1-amino-3-phenylurea

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

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

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

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

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

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

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.37 g of 1-(2-diisopropylaminoethyl)isatin and 0.86 g of 4-phenylsemicarbazide in ml of a mixture of ethanol and water (2:1) was added 3 drops of acetic acid, and the mixture was stirred for 3 hours at 70° C. The yellow precipitates were collected by filtration, and recrystallized from ethanol to obtain 1.24 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-(4-phenylsemicarbazone) having a melting point of 157°-159° C. The yellow precipitates were collected by filtration recrystallized from ethanol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.37 g of 1-(2-diisopropylaminoethyl)isatin and 0.86 g of 4-phenylsemicarbazide in ml of a mixture of ethanol and water (2:1) was added 3 drops of acetic acid, and the mixture was stirred for 3 hours at 70° C. The yellow precipitates were collected by filtration, and recrystallized from ethanol to obtain 1.24 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-(4-phenylsemicarbazone) having a melting point of 157°-159° C. The yellow precipitates were collected by filtration recrystallized from ethanol

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

Procedure: 4-Phenyl semicarbazide (4.91 g, 33 mmol) was added to a suspension of 3-hydroxy-2-pyridine carbaldehyde (4.0 g, 33 mmol) in a mixture of ethanol water (30 mL:40 mL). The reaction mixture was stirred at room temperature for 3 h and the yellow product was collected by filtration. The yellow precipitate was washed with EtOH/H2O 1:1 and dried under P2 O5 to yield 8.22 g (99%) of product. It can be recrystallized from EtOH/H2O; m.p. 201°-2° C. (dec.). 1H NMR (d6 -DMSO) d: 10.85 (br.s., 1H); 10.6 (br.s., 1H); 9.14 (s, 1H); 8.27 (s, 1H); 8.15 (d of d, 1H); 7.55 (d, 2H); 7.26-7.36 (m, 4H); 7.01 (t, 1H). the yellow product was collected by filtration The yellow precipitate was washed with EtOH/H2O 1:1 dried under P2 O5

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carboxylic acid (204.5 mg, 0.732 mmol), 4-phenylsemicarbazide (111 mg, 0.732 mmol), EDC (140 mg, 0.732 mmol), and HOBT (112 mg, 0.732 mmol) in DMF (3.5 mL) was stirred at 25° C. for 3 h. DIPEA (0.255 mL, 1.464 mmol) was added and the resulting mixture was stirred at 25° C. for 2 h. Additional 4-phenylsemicarbazide (111 mg, 0.732 mmol), HOBT (112 mg, 0.732 mmol), and EDC (140 mg, 0.732 mmol) were sequentially added, and the resulting mixture was stirred at 25° C. for 17 h. The mixture was diluted with H2O (40 mL), and the precipitated solid was collected by vacuum filtration, sequentially washed with H2O (2×30 mL) and Et2O (2×15 mL), and dried in vacuo to provide 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carbonyl)-N-phenylhydrazinecarboxamide (262 mg, 0.635 mmol, 87%) as a tan solid: MS (ESI, pos. ion) m/z: 413.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90-11.97 (1H, m), 10.19-10.25 (1H, m), 8.97-9.00 (1H, m), 8.94-8.97 (1H, m), 8.84 (1H, s), 8.36 (1H, s), 8.32 (1H, d, J=2.7 Hz), 8.15 (1H, s), 7.79 (1H, d, J=8.4 Hz), 7.51-7.55 (1H, m), 7.50 (2H, d, J=8.0 Hz), 7.27 (2H, t, J=7.7 Hz), 6.96 (1H, t, J=7.3 Hz), 2.18-2.27 (1H, m), 1.16-1.22 (2H, m), 1.04-1.13 (2H, m). the resulting mixture was stirred at 25° C. for 2 h the resulting mixture was stirred at 25° C. for 17 h the precipitated solid was collected by vacuum filtration sequentially washed with H2O (2×30 mL) and Et2O (2×15 mL) dried in vacuo

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

Procedure: To a solution of 3,6,7-trichloro-2-(methylsulfonyl)quinoxaline (312 mg, 1.0 mmol) in DMF (10 ml) was added caesium carbonate (489 mg, 1.5 mmol) followed by 4-phenylsemicarbazide (182 mg, 1.2 mmol). The reaction was stirred overnight at room temperature. The product was purified by flash column chromatography using ethyl acetate:hexane 1:1 obtaining the title compound as a solid. The product was purified by flash column chromatography