1-(2-chlorophenyl)-2-phenylethanone

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2-chlorophenyl)-2-phenylethanone (100 mg, 0.43 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (91 mg, 0.43 mmol), and urea (60 mg, 1.29 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution. The mixture was stirred at 130° C. for 2 days, concentrated under reduced pressure, and purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 51 (28.7 mg, yield 14.2%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.19-7.04 (m, 5H), 6.79 (d, J=6.0 Hz, 3H), 6.72 (s, 2H), 5.23 (s, 1H), 3.88-3.85 (m, 2H), 1.81 (t, J=6.8 Hz, 3H); MS (ESI): m/z 466.2 [M+1]+. concentrated under reduced pressure purified by preparative HPLC (40-70% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)