Category: 446273-59-2

446273-59-2, 3-Amino-4-bromo-6-chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,446273-59-2

6-Chloro-4-methylpyridazin-3-amineA 100 mL flask was charged with 4-bromo-6-chloropyridazin-3-amine (1 g, 4.80 mmol), dimethylzinc (9.59 mL, 9.59 mmol), Pd(PPh3)4 (0.277 g, 0.240 mmol) and DMF (10 mL). The reaction mixture was stirred at RT. Then the reaction mixture was quenched with MeOH and concentrated. The crude product was loaded onto a 10 g SCX SPE, and 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH were added. The fractions were combined and concentrated to afford 6-chloro-4-methylpyridazin-3-amine (693 mg, 80% yield).

446273-59-2 3-Amino-4-bromo-6-chloropyridazine 22024419, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

446273-59-2, 3-Amino-4-bromo-6-chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-bromo-6-chloro-pyridazin-3-amine (30.02 g, 143 mmol) and THF (180 mL) were charged into a reaction vessel. Methylmagnesium chloride (22% in THF, 50.0 mL, 1.03 eq.) was added at 20C over 60 minutes, followed by zinc chloride in Me-THF (25%, 37 mL, 0.50 eq.) and palladium tetrakis(triphenyphosphine) (1.66 g, lmol%). The reaction mixture was heated to 50C and methylmagnesium chloride (22% in THF, 81 mL, 1.7 eq.) was added slowly. The reaction mixture was stirred at 50C until complete conversion, then at 10C for 14.5 hours and poured into a mixture of water (90 g), aqueous HCl 33% (52.5 g) and toluene (150 mL) maintained at 20-30C. The aqueous phase was separated and the organic phase was extracted with a solution of aqueous HCl 33% (2.0 g) and water (45 g). The aqueous layers were combined and washed with toluene (30 mL) twice and the pH was adjusted by addition of 25% aqueous ammonia solution. When a pH of 2.4 was reached, seeding crystals were added, the mixture was stirred further for 15 minutes and thereafter the pH was brought to 4.0. The suspension was stirred at 20C for 2 hours, the precipitate was filtered off, washed with water (20 mL) three times to afford crude 6- chloro-4-methyl-pyridazin-3-amine (29 g) as a brown solid. (0302) 29 g crude product was transferred to a reaction vessel and methanol (20 mL) was added. The mixture was refluxed for 30 minutes and 12 g water was added. The solution was cooled to 0C and stirred for 2 hours at this temperature. The precipitate was filtered off, washed with water three times and dried under reduced pressure at 40C to afford purified 6-chloro-4-methyl-pyridazin-3-amine (13.8 g, 66%) as a light brown solid. (0303) Alternative purification: (0304) 50 g crude 6-chloro-4-methyl-pyridazin-3-amine were dissolved in methanol (250 mL) and active charcoal (4.0 g) and diatomaceous earth (2.5 g) were added. The suspension was stirred at 45C for 1 hour, cooled to 30C and potassium hydrogenophosphate (2.1 g) was added. The suspension was stirred at 30C for another 90 minutes, filtered and the precipitate washed with methanol (100 mL). The filtrate was concentrated to a residual volume of 175 mL and water (120 mL) was added. The resulting suspension was heated to reflux affording a solution which was cooled to 20C resulting in a suspension. The precipitate was filtered off, washed with water (90 mL) and dried under reduced pressure to afford pure 6-chloro-4-methyl-pyridazin-3-amine (38 g, 76%) as a light yellow solid.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ADAM, Jean-Michel; FANTASIA, Serena Maria; FISHLOCK, Daniel Vincent; HOFFMANN-EMERY, Fabienne; MOINE, Gerard; PFLEGER, Christophe; MOESSNER, Christian; (73 pag.)WO2019/57740; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-Bromo-6-chloro-pyridazin-3-amine (5.2 g, 25 mmol) was combined with tetrakis(triphenylphosphine)palladium(0) (700 mg, 0.61 mmol) and DMF (50 mL). To the mixture was added dimethylzinc in heptane (50 mL, 50 mmol, 1.0 M) at room temperature. The mixture was heated at 50 C for 2 h then 70 C for 1 h. The mixture was cooled to 0 C and excess reagent was quenched by the addition of H20. The mixture was filtered over Celite and concentrated. The residue was chromatographed on silica gel, eluting with 0-10% MeOH in CH2C12. MS m/z 144.2, 146.2 [M+H]+.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-bromo-6-chloro-pyridazin-3-amine (3.0 g, 14.4 mmol) and (0298) tetrakis(triphenylphosphine)palladium (1666 mg, 144 muiotaetaomicron) were suspended in THF (13.2 g) and a solution of zinc chloride in Me-THF (2.0 M, 9 mL, 18 mmol) was added. The reaction mixture was cooled to -5C and methyllithium in diethoxymethane (3.1 M, 11.6 mL, 36 mmol) was added. The reaction mixture was stirred at 45C for 4 hours. Sodium sulfate decahydrate (11.7 g, 36 mmol) was added at room temperature, the mixture was stirred 1.5 hours at 60C, diluted with water (100 mL) and after 30 minutes the precipitate was filtered off. The precipitate was dissolved in aqueous HC1 2M (100 mL) and ethyl acetate (140 mL). The biphasic system was filtered, the phases were separated and the pH of the water layer adjusted to 7 with aqueous NaOH 32% (18 mL). The precipitate was filtered and dried. The solid obtained was digested twice in methanol (20 mL) at room temperature. The two filtrates were combined, evaporated and dried under high vacuum to afford 6-chloro-4-methyl-pyridazin-3-amine (1.2 g, 58.1%) as a red solid. (0299) -NuMuRhonu (CDCb, 600 MHz): 7.09 (d, 1H); 4.90 (br s, 2H), 2.17 (d, 3H), 446273-59-2

446273-59-2 3-Amino-4-bromo-6-chloropyridazine 22024419, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ADAM, Jean-Michel; FANTASIA, Serena Maria; FISHLOCK, Daniel Vincent; HOFFMANN-EMERY, Fabienne; MOINE, Gerard; PFLEGER, Christophe; MOESSNER, Christian; (73 pag.)WO2019/57740; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-Bromo-6-chloro-pyridazin-3-amine (5.2 g, 25 mmol) was combined with tetrakis(triphenylphosphine)palladium(0) (700 mg, 0.61 mmol) and DMF (50 mL). To the mixture was added dimethylzinc in heptane (50 mL, 50 mmol, 1.0 M) at room temperature. The mixture was heated at 50 C for 2 h then 70 C for 1 h. The mixture was cooled to 0 C and excess reagent was quenched by the addition of H20. The mixture was filtered over Celite and concentrated. The residue was chromatographed on silica gel, eluting with 0-10% MeOH in CH2C12. MS m/z 144.2, 146.2 [M+H]+.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-bromo-6-chloro-pyridazin-3-amine (3.0 g, 14.4 mmol) and (0298) tetrakis(triphenylphosphine)palladium (1666 mg, 144 muiotaetaomicron) were suspended in THF (13.2 g) and a solution of zinc chloride in Me-THF (2.0 M, 9 mL, 18 mmol) was added. The reaction mixture was cooled to -5C and methyllithium in diethoxymethane (3.1 M, 11.6 mL, 36 mmol) was added. The reaction mixture was stirred at 45C for 4 hours. Sodium sulfate decahydrate (11.7 g, 36 mmol) was added at room temperature, the mixture was stirred 1.5 hours at 60C, diluted with water (100 mL) and after 30 minutes the precipitate was filtered off. The precipitate was dissolved in aqueous HC1 2M (100 mL) and ethyl acetate (140 mL). The biphasic system was filtered, the phases were separated and the pH of the water layer adjusted to 7 with aqueous NaOH 32% (18 mL). The precipitate was filtered and dried. The solid obtained was digested twice in methanol (20 mL) at room temperature. The two filtrates were combined, evaporated and dried under high vacuum to afford 6-chloro-4-methyl-pyridazin-3-amine (1.2 g, 58.1%) as a red solid. (0299) -NuMuRhonu (CDCb, 600 MHz): 7.09 (d, 1H); 4.90 (br s, 2H), 2.17 (d, 3H), 446273-59-2

446273-59-2 3-Amino-4-bromo-6-chloropyridazine 22024419, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ADAM, Jean-Michel; FANTASIA, Serena Maria; FISHLOCK, Daniel Vincent; HOFFMANN-EMERY, Fabienne; MOINE, Gerard; PFLEGER, Christophe; MOESSNER, Christian; (73 pag.)WO2019/57740; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-Bromo-6-chloro-pyridazin-3-amine (5.2 g, 25 mmol) was combined with tetrakis(triphenylphosphine)palladium(0) (700 mg, 0.61 mmol) and DMF (50 mL). To the mixture was added dimethylzinc in heptane (50 mL, 50 mmol, 1.0 M) at room temperature. The mixture was heated at 50 C for 2 h then 70 C for 1 h. The mixture was cooled to 0 C and excess reagent was quenched by the addition of H20. The mixture was filtered over Celite and concentrated. The residue was chromatographed on silica gel, eluting with 0-10% MeOH in CH2C12. MS m/z 144.2, 146.2 [M+H]+.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

446273-59-2, 3-Amino-4-bromo-6-chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,446273-59-2

6-Chloro-4-methylpyridazin-3-amineA 100 mL flask was charged with 4-bromo-6-chloropyridazin-3-amine (1 g, 4.80 mmol), dimethylzinc (9.59 mL, 9.59 mmol), Pd(PPh3)4 (0.277 g, 0.240 mmol) and DMF (10 mL). The reaction mixture was stirred at RT. Then the reaction mixture was quenched with MeOH and concentrated. The crude product was loaded onto a 10 g SCX SPE, and 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH were added. The fractions were combined and concentrated to afford 6-chloro-4-methylpyridazin-3-amine (693 mg, 80% yield).

446273-59-2 3-Amino-4-bromo-6-chloropyridazine 22024419, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

446273-59-2, 3-Amino-4-bromo-6-chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-bromo-6-chloro-pyridazin-3-amine (30.02 g, 143 mmol) and THF (180 mL) were charged into a reaction vessel. Methylmagnesium chloride (22% in THF, 50.0 mL, 1.03 eq.) was added at 20C over 60 minutes, followed by zinc chloride in Me-THF (25%, 37 mL, 0.50 eq.) and palladium tetrakis(triphenyphosphine) (1.66 g, lmol%). The reaction mixture was heated to 50C and methylmagnesium chloride (22% in THF, 81 mL, 1.7 eq.) was added slowly. The reaction mixture was stirred at 50C until complete conversion, then at 10C for 14.5 hours and poured into a mixture of water (90 g), aqueous HCl 33% (52.5 g) and toluene (150 mL) maintained at 20-30C. The aqueous phase was separated and the organic phase was extracted with a solution of aqueous HCl 33% (2.0 g) and water (45 g). The aqueous layers were combined and washed with toluene (30 mL) twice and the pH was adjusted by addition of 25% aqueous ammonia solution. When a pH of 2.4 was reached, seeding crystals were added, the mixture was stirred further for 15 minutes and thereafter the pH was brought to 4.0. The suspension was stirred at 20C for 2 hours, the precipitate was filtered off, washed with water (20 mL) three times to afford crude 6- chloro-4-methyl-pyridazin-3-amine (29 g) as a brown solid. (0302) 29 g crude product was transferred to a reaction vessel and methanol (20 mL) was added. The mixture was refluxed for 30 minutes and 12 g water was added. The solution was cooled to 0C and stirred for 2 hours at this temperature. The precipitate was filtered off, washed with water three times and dried under reduced pressure at 40C to afford purified 6-chloro-4-methyl-pyridazin-3-amine (13.8 g, 66%) as a light brown solid. (0303) Alternative purification: (0304) 50 g crude 6-chloro-4-methyl-pyridazin-3-amine were dissolved in methanol (250 mL) and active charcoal (4.0 g) and diatomaceous earth (2.5 g) were added. The suspension was stirred at 45C for 1 hour, cooled to 30C and potassium hydrogenophosphate (2.1 g) was added. The suspension was stirred at 30C for another 90 minutes, filtered and the precipitate washed with methanol (100 mL). The filtrate was concentrated to a residual volume of 175 mL and water (120 mL) was added. The resulting suspension was heated to reflux affording a solution which was cooled to 20C resulting in a suspension. The precipitate was filtered off, washed with water (90 mL) and dried under reduced pressure to afford pure 6-chloro-4-methyl-pyridazin-3-amine (38 g, 76%) as a light yellow solid.

446273-59-2, As the paragraph descriping shows that 446273-59-2 is playing an increasingly important role.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ADAM, Jean-Michel; FANTASIA, Serena Maria; FISHLOCK, Daniel Vincent; HOFFMANN-EMERY, Fabienne; MOINE, Gerard; PFLEGER, Christophe; MOESSNER, Christian; (73 pag.)WO2019/57740; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.446273-59-2,3-Amino-4-bromo-6-chloropyridazine,as a common compound, the synthetic route is as follows.

4-bromo-6-chloro-pyridazin-3-amine (3.0 g, 14.4 mmol) and (0298) tetrakis(triphenylphosphine)palladium (1666 mg, 144 muiotaetaomicron) were suspended in THF (13.2 g) and a solution of zinc chloride in Me-THF (2.0 M, 9 mL, 18 mmol) was added. The reaction mixture was cooled to -5C and methyllithium in diethoxymethane (3.1 M, 11.6 mL, 36 mmol) was added. The reaction mixture was stirred at 45C for 4 hours. Sodium sulfate decahydrate (11.7 g, 36 mmol) was added at room temperature, the mixture was stirred 1.5 hours at 60C, diluted with water (100 mL) and after 30 minutes the precipitate was filtered off. The precipitate was dissolved in aqueous HC1 2M (100 mL) and ethyl acetate (140 mL). The biphasic system was filtered, the phases were separated and the pH of the water layer adjusted to 7 with aqueous NaOH 32% (18 mL). The precipitate was filtered and dried. The solid obtained was digested twice in methanol (20 mL) at room temperature. The two filtrates were combined, evaporated and dried under high vacuum to afford 6-chloro-4-methyl-pyridazin-3-amine (1.2 g, 58.1%) as a red solid. (0299) -NuMuRhonu (CDCb, 600 MHz): 7.09 (d, 1H); 4.90 (br s, 2H), 2.17 (d, 3H), 446273-59-2

446273-59-2 3-Amino-4-bromo-6-chloropyridazine 22024419, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ADAM, Jean-Michel; FANTASIA, Serena Maria; FISHLOCK, Daniel Vincent; HOFFMANN-EMERY, Fabienne; MOINE, Gerard; PFLEGER, Christophe; MOESSNER, Christian; (73 pag.)WO2019/57740; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem