1,2-DIBENZOYLETHANE

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide)dihydrochloride, mp 285°-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2′-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2′-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide)dihydrochloride, mp 285°-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide)dihydrochloride, mp 285°-6° C. Cooling concentration and filtration

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

Procedure: 6-(Aminomethyl)pyridin-2-amine (0.050 g, 0.4 mmol) was dissolved in EtOH (2 mL) and Toluene (10 mL) was added. To this mixture was added pTSA (5 mg) and 1,4-diphenyl-1,4-butanedione (0.124 g, 0.4 mmol). The solution was heated to reflux overnight. The solvent was removed and the residue was purified by flash chromatography (20:1 CHCl3: MeOH) to yield 6-[(2,5-diphenyl-1H-pyrrol-1-yl)methyl]pyridin-2-amine as a white solid. mp 143-144° C.; 1H NMR (500 MHz, DMSO-d6) δ: 5.06 (s, 2H), 5.50 (d, 1H, J=7.3 Hz), 5.82 (s, 2H), 6.16 (d, 1H, J=8.1 Hz), 6.34 (s, 2H), 7.18 (t, 1H, J=7.47 Hz), 7.28 (t, 2H, J=8.5 Hz), 7.36 (m, 4H), 7.40 (m, 4H); MS (ES) m/z 326.3. The solution was heated to reflux overnight The solvent was removed the residue was purified by flash chromatography (20:1 CHCl3: MeOH)

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

Procedure: 6-(Aminomethyl)pyridin-2-amine (0.050 g, 0.4 mmol) was dissolved in EtOH (2 mL) and Toluene (10 mL) was added. To this mixture was added pTSA (5 mg) and 1,4-diphenyl-1,4-butanedione (0.124 g, 0.4 mmol). The solution was heated to reflux overnight. The solvent was removed and the residue was purified by flash chromatography (20:1 CHCl3: MeOH) to yield 6-[(2,5-diphenyl-1H-pyrrol-1-yl)methyl]pyridin-2-amine as a white solid. mp 143-144° C.; 1H NMR (500 MHz, DMSO-d6) δ: 5.06 (s, 2H), 5.50 (d, 1H, J=7.3 Hz), 5.82 (s, 2H), 6.16 (d, 1H, J=8.1 Hz), 6.34 (s, 2H), 7.18 (t, 1H, J=7.47 Hz), 7.28 (t, 2H, J=8.5 Hz), 7.36 (m, 4H), 7.40 (m, 4H); MS (ES) m/z 326.3. The solution was heated to reflux overnight The solvent was removed the residue was purified by flash chromatography (20:1 CHCl3: MeOH)

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285°-6° C. Cooling concentration and filtration

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

Procedure: 1,2-dibenzoylethane (4.76 g), aminoguanidine bicarbonate (5.45 g), and concentrated hydrochloric acid (3.33 mL) were heated in 50% ethanol (60 mL) for 24 hr. Cooling, concentration and filtration gave 4.3 g of 2,2'-(1,4-diphenyl-1,4-butanediylidene)bis(hydrazinecarboximidamide) dihydrochloride, mp 285°-6° C. Cooling concentration and filtration