Tag: M.W:100-200

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

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

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

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

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.

Step 3[00162j To a 350 mL nitrogen purged Schlenk flask containing Int2 (3.77 g, 20.47 mmol) was added phosphorus oxychloride (38 mL, 408 mmol). The vessel was sealed and heated to 100 C for 3.5 hours. The reaction was cooled to room temperature and the excess phosphorus oxychloride was removed in vacuo. The crude oil was dissolved into chloroform, re-concentrated and then poured into ice water, rinsing with ethyl acetate.The two layers were transferred to a separatory funnel, separated and the aqueous layer extracted 3x with ethyl acetate. The combined organic layers were washed twice with water and once with brine (saturated aqueous sodium chloride) and then dried over sodium sulfate, filtered, concentrated and then purified by automated chromatography (5- 90% EtOAc:hexanes), providing Int3 (3.64 g, 16.3 mmol). ?H NMR (400MHz, chloroform-d) oe 7.70 (s, 1H), 4.55 (qd, J=7.1, 1.1 Hz, 2H), 1.46 (td, J=7.2, 0.9 Hz, 3H). LC retention time 0.79 [J]. MS(E) m/z: 221 (MHj., 1352925-63-3

1352925-63-3 Ethyl 4,6-dihydroxypyridazine-3-carboxylate 69007765, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; TOKARSKI, John S.; KUMAR, Amit; WO2014/74661; (2014); 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

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

1352925-63-3, Ethyl 4,6-dihydroxypyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0177j A mixture 5-5 (3.38 g, 18.3 mmol) in POC13 (35 ml) was heated at 95 C for 5 hr.The excess POC13 was removed under vacuum, to the residue ice was added followed byethyl acetate. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated to give compound 5-6 as an oil (3.27 g), 1352925-63-3

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

Reference：
Patent; PORTOLA PHARMACEUTICALS, INC.; XU, Qing; SONG, Yonghong; PANDEY, Anjali; WO2015/123453; (2015); 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

Intermediate VIII6-Chloro-2,4-dimethyl-2H-pyridazin-3-one Methyl iodide (1.3 mL) was added to a mixture of 6-chloro-4-methyl-2H-pyridazin-3-one (2.70 g) and K2CO3 (3.40 g) in N,N-dimethylformamide (27 mL). The resulting mixture was stirred at ambient temperature overnight. Then, water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). After removal of the solvent, the title compound was obtained as a solid.Yield: 2.97 g (100% of theory); Mass spectrum (ESI+): m/z=159/161 (Cl) [M+H]+., 1834-27-1

1834-27-1 6-Chloro-4-methylpyridazin-3(2H)-one 164886, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/108578; (2012); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1352925-63-3, Ethyl 4,6-dihydroxypyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1352925-63-3, To a glass lined reactor were charged toluene (0 26 kg), sulfolane (3.4 kg), Compound 1 (1.0 kg) and PQCh (2.7 kg). The crude was cooled to 0 C. Triethylamine (0.89 kg) was charged, and the resulting crude mixture was heated to 65 C and aged till the reaction reached completion. The reaction mass was cooled to 5 C. In a separate reactor, water (7.5 kg) was charged and cooled to 5 C The reaction mass was added slowly to the water solution, maintaining the internal temperature below 5 C. Additional water (0 5 kg) was used to rinse the reactor and aid the transfer. The resulting mixture was agitated at 5 C for 3 hours, then extracted with MTBE three times (3 x 4 5 kg). The combined organic layers were washed sequentially with aqueous pH 7 buffer solution (5.0 L/kg, 15 wt% KH2PO4/K2HPO4) and ‘ater (2.5 kg). The erode was distilled under vacuum until total volume became approximately 3 L/kg ACN (2 x 6 3 kg) was added followed by additional distillations back to -3 L/kg. The crude was cooled to 20 C to afford Compound 2 as a 30-36 wt% solution in 90-95% yield.

The synthetic route of 1352925-63-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; ROBERTS, Daniel Richard; (0 pag.)WO2019/232138; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem