Heterocyclic Building Blocks-Pyridazine

108784-42-5, 6-Fluoropyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,108784-42-5

12. The starting material was prepared as follows: 6-amino-3-fluoropyridazine (1.15 mmoles; Footnote 6) and alpha’-chloro-alpha,alpha,alpha-trifluoro-m-xylene in the minimum of DMF were heated to 60 C. for 4 hours. Evaporation of the solvent and trituration of the residue with anhydrous ether gave 6-amino-3-fluoro-1-(3-trifluoromethylbenzyl)-pyridazinium chloride.

108784-42-5 6-Fluoropyridazin-3-amine 13719068, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; Imperial Chemical Industries plc; ICI Pharma; US5049558; (1991); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29049-45-4,6-Chloropyridazin-4-amine,as a common compound, the synthetic route is as follows.

To a stirred suspension of potassium tert-butoxide (7.80 g, 69.5 mmol) inl,4-Dioxane (50 mL) was added (R)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (5.20 mL, 41.7 mmol) at 0 C and the reaction mixture was stirred at 25 C for 1 h. under Nitrogen atmosphere. Then 6-chloropyridazin-4-amine (3 g, 23.16 mmol) was added to the reaction mixture and the resulting reaction mixture was stirred at 1 10 C for 16 h. (TLC System Ethyl acetate, Rf: 0.3). The reaction mixture was poured into ice cold water (40 ml) and extracted with EtOAc (2×80 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to get crude compound. The crude product was purified by flash column chromatography (Neutral alumina, Eluent: 65% Ethyl acetate in Pet ether) to afford the desired product (R)- 6-((2,2-dimethyl-l,3-dioxolan-4-yl)methoxy)pyridazin-4-amine (2.2 g, 9.66 mmol, 41.7 % yield) as an off white solid. LCMS (m/z): 226.05 [M+H]+, Rt = 1.00 min.

29049-45-4, 29049-45-4 6-Chloropyridazin-4-amine 14099144, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1834-27-1, 6-Chloro-4-methylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6-chloro-4-methylpyridazin-3-ol (Intermediate X17; 500 mg, 3.46mmol) in DCM (20.3 mL) and pyridine (1 mL, 3.46 mmol) was treated with (3,5-dimethoxyphenyl)boronic acid (1.26 g, 6.92 mmol), Cu(OAc)2 (1.26 g, 6.92 mmol), and pyridine 1-oxide (1 .32 g, 13.8 mmol). The resulting mixture was stirred open to the atmosphere overnight at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and filtered. The filtrate was washed with water (2 x 30 mL), and the organics were dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The crude residue was precipitated from MeOH to cleanly afford the title compound (780 mg, 80%). MS (apci) m/z = 281.1 (M+H), 283.0 [(M+H)+2] (with Cl pattern).

1834-27-1, The synthetic route of 1834-27-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1632-74-2, 3,6-Dimethylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 100 mL of round-bottom flask maintained in a nitrogen atmosphere, was placed a mixture of 3,6-dimethylpyridazine (700 mg, 6.473 mmol, 1 equiv) and Se02 (3591.14 mg, 32.364 mmol, 5.00 equiv) in pyridine (20 mL). The reaction mixture was stirred for 16h at 120C. After cooling to room temperature, the resulting mixture was concentrated under reduced pressure. Into above crude product was added water (30 mL) and the resulting mixture was stirred for 2h at room temperature. The solid was collected by filtration and washed with MeOH (3×10 mL). The filtrate was concentrated under reduced pressure. This resulted in pyridazine-3,6-dicarboxylic acid which was used in the next step directly.

1632-74-2, The synthetic route of 1632-74-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; THE SCRIPPS RESEARCH INSTITUTE; EXPANSION THERAPEUTICS, INC.; DISNEY, Matthew; BLIZZARD, Timothy, Allen; RZUCZEK, Suzanne; NDUNGU, John; VACCA, Joseph; JENNINGS, Andy; PUSHECHNIKOV, Alexei; (333 pag.)WO2019/99777; (2019); A2;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

5754-18-7, 1,2-Dihydro-4-methyl-3,6-pyridazinedione is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5754-18-7, 4-Methyl-1,2-dihydropyridazine-3,6-dione (9.48 g, 75.2 mmol) was suspended in phosphorus oxychloride (70 mL, 750 mmol) at ambient temperature under an atmosphere of N2 and then heated at gentle reflux for 4 h to give a golden yellow homogenous solution. The mixture was allowed to cool and excess phosphorous oxychloride was removed by vacuum distillation (14 mbar, 50-70 C). The residual viscous brown oil was slowly added to ice-cooled sat. NaHCO3 solution (200 mL) with vigorous stirring. The resulting heterogenous mixture was adjusted to pH 6 by the slow addition of solid NaHCO3 and then extracted with EtOAc (2 x 60 mL). The combined organic phase was washed with sat. NaCl solution (30 mL), dried (MgSO4) and evaporated to give the title compound (11.5 g, 70.8 mmol; 94%) as a yellow powder; mp 87-88C (from light petrol/diethyl ether); IR (KBr): 3054, 1567, 1434, 1351, 1326, 1145, 1121, 914, 720 cm-1. 1H NMR (200 MHz, CDCl3): delta 2.42 (3H, d, J = 1.0 Hz), 7.41 (1 H, q, J = 0.9 Hz); 13C NMR (50 MHz, CDCl3): 19.2 (CH3), 130.1 (CH-5), 140.7 (C-4), 155.6 (C-6), 157.3 (C-3); LRMS (EI) 162 ([M+]). Anal. calcd for C5H4Cl2N2: C, 36.84; H, 2.47; N, 17.19. Found: C, 36.93; H, 2.57; N, 17.48.

5754-18-7 1,2-Dihydro-4-methyl-3,6-pyridazinedione 79826, apyridazine compound, is more and more widely used in various fields.

Reference：
Article; Ochiai, Koji; Takita, Satoshi; Eiraku, Tomohiko; Kojima, Akihiko; Iwase, Kazuhiko; Kishi, Tetsuya; Fukuchi, Kazunori; Yasue, Tokutaro; Adams, David R.; Allcock, Robert W.; Jiang, Zhong; Kohno, Yasushi; Bioorganic and Medicinal Chemistry; vol. 20; 5; (2012); p. 1644 – 1658;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36725-28-7,6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

Example 1 (Intermediate Compound) (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one A slight modification on the procedure described in J.Med.Chem. (1990), 33(10), 2870-2875 was used as follows. A solution of sodium nitrite (1.7 g) in water (12.5 ml) was added slowly at 0-5 C. to a solution of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (5 g) in 1 M hydrochloric acid (75 ml). The resulting solution was stirred on ice bath for five minutes and then added slowly to a solution of tin(II)chloride dihydrate (17 g) in 1 M hydrochloric acid (150 ml) keeping the reaction temperature below 5 C. This solution was stirred on ice for forty minutes and then a solution of 50% NaOH (75 ml) was quickly added. The resulting mixture was stirred on ice bath until the temperature reached zero degrees Celsius. The crystals were filtered and washed with dilute ammonia. Yield: 5.0 g, 93%. HPLC: enantiomerically pure. 1H NMR (400 MHz, DMSO-d6): delta=1.04 (d, 3H, CH3), 2.17 (d, 1H, J=16 Hz), 2.60 (m, 1H), 3.29 (m, 1H), 4.04 (s, 2H, NH2), 6.77 (d, 2H, J=8 Hz), 7.09 (b, 1H, NH), 7.54 (d, 2H, J=8 Hz), 10.66 (s, 1H, NHCO)., 36725-28-7

As the paragraph descriping shows that 36725-28-7 is playing an increasingly important role.

Reference：
Patent; Pystynen, Jarmo; Pippuri, Aino; Luiro, Anne; Nore, Pentii; Backstrom, Reijo; Lonnberg, Kari; Haikala, Heimo; Levijoki, Jouko; Kaheinen, Petri; Kaivola, Juha; US2003/158200; (2003); 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.1352925-63-3,Ethyl 4,6-dihydroxypyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

In a 5000 ml rb flask, ethyl 4,6-dihydroxypyridazine-3-carboxylate (200 g, 1086 mmol) was dissolved in THF (2000 mL), methanol (1000 mL) and water (800 mL). LiOH (137 g, 3258 mmol) was added slowly at rt and stirred at rt for 3-4 hr. The starting material was gone. The solvent was removed at 50 C. under reduced pressure to afford a yellow solid. The solid was acidified with aqueous HCl solution (400 ml) (1:1 ratio) at 0 C. and stirred at rt for 30-40 minutes. The solid was filtered and washed with water. It was then dried under vacuum for 1-2 hr. This solid was taken into 300 ml of methanol:DCM (2:8) and stirred at rt for 20-25 minutes. The mixture was filtered and the solid was washed with methanol and dried under vacuum for 1 hr. The desired product was obtained as a yellow solid, 4,6-dihydroxypyridazine-3-carboxylic acid (153 g, 951 mmol, 88% yield). MS (M+1) m/z: 156.9 (MH+). LC retention time 0.31 min [A]. 1H NMR (400 MHz, deuterium oxide) delta 6.00-5.34 (m, 1H), 4.75 (s, 7H)

1352925-63-3, As the paragraph descriping shows that 1352925-63-3 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Chunjian; Yang, Michael G.; Xiao, Zili; Chen, Ling; Moslin, Ryan M.; Tokarski, John S.; Weinstein, David S.; (84 pag.)US2019/152948; (2019); 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.108784-42-5,6-Fluoropyridazin-3-amine,as a common compound, the synthetic route is as follows.

6-Fluoropyridazin-3-ylamine (10 g, 89 mmol) was combined with a 50% (w/v) aqueous solution of chloroacetaldehyde (23 mL, 177 mmol) in n-butanol (150 mL) and stirred at reflux for 1h. The cooled reaction solution was reduced in volume and diluted with diethyl ether to precipitate a brown solid, which was collected by filtration, to yield 12.0 g of the titled compound. LRMS (ESI) m/z 138.0[(M+H)]+,calc?d for C6H4FN3: 137.12., 108784-42-5

108784-42-5 6-Fluoropyridazin-3-amine 13719068, apyridazine compound, is more and more widely used in various fields.

Reference：
Article; Kostich, Walter; Hamman, Brian D.; Li, Yu-Wen; Naidu, Sreenivasulu; Dandapani, Kumaran; Feng, Jianlin; Easton, Amy; Bourin, Clotilde; Baker, Kevin; Allen, Jason; Savelieva, Katerina; Louis, Justin V.; Dokania, Manoj; Elavazhagan, Saravanan; Vattikundala, Pradeep; Sharma, Vivek; Das, Manish Lal; Shankar, Ganesh; Kumar, Anoop; Holenarsipur, Vinay K.; Gulianello, Michael; Molski, Ted; Brown, Jeffrey M.; Lewis, Martin; Huang, Yanling; Lu, Yifeng; Pieschl, Rick; O’malley, Kevin; Lippy, Jonathan; Nouraldeen, Amr; Lanthorn, Thomas H.; Ye, Guilan; Wilson, Alan; Balakrishnan, Anand; Denton, Rex; Grace, James E.; Lentz, Kimberley A.; Santone, Kenneth S.; Bi, Yingzhi; Main, Alan; Swaffield, Jon; Carson, Ken; Mandlekar, Sandhya; Vikramadithyan, Reeba K.; Nara, Susheel J.; Dzierba, Carolyn; Bronson, Joanne; Macor, John E.; Zaczek, Robert; Westphal, Ryan; Kiss, Laszlo; Bristow, Linda; Conway, Charles M.; Zambrowicz, Brian; Albright, Charles F.; Journal of Pharmacology and Experimental Therapeutics; vol. 358; 3; (2016); p. 371 – 386;,
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