2-methylpropanimidamide;hydrochloride

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of isobutyramidine hydrochloride (6.47 g, 47.5 mmol) at rt in EtOH (30 ml) under an argon atmosphere was added NaOEt solution (21 ml, 21% in EtOH) over min. The suspension was heated to 50° C. and a solution of mucobromic acid (5.7 g, 22.1 mmol) in EtOH (24 ml) was added dropwise over 5 min at 50° C. An additional portion of NaOEt solution (12 ml, 21% in EtOH) was added dropwise over 5 min. The mixture was then cooled to rt. The solids were filtered off, and the cake was washed with plenty of ethanol. The filtrate was concentrated to leave the crude product as a light brown solid. The crude material was triturated in 2 N HCl (100 ml). The product was collected by filtration, washed with plenty of H2O and plenty of n-heptane and dried to give the product (2.09 g, 73%) as beige solid. The mixture was then cooled to rt The solids were filtered off the cake was washed with plenty of ethanol The filtrate was concentrated to leave the crude product as a light brown solid The crude material was triturated in 2 N HCl (100 ml) The product was collected by filtration washed with plenty of H2O and plenty of n-heptane dried

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

Procedure: A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C. extracted with methylene chloride The methylene chloride solution was dried over anhydrous sodium sulfate concentrated at reduced pressure to give a yellow oil Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

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

Procedure: A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C. extracted with methylene chloride The methylene chloride solution was dried over anhydrous sodium sulfate concentrated at reduced pressure to give a yellow oil Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

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

Procedure: A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C. extracted with methylene chloride The methylene chloride solution was dried over anhydrous sodium sulfate concentrated at reduced pressure to give a yellow oil Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

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

Procedure: A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C. extracted with methylene chloride The methylene chloride solution was dried over anhydrous sodium sulfate concentrated at reduced pressure to give a yellow oil Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

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

Procedure: The title compound was prepared according to the experimental described for compound 230 from 2-(6-chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)acetohydrazide and isobutyrimidamide hydrochloride. M/e+ 352 for C19H19ClN5 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.72 (d, J=8.4 Hz, 2H), 7.29 (m, 5H), 7.00 (dd, J=9.5, 1.8 Hz, 1H), 4.40 (s, 2H), 3.03 (m, 1H), 1.29 (s, 3H), 1.28 (s, 3H) ppm.

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

Procedure: The title compound was prepared according to the experimental described for compound 230 from 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetohydrazide and isobutyrimidamide hydrochloride. M/e+ 352 for C19H19ClN5 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.05 (m, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.27 (m, 4H), 7.04 (t, J=7.3 Hz, 1H), 6.75 (t, J=6.6 Hz, 1H), 4.42 (s, 2H), 3.12 (m, 1H), 1.39 (s, 3H), 1.37 (s, 3H) ppm.

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

Procedure: The title compound was prepared according to the experimental described for compound 230 from 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetohydrazide and isobutyrimidamide hydrochloride. M/e+ 352 for C19H19ClN5 (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.05 (m, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.27 (m, 4H), 7.04 (t, J=7.3 Hz, 1H), 6.75 (t, J=6.6 Hz, 1H), 4.42 (s, 2H), 3.12 (m, 1H), 1.39 (s, 3H), 1.37 (s, 3H) ppm.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of isobutyramidine hydrochloride (6.47 g, 47.5 mmol) at rt in EtOH (30 ml) under an argon atmosphere was added NaOEt solution (21 ml, 21% in EtOH) over min. The suspension was heated to 50° C. and a solution of mucobromic acid (5.7 g, 22.1 mmol) in EtOH (24 ml) was added dropwise over 5 min at 50° C. An additional portion of NaOEt solution (12 ml, 21% in EtOH) was added dropwise over 5 min. The mixture was then cooled to rt. The solids were filtered off, and the cake was washed with plenty of ethanol. The filtrate was concentrated to leave the crude product as a light brown solid. The crude material was triturated in 2 N HCl (100 ml). The product was collected by filtration, washed with plenty of H2O and plenty of n-heptane and dried to give the product (2.09 g, 73%) as beige solid. The mixture was then cooled to rt The solids were filtered off the cake was washed with plenty of ethanol The filtrate was concentrated to leave the crude product as a light brown solid The crude material was triturated in 2 N HCl (100 ml) The product was collected by filtration washed with plenty of H2O and plenty of n-heptane dried

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

Procedure: A mixture of 3.5 g (10 mmole) of 1-(2-chlorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 4.8 g (40 mmole) of isobutyramidine hydrochloride, 10 ml (41 mmole) of a 4.12M methanol solution of sodium methoxide and 100 ml of methanol was stirred at room temperature for 2 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C. Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C. extracted with methylene chloride The methylene chloride solution was dried over anhydrous sodium sulfate concentrated at reduced pressure to give a yellow oil Crystallization of the oil with ether gave a light yellow solid, mp 127°-129° C Recrystallization from a mixture of ether and petroleum ether gave colorless rods, mp 127°-129° C.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of isobutyramidine hydrochloride (6.47 g, 47.5 mmol) at rt in EtOH (30 ml) under an argon atmosphere was added NaOEt solution (21 ml, 21% in EtOH) over min. The suspension was heated to 50° C. and a solution of mucobromic acid (5.7 g, 22.1 mmol) in EtOH (24 ml) was added dropwise over 5 min at 50° C. An additional portion of NaOEt solution (12 ml, 21% in EtOH) was added dropwise over 5 min. The mixture was then cooled to rt. The solids were filtered off, and the cake was washed with plenty of ethanol. The filtrate was concentrated to leave the crude product as a light brown solid. The crude material was triturated in 2 N HCl (100 ml). The product was collected by filtration, washed with plenty of H2O and plenty of n-heptane and dried to give the product (2.09 g, 73%) as beige solid. The mixture was then cooled to rt The solids were filtered off the cake was washed with plenty of ethanol The filtrate was concentrated to leave the crude product as a light brown solid The crude material was triturated in 2 N HCl (100 ml) The product was collected by filtration washed with plenty of H2O and plenty of n-heptane dried

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

Procedure: To a solution of 2-methylpropanimidamide hydrochloride (2.00 g, 16.3 mmol) and perchloromethyl mercaptan (1.75 ml, 16.3 mmol) in dichloromethane (40 ml) was added dropwise a solution of sodium hydroxide (3.26 g, 81.5 mmol) in water (6 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.22 g (46.2%) of the desired product as an oil. cooling The organic layer was separated washed with water dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)