but-3-en-1-amine

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: 150 mg (0.34 mmol) Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester in 1.5 ml DMF were treated with 140 μl (1.7 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was diluted with ether and water, the organic phase was washed with 0.5 M NaOH, and dried over Na2SO4. Column chromatography on silica gel gave 80 mg (56%) 2-(Methyl-{5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl}-amino)-ethanol as light yellow, MS: 419 (MH+). the organic phase was washed with 0.5 M NaOH dried over Na2SO4

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

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

Procedure: 150 mg (0.34 mmol) Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester in 1.5 ml DMF were treated with 140 μl (1.7 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was diluted with ether and water, the organic phase was washed with 0.5 M NaOH, and dried over Na2SO4. Column chromatography on silica gel gave 80 mg (56%) 2-(Methyl-{5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl}-amino)-ethanol as light yellow, MS: 419(MH+). the organic phase was washed with 0.5 M NaOH dried over Na2SO4

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

Procedure: 150 mg (0.34 mmol) Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester in 1.5 ml DMF were treated with 140 μl (1.7 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was diluted with ether and water, the organic phase was washed with 0.5 M NaOH, and dried over Na2SO4. Column chromatography on silica gel gave 80 mg (56%) 2-(Methyl-{5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl}-amino)-ethanol as light yellow, MS: 419(MH+). the organic phase was washed with 0.5 M NaOH dried over Na2SO4

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

Procedure: But-3-enylamine (1.0 mole), the diethyl acetal of 3-bromopropionaldehyde (1.0 mole) and methanol (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux with stirring for a period of about 6 hours. After this time the reaction mixture is cooled to room temperature and sodium hydroxide (20 grams) is added. The reaction mixture is then stirred for an additional period of about 16 hours. The mixture is then filtered and the filtrate is distilled to yield the desired product the diethyl acetal of 3-but-3-enylaminopropionaldehyde. equipped with a mechanical stirrer thermometer and reflux condenser The reaction mixture is heated at reflux The reaction mixture is then stirred for an additional period of about 16 hours The mixture is then filtered the filtrate is distilled

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

Procedure: But-3-enylamine (1.0 mole), the diethyl acetal of 3-bromopropionaldehyde (1.0 mole) and methanol (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux with stirring for a period of about 6 hours. After this time the reaction mixture is cooled to room temperature and sodium hydroxide (20 grams) is added. The reaction mixture is then stirred for an additional period of about 16 hours. The mixture is then filtered and the filtrate is distilled to yield the desired product the diethyl acetal of 3-but-3-enylaminopropionaldehyde. equipped with a mechanical stirrer thermometer and reflux condenser The reaction mixture is heated at reflux The reaction mixture is then stirred for an additional period of about 16 hours The mixture is then filtered the filtrate is distilled

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

Procedure: 150 mg (0.34 mmol) Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester in 1.5 ml DMF w ere treated with 140 μl (1.7 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was diluted with ether and water, the organic phase was washed with 0.5 M NaOH, and dried over Na2SO4. Column chromatography on silica gel gave 80 mg (56%) 2-(Methyl-{5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl}-amino)-ethanol as light yellow, MS: 419(MH+). the organic phase was washed with 0.5 M NaOH dried over Na2SO4

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

Procedure: 150 mg (0.34 mmol) Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester in 1.5 ml DMF w ere treated with 140 μl (1.7 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was diluted with ether and water, the organic phase was washed with 0.5 M NaOH, and dried over Na2SO4. Column chromatography on silica gel gave 80 mg (56%) 2-(Methyl-{5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl}-amino)-ethanol as light yellow, MS: 419(MH+). the organic phase was washed with 0.5 M NaOH dried over Na2SO4

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

Procedure: 2.15 milliliters (2.32 grams, 20.0 millimoles) of methyl acetoacetate was added with stirring to 1.42 grams (20.0 millimoles) of homoallylamine cooled in an ice bath and the stirring continued while the mixture was allowed to warm to room temperature and thereafter for three hours to obtain a methyl 2-(3-butenyl)aminocrotonate intermediate product and water by-product in the reaction mixture. cooled in an ice bath

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

Procedure: To a suspension of 1-chloro-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile (150 mg) in 15 mL isopropanol was added to 6 mL of a 0.81 M solution of 4-amino-1-butene. The mixture was heated to reflux for 4 days, then cooled to room temp and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic solutions were washed with brine (1×), dried over MgSO4, and concentrated. Flash chromatography (3% to 50% EtOAc in hexanes) provided 146 mg of 1-(but-3-enylamino)-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile as a tan solid. The mixture was heated to reflux for 4 days partitioned between EtOAc and saturated aqueous sodium bicarbonate The organic solutions were washed with brine (1×) dried over MgSO4 concentrated