Category: pyridazine

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

To a glass lined reactor were charged toluene (0.26 Kg), sulfolane (3.4 Kg), compound 1 (1.0 Kg) and POCh (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 reaction reached completion. The reaction mass was cooled to 5 C. (0162) 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 aq pH 7 buffer solution (5.0 L/Kg, 15 wt% KH2PO4/K2HPO4) and water (2.5 Kg). The crude 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

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; CHEN, Ke; DEERBERG, Joerg; LIN, Dong; DUMMELDINGER, Michael; INANKUR, Bahar; KOLOTUCHIN, Sergei V.; LI, Jun; ROGERS, Amanda J.; ROSSO, Victor W.; SIMMONS, Eric M.; SOUMEILLANT, Maxime C. D.; TREITLER, Daniel S.; WANG, Jianji; ZHENG, Bin; SMITH, Michael J.; STROTMAN, Neil A.; TYMONKO, Steven; BENKOVICS, Tamas; (43 pag.)WO2018/183649; (2018); A1;,
Pyridazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35857-93-3,3,6-Dichloropyridazine-4-carbonitrile,as a common compound, the synthetic route is as follows.

[C] 5-Chloro-1H-pyrazolo [3 4-c] pyridazin-3-amine[0183][0184]To a stirred solution of 3 6-dichloropyridazine-4-carbonitrile (63 g 0.362 mol) in ethanol (700 mL) was added hydrazine hydrate (54.3 g 1.086 mol) andthe reaction mixture was stirred at 78 for 4 h. After the solvent was removed under reduced pressure the residue was diluted with water (50 mL) . The solution was filtered and the filter cake was washed with water (50 mL) and petroleum ether (100 mL) . The solid was collected to afford the title compound (25 g 73yield) as a yellow solid.1H NMR (400 MHz DMSO-d6) delta 8.24 (s 1H) 8.42-8.35 (m 1H) 6.09 (s 2H) .

35857-93-3, 35857-93-3 3,6-Dichloropyridazine-4-carbonitrile 12370915, apyridazine compound, is more and more widely used in various fields.

Reference：
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; CUMMING, John Graham; LIU, Yongfu; WU, Jun; WANG, Lisha; SHEN, Hong; SHI, Tianlai; (90 pag.)WO2017/133665; (2017); A1;,
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65632-62-4, (S)-1-((Benzyloxy)carbonyl)hexahydropyridazine-3-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,65632-62-4

a) Esterification of the Acid Function; The hexahydropyridazinic acid (40 g; 0.151 mol) is dissolved in 200 ml of methanol and cooled to 0 C. SOCl2 (36 ml; 0.45 mol) is added dropwise. The solution becomes clear; the temperature is allowed to return very gradually to ambient temperature and the solution is then refluxed for one hour. The mixture is poured onto a DCM(200 ml)/ice(500 g)/NaHCO3(60 g) mixture. The aqueous phase is extracted with DCM. The organic phase is washed with a saturated NaHCO3 solution and then dried over MgSO4. A colorless oil (41 g; 99%) is obtained and is used as it is.

As the paragraph descriping shows that 65632-62-4 is playing an increasingly important role.

Reference：
Patent; Aventis Pharma S.A.; US2005/171346; (2005); 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.1834-27-1,6-Chloro-4-methylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

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, As the paragraph descriping shows that 1834-27-1 is playing an increasingly important role.

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

57041-95-9, 6-Aminopyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57041-95-9, Step 32.1: 6-amino-2-methylpyridazin-3(2H)-one A mixture of 6-aminopyridazin-3-ol (2 g, 18.00 mmol), NaOH (0.720 g, 18.00 mmol) and MeI (1.126 mL, 18.00 mmol) was stirred for 2.5 hr at 85 C. under Ar. The reaction mixture was concentrated. The crude material was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 4-7%) to afford the title product (538 mg, 4.30 mmol, 24% yield) as a yellow solid. tR: 0.25 min (LC-MS 2); ESI-MS: 126 [M+H]+ (LC-MS 2); Rf=0.36 (CH2Cl2/MeOH 9:1).

As the paragraph descriping shows that 57041-95-9 is playing an increasingly important role.

Reference：
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; US2014/349990; (2014); A1;,
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Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1632-74-2,3,6-Dimethylpyridazine,as a common compound, the synthetic route is as follows.

Step B: A mixture of 3,6-dimethylpyridazine (81 mg, 0.75 mmol) and 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (143 mg, 0.5 mmol, prepared in Example 36, Part 2) in anhydrous CH3CN (1 mL) was stirred at room temperature for 5 d in a sealed tube to afford 1-(2-(7-fluoro-2-oxo-2H-chromen-3-yl)-2-oxoethyl)-3,6-dimethylpyridazin-1-ium bromide as a crude mixture in CH3CN.

1632-74-2, As the paragraph descriping shows that 1632-74-2 is playing an increasingly important role.

Reference：
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
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Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33097-39-1,3,6-Difluoropyridazine,as a common compound, the synthetic route is as follows.

(1) A mixture of 3,6-difluoropyridazine (7.8 g) and 25 ml of concentrated ammonium hydroxide solution is heated in a sealed tube for 2 hours at 70 C. After cooling, the crystals separated are filtered and washed with water to give 4 g of 3-amino-6-fluoropyridazine. NMR spectrum (d6 -DMSO)delta: 6.23 (2H, br. s), 7-7.2 (2H, m).

33097-39-1, As the paragraph descriping shows that 33097-39-1 is playing an increasingly important role.

Reference：
Patent; Takeda Chemical Industries, Ltd.; US4864022; (1989); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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

6-Fiuoro-pyridazin-3-ylamine [108784-42-5] (10 g, 89 mmol) was combined with a 50% (wjv)aqueous solution of chloroacetaldehyde [107-20-0] (23 ml, 177 mmol) inn-butanol (150 ml) and stirred at reflux for 1h. The cooled reaction solution was reduced in volume and diluted with diethylether to precipitate a brown solid, which was collected by filtration, to yield 12.0 g. LRMS (ESI) mjz138.0 [(M+H)J+, calc’d for CGH4FN3: 137.12.

108784-42-5, The synthetic route of 108784-42-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (2013); A1;,
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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.

Synthesis of 5-bromo-3-chloropyridazine. To a solution 6-chloropyridazin-4-amine (2 g, 15 mmol), t-BuONO (2.4 g, 23 mmol) in MeCN (40 mL) was added CuBr2 (5 g, 23 mmol) at 0 C. The resulting mixture was stirred at RT for 16 h and then concentrated in vacuo. The mixture was diluted with EtOAc (50 mL) and added H2O (50 mL). After filtered through celite, the filtrate was extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product which was purified by silica gel chromatography (PE/EA=20/1) to give 5-bromo-3-chloropyridazine (1.32 g, yield: 43%) as a brown oil. ESI-MS [M+H]+: 192.8, 194.8., 29049-45-4

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

Reference：
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (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.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