(E)-hex-2-enoyl chloride

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

Procedure: To 4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride (26.2 mg, 0.1 mmol), dissolved in 0.5 ml anhydrous dichloromethane, polymer-supported diisopropylethylamine (80 mg, 3-4 mmol/g) was added followed by (E)-hex-2-enoyl chloride (19.9 mg, 0.15 mmol) dissolved in anhydrous dichloromethane (1 ml). The mixture was shaken at room temperature for 20 minutes, filtered and the filtrate evaporated to dryness under reduced pressure. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 9 mg of a solid (0.028 mmol, 28%). filtered the filtrate evaporated to dryness under reduced pressure The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

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

Procedure: N-(2-Methoxy-4-quinolyl)ethane-1,2-diamine (21.7 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml) together with triethylamine (17.4 μl, 0.125 mmol). (E)-hex-2-enoyl chloride (16.6 mg, 0.125 mmol) was added and the mixture was shaken for 10 minutes, diluted with dichloromethane and washed with 10% sodium bicarbonate solution (2 times), water and evaporated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%). washed with 10% sodium bicarbonate solution (2 times), water evaporated to dryness under reduced pressure The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%)

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

Procedure: To 4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride (26.2 mg, 0.1 mmol), dissolved in 0.5 ml anhydrous dichloromethane, polymer-supported diisopropylethylamine (80 mg, 3-4 mmol/g) was added followed by (E)-hex-2-enoyl chloride (19.9 mg, 0.15 mmol) dissolved in anhydrous dichloromethane (1 ml). The mixture was shaken at room temperature for 20 minutes, filtered and the filtrate evaporated to dryness under reduced pressure. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 9 mg of a solid (0.028 mmol, 28%). filtered the filtrate evaporated to dryness under reduced pressure The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

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

Procedure: N-(2-Methoxy-4-quinolyl)ethane-1,2-diamine (21.7 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml) together with triethylamine (17.4 μl, 0.125 mmol). (E)-hex-2-enoyl chloride (16.6 mg, 0.125 mmol) was added and the mixture was shaken for 10 minutes, diluted with dichloromethane and washed with 10% sodium bicarbonate solution (2 times), water and evaporated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%). washed with 10% sodium bicarbonate solution (2 times), water evaporated to dryness under reduced pressure The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%)

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

Procedure: N-(2-Methoxy-4-quinolyl)ethane-1,2-diamine (21.7 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml) together with triethylamine (17.4 μl, 0.125 mmol). (E)-hex-2-enoyl chloride (16.6 mg, 0.125 mmol) was added and the mixture was shaken for 10 minutes, diluted with dichloromethane and washed with 10% sodium bicarbonate solution (2 times), water and evaporated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%). washed with 10% sodium bicarbonate solution (2 times), water evaporated to dryness under reduced pressure The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%)

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

Procedure: To 4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-5-yl]quinoline hydrochloride (26.2 mg, 0.1 mmol), dissolved in 0.5 ml anhydrous dichloromethane, polymer-supported diisopropylethylamine (80 mg, 3-4 mmol/g) was added followed by (E)-hex-2-enoyl chloride (19.9 mg, 0.15 mmol) dissolved in anhydrous dichloromethane (1 ml). The mixture was shaken at room temperature for 20 minutes, filtered and the filtrate evaporated to dryness under reduced pressure. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile) to yield 9 mg of a solid (0.028 mmol, 28%). filtered the filtrate evaporated to dryness under reduced pressure The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

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

Procedure: N-(2-Methoxy-4-quinolyl)ethane-1,2-diamine (21.7 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (1 ml) together with triethylamine (17.4 μl, 0.125 mmol). (E)-hex-2-enoyl chloride (16.6 mg, 0.125 mmol) was added and the mixture was shaken for 10 minutes, diluted with dichloromethane and washed with 10% sodium bicarbonate solution (2 times), water and evaporated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%). washed with 10% sodium bicarbonate solution (2 times), water evaporated to dryness under reduced pressure The resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.4 mg (0.0109 mmol, 11%)