1-(4-aminophenyl)butan-1-one

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 20 ml vial, to a solution of solution of 1-(4-aminophenyl)butan-1-one (46 mg, 0.28 mmol) dissolved in DCM/MeOH (0.6 mL) was added a solution of 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (112 mg, 0.56 mmol) in DMA (1.8 mL). A solution of acetic acid (50 mg, 0.84 mmol) in DCM/MeOH (0.6 mL) was then added, followed by the addition of 361 mg of MP-CNBH3 resin (3 eq.; subst. 2.34 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The resulting residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound. The vial was capped was then heated After completion of the reaction the reaction mixture was concentrated to dryness The resulting residue was dissolved in 1:1 DMSO/MeOH Purification by reverse phase HPLC (TFA method)

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 20 ml vial, to a solution of solution of 1-(4-aminophenyl)butan-1-one (46 mg, 0.28 mmol) dissolved in DCM/MeOH (0.6 mL) was added a solution of 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (112 mg, 0.56 mmol) in DMA (1.8 mL). A solution of acetic acid (50 mg, 0.84 mmol) in DCM/MeOH (0.6 mL) was then added, followed by the addition of 361 mg of MP-CNBH3 resin (3 eq.; subst. 2.34 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The resulting residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound. The vial was capped was then heated After completion of the reaction the reaction mixture was concentrated to dryness The resulting residue was dissolved in 1:1 DMSO/MeOH Purification by reverse phase HPLC (TFA method)

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 20 mL vial, to a solution of 1-(4-aminophenyl)-butan-1-one (19.64 mg, 0.1 mmol) in DCM/MeOH (0.7 mL) was added a solution of thiophene-3-carbaldehyde (22.4 mg, 0.2 mmol) in DMA (0.8 mL). A solution of acetic acid (18 mg, 0.3 mmol) in DCM/MeOH (0.7 mL) was added, followed by the addition of 160 mg of MP-CNBH3 resin (3 eq.; subst. 2.25 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound. The vial was capped was then heated After completion of the reaction the reaction mixture was concentrated to dryness The residue was dissolved in 1:1 DMSO/MeOH Purification by reverse phase HPLC (TFA method)

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

Procedure: 8.15 g of p-aminobutyrophenone are dissolved in 300 ml of methylene chloride and the solution is cooled to -30° under nitrogen. 5.96 g of tert-butyl hypochlorite are then added dropwise and, in the course of this, the mixture is slowly cooled to -65°. Stirring is then carried out for 10 minutes at -65°, 7.37 g of methylthioacetic acid ethyl ester are added dropwise, the mixture is left for one hour at -65°, 5.55 g of triethylamine are added, and the mixture is slowly allowed to warm to room temperature. 100 ml of water are then added, the organic layer is separated off and subsequently washed with 100 ml of water, the aqueous phases are extracted twice with methylene chloride, and the organic phases are combined, dried over magnesium sulphate, filtered and concentrated to dryness by evaporation under reduced pressure. The residue obtained by concentration by evaporation is dissolved in 200 ml of diethyl ether, 25 ml of 2N hydrochloric acid are added and the mixture is stirred overnight at room temperature. The mixture is then diluted with 50 ml of water, the organic phase is separated off, the aqueous phase is washed with 100 ml of diethyl ether, the organic phases are combined, washed with a mixture of 50 ml of water and 10 ml of 2N hydrochloric acid, dried over magnesium sulphate and concentrated to dryness by evaporation, and the residue is suspended in diethyl ether, filtered with suction and dried under reduced pressure. 5-Butyryl-3-methylthiooxindole having a melting point of 133°-136° is obtained. the solution is cooled to -30° under nitrogen is slowly cooled to -65° the mixture is left for one hour at -65° the organic layer is separated off subsequently washed with 100 ml of water the aqueous phases are extracted twice with methylene chloride dried over magnesium sulphate filtered concentrated to dryness by evaporation under reduced pressure The residue obtained by concentration by evaporation the mixture is stirred overnight at room temperature the organic phase is separated off the aqueous phase is washed with 100 ml of diethyl ether washed with a mixture of 50 ml of water and 10 ml of 2N hydrochloric acid dried over magnesium sulphate concentrated to dryness by evaporation filtered with suction dried under reduced pressure

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

Procedure: 20 g of p-acetaminobutyrophenone are suspended in 40 ml of semi-concentrated hydrochloric acid and the suspension is heated under reflux for 25 minutes and poured into a mixture of 100 ml of ice and 30 ml of concentrated sodium hydroxide solution. The mixture is filtered with suction, then the residue is washed twice with ice-cold water, dried in the atmosphere and recrystallised from methanol/water (20 ml+100 ml). p-Aminobutyrophenone having a melting point of 93°-94° is obtained. the suspension is heated under reflux for 25 minutes The mixture is filtered with suction the residue is washed twice with ice-cold water dried in the atmosphere recrystallised from methanol/water (20 ml+100 ml)

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 20 ml vial, to a solution of solution of 1-(4-aminophenyl)butan-1-one (46 mg, 0.28 mmol) dissolved in DCM/MeOH (0.6 mL) was added a solution of 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (112 mg, 0.56 mmol) in DMA (1.8 mL). A solution of acetic acid (50 mg, 0.84 mmol) in DCM/MeOH (0.6 mL) was then added, followed by the addition of 361 mg of MP-CNBH3 resin (3 eq.; subst. 2.34 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The resulting residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound. The vial was capped was then heated After completion of the reaction the reaction mixture was concentrated to dryness The resulting residue was dissolved in 1:1 DMSO/MeOH Purification by reverse phase HPLC (TFA method)

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 20 mL vial, to a solution of 1-(4-aminophenyl)-butan-1-one (19.64 mg, 0.1 mmol) in DCM/MeOH (0.7 mL) was added a solution of thiophene-3-carbaldehyde (22.4 mg, 0.2 mmol) in DMA (0.8 mL). A solution of acetic acid (18 mg, 0.3 mmol) in DCM/MeOH (0.7 mL) was added, followed by the addition of 160 mg of MP-CNBH3 resin (3 eq.; subst. 2.25 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound. The vial was capped was then heated After completion of the reaction the reaction mixture was concentrated to dryness The residue was dissolved in 1:1 DMSO/MeOH Purification by reverse phase HPLC (TFA method)