1H-pyrrole-2-carbohydrazide

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(2-pyrrolyl)-5-thiono-5,6-dihydro[1,2,4]triazolo[1,5-c]quinazoline (4.28 g), prepared from 5-chloro-2-isothiocyanatobenzonitrile and 2-pyrrolecarbohydrazide as described in Example 39, is placed in a stainless steel pressure vessel with 40% aqueous methylamine saturated at 0° with methylamine gas (225 ml) and heated 6 hours at an outside temperature of 150° C. The reaction mixture is cooled to room temperature and the solid collected, washed with water and air dried. Recrystallization from aqueous methanol, then water affords pure 5-methylimino-5,6-dihydro-2-(2-pyrrolyl)-[1,2,4]triazolo-[1,5-c]quinazoline, mp 220°-221°. The reaction mixture is cooled to room temperature the solid collected washed with water and air dried Recrystallization from aqueous methanol

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(2-pyrrolyl)-5-thiono-5,6-dihydro[1,2,4]triazolo[1,5-c]quinazoline (4.28 g), prepared from 5-chloro-2-isothiocyanatobenzonitrile and 2-pyrrolecarbohydrazide as described in Example 39, is placed in a stainless steel pressure vessel with 40% aqueous methylamine saturated at 0° with methylamine gas (225 ml) and heated 6 hours at an outside temperature of 150° C. The reaction mixture is cooled to room temperature and the solid collected, washed with water and air dried. Recrystallization from aqueous methanol, then water affords pure 5-methylimino-5,6-dihydro-2-(2-pyrrolyl)-[1,2,4]triazolo-[1,5-c]quinazoline, mp 220°-221°. The reaction mixture is cooled to room temperature the solid collected washed with water and air dried Recrystallization from aqueous methanol

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrazine monohydrate (31.0, 620 mmol) was added to a mixture of methyl 1H-pyrrole-2-carboxylate and methanol (100 ml) followed by stirring at 65° C. for 15 h. The mixture was evaporated and the product was isolated as a crystalline solid. The mixture was evaporated the product was isolated as a crystalline solid

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrazine monohydrate (31.0, 620 mmol) was added to a mixture of methyl 1H-pyrrole-2-carboxylate and methanol (100 ml) followed by stirring at 65° C. for 15 h. The mixture was evaporated and the product was isolated as a crystalline solid. The mixture was evaporated the product was isolated as a crystalline solid

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

Procedure: Potassium hydroxide (4.78 g, 85.3 mmol) was solved in methanol (125 ml). 1H-pyrrole-2-carbohydrazide (Compound C) (9.7 g, 77.5 mmol) was added and the mixture was stirred for 30 minutes. Carbon disulfide (14.7 g, 193.8 mmol) was added to the mixture followed by stirring at 65° C. for 15 h. Another equivalent of carbon disulfide (5.90 g, 77.5 mmol) was added followed by stirring at 65° C. for 4 days. Aqueous hydrochloric acid (1 M) was added in excess quantity, the mixture was stirred and filtered and washed with aqueous hydrochloric acid. Yield 10 g (77%). by stirring at 65° C. for 15 h by stirring at 65° C. for 4 days the mixture was stirred filtered washed with aqueous hydrochloric acid

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

Procedure: To 0.750 g of 1H-pyrrole-2-carbohydrazide (5.99 mmol) in 50 ml tetrahydrofuran was added 1.315 g 4-bromobenzoyl chloride (5.99 mmol) and 1 ml pyridine (11.99 mmol) at room temperature under nitrogen. After one hour of stirring at room temperature, the desired product precipitated. The precipitate was filtered, washed with minimum dichloromethane and methanol and dried to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 10.47 (s, 1H), 10.04 (s, 1H), 7.84-7.88 (m, 2H), 7.75 (d, J=8.8, 1H), 7.75 (q, J=4.2, 1H), 6.91-6.95 (m, 2H), 6.33-6.15 (m, 1H). the desired product precipitated The precipitate was filtered washed with minimum dichloromethane and methanol dried

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(2-pyrrolyl)-5-thiono-5,6-dihydro[1,2,4]triazolo[1,5-c]quinazoline (4.28 g), prepared from 5-chloro-2-isothiocyanatobenzonitrile and 2-pyrrolecarbohydrazide as described in Example 39, is placed in a stainless steel pressure vessel with 40% aqueous methylamine saturated at 0° with methylamine gas (225 ml) and heated 6 hours at an outside temperature of 150° C. The reaction mixture is cooled to room temperature and the solid collected, washed with water and air dried. Recrystallization from aqueous methanol, then water affords pure 5-methylimino-5,6-dihydro-2-(2-pyrrolyl)-[1,2,4]triazolo-[1,5-c]quinazoline, mp 220°-221°. The reaction mixture is cooled to room temperature the solid collected washed with water and air dried Recrystallization from aqueous methanol

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrazine monohydrate (31.0, 620 mmol) was added to a mixture of methyl 1H-pyrrole-2-carboxylate and methanol (100 ml) followed by stirring at 65° C. for 15 h. The mixture was evaporated and the product was isolated as a crystalline solid. The mixture was evaporated the product was isolated as a crystalline solid

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

Procedure: Potassium hydroxide (4.78 g, 85.3 mmol) was solved in methanol (125 ml). 1H-pyrrole-2-carbohydrazide (Compound C) (9.7 g, 77.5 mmol) was added and the mixture was stirred for 30 minutes. Carbon disulfide (14.7 g, 193.8 mmol) was added to the mixture followed by stirring at 65° C. for 15 h. Another equivalent of carbon disulfide (5.90 g, 77.5 mmol) was added followed by stirring at 65° C. for 4 days. Aqueous hydrochloric acid (1 M) was added in excess quantity, the mixture was stirred and filtered and washed with aqueous hydrochloric acid. Yield 10 g (77%). by stirring at 65° C. for 15 h by stirring at 65° C. for 4 days the mixture was stirred filtered washed with aqueous hydrochloric acid

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrazine monohydrate (31.0 g, 620 mmol) was added to a mixture of methyl 1H-pyrrole-2-carboxylate (10 g, 77.5 mmol) and methanol (100 ml) followed by stirring at 65° C. for 15 h. The mixture was evaporated and the product was isolated as a crystalline solid. The mixture was evaporated the product was isolated as a crystalline solid

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

Procedure: Potassium hydroxide (4.78 g, 85.3 mmol) was solved in methanol (125 ml). 1H-pyrrole-2-carbohydrazide (9.7 g, 77.5 mmol) was added and the mixture was stirred for 30 minutes. Carbon disulfide (14.7 g, 193.8 mmol) was added to the mixture followed by stirring at 65° C. for 15 h. Another equivalent of carbon disulfide (5.90 g, 77.5 mmol) was added followed by stirring at 65° C. for 4 days. Aqueous hydrochloric acid (1 M) was added in excess quantity, the mixture was stirred and filtered and washed with aqueous hydrochloric acid. Yield 10 g (77%). by stirring at 65° C. for 15 h by stirring at 65° C. for 4 days the mixture was stirred filtered washed with aqueous hydrochloric acid

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

Procedure: To 0.750 g of 1H-pyrrole-2-carbohydrazide (5.99 mmol) in 50 ml tetrahydrofuran was added 1.315 g 4-bromobenzoyl chloride (5.99 mmol) and 1 ml pyridine (11.99 mmol) at room temperature under nitrogen. After one hour of stirring at room temperature, the desired product precipitated. The precipitate was filtered, washed with minimum dichloromethane and methanol and dried to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 10.47 (s, 1H), 10.04 (s, 1H), 7.84-7.88 (m, 2H), 7.75 (d, J=8.8, 1H), 7.75 (q, J=4.2, 1H), 6.91-6.95 (m, 2H), 6.33-6.15 (m, 1H). the desired product precipitated The precipitate was filtered washed with minimum dichloromethane and methanol dried