4-cyano-N-methylbutane-1-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: 4-Chloro-N-methylbutane-1-sulfonamide (54 mmol), KCN (108 mmol) and 18-crown ether-6 (11 mmol) were dissolved in CH3CN (100 ml). The mixture was stirred at reflux temperature overnight. The mixture was cooled and filtered. The residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2, then ethyl acetate). Yield: 3.2 g (70% purity). at reflux temperature overnight The mixture was cooled filtered The residue was purified by flash column chromatography over silica gel (eluent

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

Procedure: A mixture of 4-cyano-N-methylbutane-1-sulfonamide (Example 9; 100 mmol), acetic acid (100 ml) and concentrated hydrochloric acid (100 ml) was refluxed for 5 hours and then concentrated in vacuo. The residue was taken on THF and then filtered off. The filtrate was concentrated and the residue was washed with dichloromethane to give the pure product (11 g; 58% yield). was refluxed for 5 hours concentrated in vacuo filtered off The filtrate was concentrated the residue was washed with dichloromethane to give the pure product (11 g; 58% yield)

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

Procedure: A mixture of 4-cyano-N-methylbutane-1-sulfonamide (Example 9; 91.2 mmol) and Pd/C (10 mol %, 1 g) in methanol/7N NH3 (180 ml) was put under a hydrogen atmosphere. The mixture was stirred overnight at room temperature. The mixture was filtered and concentrated. The crude product was used in the next step without further purification. The mixture was filtered concentrated The crude product was used in the next step without further purification

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

Procedure: A mixture of 4-cyano-N-methylbutane-1-sulfonamide (Example 9; 91.2 mmol) and Pd/C (10 mol %, 1 g) in methanol/7N NH3 (180 ml) was put under a hydrogen atmosphere. The mixture was stirred overnight at room temperature. The mixture was filtered and concentrated. The crude product was used in the next step without further purification. The mixture was filtered concentrated The crude product was used in the next step without further purification

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

Procedure: A solution of 4-chloro-N-methylbutane-1-sulfonamide (Example 5; 86.7 mmol), and sodium iodide (95.4 mmol) in DMF (175 ml) was stirred for 10 min at room temperature. Sodium cyanide (191 mmol) was added and the mixture was stirred overnight at 60° C. The mixture was filtered off and the filtrate was extracted with AcOEt/water. The crude product was concentrated and was used without further purification in the next step (Examples 10 and 20). The mixture was filtered off the filtrate was extracted with AcOEt/water The crude product was concentrated was used without further purification in the next step (Examples 10 and 20)

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

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

Procedure: 4-Chloro-N-methylbutane-1-sulfonamide (54 mmol), KCN (108 mmol) and 18-crown ether-6 (11 mmol) were dissolved in CH3CN (100 ml). The mixture was stirred at reflux temperature overnight. The mixture was cooled and filtered. The residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2, then ethyl acetate). Yield: 3.2 g (70% purity). at reflux temperature overnight The mixture was cooled filtered The residue was purified by flash column chromatography over silica gel (eluent

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

Procedure: A mixture of 4-cyano-N-methylbutane-1-sulfonamide (Example 9; 100 mmol), acetic acid (100 ml) and concentrated hydrochloric acid (100 ml) was refluxed for 5 hours and then concentrated in vacuo. The residue was taken on THF and then filtered off. The filtrate was concentrated and the residue was washed with dichloromethane to give the pure product (11 g; 58% yield). was refluxed for 5 hours concentrated in vacuo filtered off The filtrate was concentrated the residue was washed with dichloromethane to give the pure product (11 g; 58% yield)

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

Procedure: A mixture of 4-cyano-N-methylbutane-1-sulfonamide (Example 9; 91.2 mmol) and Pd/C (10 mol %, 1 g) in methanol/7N NH3 (180 ml) was put under a hydrogen atmosphere. The mixture was stirred overnight at room temperature. The mixture was filtered and concentrated. The crude product was used in the next step without further purification. The mixture was filtered concentrated The crude product was used in the next step without further purification

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

Procedure: A solution of 4-chloro-N-methylbutane-1-sulfonamide (Example 5; 86.7 mmol), and sodium iodide (95.4 mmol) in DMF (175 ml) was stirred for 10 min at room temperature. Sodium cyanide (191 mmol) was added and the mixture was stirred overnight at 60° C. The mixture was filtered off and the filtrate was extracted with AcOEt/water. The crude product was concentrated and was used without further purification in the next step (Examples 10 and 20). The mixture was filtered off the filtrate was extracted with AcOEt/water The crude product was concentrated was used without further purification in the next step (Examples 10 and 20)