacuum The dissolution and precipitation procedure

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

Procedure: The method of Example 10 was followed with 2-butanesulfonamide (6.85 g), methanol (250 ml), sodium methoxide (2.7 g), tetrahydrofuran (250 ml) and 4-chlorophenyl isocyanate (7.7 g) with the resulting solid being recrystallized from ethyl acetate to give 2.7 g of white crystals with a melting point of 172-174° C. being recrystallized from ethyl acetate

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

Procedure: The general method of procedure B was followed with 2-butanesulfonamide (6.85 g), sodium methoxide (2.7 g), methanol (250 ml), and 4-fluorophenyl isocyanate (6.8 g) except 1N HCl was added to provide the free urea. The solid was recrystallized from benzene to provide 5.2 g of white powder with a melting point of 136-138° C. was added

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

Procedure: The general method of procedure A was followed using 2-butanesulfonamide (10 g), 1N sodium hydroxide (73 ml) and 3,4-dichlorophenyl isocyanate (13 g). 1N HCl was added and after removal of the acetone the solid was diluted with water, collected, and dried at 65° C. under vacuum. The solid was recrystallized in acetone and hexane to provide 5.2 g of product. after removal of the acetone the solid was diluted with water collected dried at 65° C. under vacuum The solid was recrystallized in acetone

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

Procedure: The general method of procedure A was followed with 2-butanesulfonamide (10 g, 73 mmole), 1N sodium hydroxide (73 ml), and 4-bromophenyl isocyanate (13.7 g). The filtrate from the reaction mixture was treated with 1N HCl and the resulting precipitate redissolved in 1N sodium hydroxide and reprecipitated with 1N HCl. The solid product was collected and dried at 65° C. under vacuum. The dissolution and precipitation procedure was repeated to provide 13.0 g of product which had the following analysis. reprecipitated with 1N HCl The solid product was collected dried at 65° C. under vacuum The dissolution and precipitation procedure