Heterocyclic Building Blocks-Pyridazine

41933-33-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.41933-33-9,2-Benzyl-4,5-dichloropyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

To a mixture of 2-benzyl-4,5-dichloropyridazin-3(2H)-one (30.6 g, 120 mmol), prepared as described in Example 244A, 4-chlorophenyl boronic acid (20.6 g, 132 mmol) and tetrakis(triphenylphosphine)palladium (5 g, 4.3 mmol) in toluene (300 mL) under an atmosphere of argon, and was added an aqueous Na2CO3 solution (2M, 66 mL, 132 mmol). The reaction mixture was stirred at 100 C. under argon for 16 h. The reaction was then allowed to cool to RT and was subsequently poured into water (200 mL). The resulting mixture was extracted with EtOAc (3¡Á150 mL). The combined organic layers were washed with saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained thick syrup was dissolved in MeOH (100 mL) and the resulting solution kept at 0 C. until white solid precipitated. The solid was collected by filtration, washed with hexanes, and then triturated with EtOAc-hexanes to give the title compound, 2-benzyl-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one (12 g, 30%) as a white powder. LC/MS (method A, general procedure): RT=3.81 min, (M+H)+=331.

The synthetic route of 41933-33-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yu, Guixue; Ewing, William R.; Mikkilineni, Amarendra B.; Pendri, Annapurna; Sher, Philip M.; Gerritz, Samuel; Ellsworth, Bruce A.; Wu, Gang; Huang, Yanting; Sun, Chongqing; Murugesan, Natesan; Gu, Zhengxiang; Wang, Ying; Sitkoff, Doree; Johnson, Stephen R.; Wu, Ximao; US2005/143381; (2005); A1;,
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5788-58-9,5788-58-9, 4,5-Dibromopyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred suspension of 4,5-dibromopyridazmn-3(2H)-one (4.00 g, 15.8 mmol) in methanol (40 mL, 990 mmol), was added potassium carbonate (4.00 g, 28.9 mmol) and the mixture was stirred at 80t for 67 hours. The solvent was removed in vacuum. Water was added to the residue and acetic acid was added until acidic pH was reached. A solid precipitated and wascollected by filtration, washed with water, and dried to give 2.23 g (69 % yield) of the title compound as a crude product.LC-MS (Method 5): R = 0.57 mm; MS (ESIpos): mlz = 205 [M+H]

As the paragraph descriping shows that 5788-58-9 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PREPARATION 2 SYNTHESIS OF 6-CHLOROPYRIDAZINE-3-CARBOXYLIC ACID To a mechanically stirred solution of 3-chloro-6-methylpyridazine (155.6 mmol) in 140 mL of concentrated sulfuric acid, finely powdered potassium dichromate (55.40 g) was added slowly, the temperature being kept below 50 C. When the addition was complete, stirring was continued for another 4 hours at 50 C. The viscous, dark green liquid was then cooled and crushed ice was added cautiously. The reaction mixture was extracted with ethyl acetate (6 x 400 mL). The ethyl acetate extracts were combined, dried over anhydrous Na2SO4. The solvent was concentrated in vacuo to yield slightly red colored 6-chloropyridazine-3-carboxylic acid (106.6 mmol). This material was used for next reaction without further purification. Yield 69%. m.p. 145C (dec). 1H NMR (300 MHz, DMSO-d6) delta 13.1, 8.20, 8.05., 1121-79-5

1121-79-5 3-Chloro-6-methylpyridazine 227254, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Xenon Pharmaceuticals Inc.; Abreo, Melwyn; Chafev, Mikhail; Chakka, Nagasree; Chowdhury, Sultan; Fu, Jian-Min; Gschwend, Heinz, W.; Holladay, Mark, W.; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Li, Wenbao; Liu, Shifeng; Raina, Vandna; Sun, Sengen; Sun, Shaoyi; Sviridov, Serguei; Tu, Chi; Winther, Michael, D.; Zhang, Zaihui; (94 pag.)EP2316827; (2016); B1;,
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867130-58-3, 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

867130-58-3, Step 10C: Ethyl 6-oxo-1,6-dihydropyridazine-4-carboxylate; The subtitle compound of step 10B was dissolved in EtOH (10 mL) and concentrated H2SO4 (4.2 mL) was added and then heated at reflux for 5 hours. The reaction mixture was cooled, concentrated in vacuo and basified with saturated Na2CO3. After filtration, the aqueous phase was extracted with ethyl acetate, dried over anhydrous Na2SO4, filtered and concentrated to give the subtitle compound (83%).1H NMR (400 MHz, MeOH-d4): delta 8.27 (d, 1H), 7.42 (d, 1H), 4.40 (q, 2H), 1.39 (t, 3H).

As the paragraph descriping shows that 867130-58-3 is playing an increasingly important role.

Reference£º
Patent; AstraZeneca AB; US2009/111821; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35857-89-7,6-Chloropyridazine-3-carbonitrile,as a common compound, the synthetic route is as follows.

Step 1) tert-butyl (1-(6-cyanopyridazin-3-yl)piperidin-4-yl)(methyl)carbamate To a solution of tert-butyl methyl(piperidin-4-yl)carbamate (605.8 mg, 2.83 mmol) and 6-chloropyridazine-3-carbonitrile (796.5 mg, 5.71 mmol) in EtOH (15 mL) was added Et3N (1.14 g, 11.30 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/1) to give the title compound as a yellow solid (252.0 mg, yield 28.1%). LC-MS (ESI, pos. ion) m/z: 318.0 [M+H]+; 1H NMR (400 MHz, CDCl3) delta (ppm): 7.45 (d, J=9.6 Hz, 1H), 6.87 (d, J=9.6 Hz, 1H), 4.68 (d, J=13.0 Hz, 2H), 4.33 (t, J=6.7 Hz, 1H), 3.11 (t, J=12.2 Hz, 2H), 2.73 (s, 3H), 1.85 (d, J=11.8 Hz, 2H), 1.71 (m, 2H), 1.50 (s, 9H)., 35857-89-7

As the paragraph descriping shows that 35857-89-7 is playing an increasingly important role.

Reference£º
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (78 pag.)US2016/229837; (2016); A1;,
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120276-59-7, 3-Chloro-6-(chloromethyl)pyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 121 5-(6-Chloro-pyridazin-3-ylmethyl)-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine (Compound 307) From 3-chloro-6-chloromethyl-pyridazine and 2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine following general procedure B. MS: 359.0 (M+H+); H1 NMR (DMSO-d6): delta(ppm) 10.45-10.54 (m, 1H), 9.67-9.73 (m, 1H), 8.11-8.19 (m, 1H), 7.97-8.15 (m, 2H), 7.66-7.79 (m, 1H), 7.40-7.52 (m, 1H), 6.35-6.42 (m, 2H).

120276-59-7, As the paragraph descriping shows that 120276-59-7 is playing an increasingly important role.

Reference£º
Patent; Genelabs Technologies, Inc.; US2009/226398; (2009); A1;,
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372118-01-9, Methyl 4,6-dichloropyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 3-dram vial were charged tert-butyl 2-(morpholin-3- yl)acetate (1.2 equiv.), methyl 4,6-dichloropyridazine-3-carboxylate (1.0 equiv.) and DMF (0.3 M). To the mixture at room temperature was added DIEA (3.0 equiv). The mixture was agitated in heating block at 70 C. After 5 h, the mixture was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtOAc/heptane) to afford the desired product methyl 4-(3 -(2-(tert-butoxy)-2-oxoethyl)morpholino)-6-chl oropyridazine3-carboxylate in 77% isolated yield. LCMS (m/z) (M+H) = 372.1, Rt = 1.25 mm.

372118-01-9, 372118-01-9 Methyl 4,6-dichloropyridazine-3-carboxylate 17848322, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
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1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Chloro-6-methylpyridazine (1.00 eq), 2-(dicyclohexylphosphino)biphenyl (0.05 eq), 2,4-bis(trifluoromethyl)phenylboronic acid (1.85 eq), 1,2-dimethoxyethane and aqueous potassium carbonate solution were all charged into a reactor. After degassing three times with nitrogen, palladium acetate (0.025 eq) was charged and the content is heated and agitated under reflux until the reaction was deemed complete.The reaction mixture was cooled to 22 C. Heptane was charged, followed by addition of Celite. After agitating for ca. 30 minutes at 22 C., the mixture was filtered into the first reactor, rinsing forward with a mixture of 1,2-dimethoxyethane and Heptanes. The layers of the filtrate are separated.To the organic layer was charged borane trimethylamine complex (0.03 eq), water, and acetic acid. The resultant mixture with a pH at maximum 4 was agitated for 1-2 h at 22 C. and then refluxed at ca. 80 C. for 2-3 h. After cooling back to 22 C., the mixture was adjusted to pH 10-11 with addition of 5% aq. sodium hydroxide while maintaining the content at 22 C. and then agitated for 1-2 h. The mixture was filtered and the layers were separated. The aq. layer was disposed of and the organic layer was filtered through ZetaCarbon cartridges into the in-process cleaned first reactor, rinsing forward with 1,2-dimethoxyethane through the carbon cartridges.The filtrate was concentrated under vacuum with a maximum jacket setting of 60 C. Heptane was charged and the contents were further concentrated under vacuum with a maximum jacket setting of 60 C. Additional Heptane was charged to the concentrate and the 1,2-dimethoxyethane (DME) content (maximum 0.5%) of the mixture was checked by NMR. After adjusting to 85 C. and agitating for ca. 1 h, the mixture was polished filtered hot through a filter into the second reactor.The filtrate in the second reactor was adjusted to reflux and then agitated for 1 h. With ramp cooling and moderate agitation, the mixture is cooled from reflux to 0 to 6 C. over a period of minimum 4 h and then agitated at 0 to 6 C. for 1 h.The product was filtered, washed with ambient temperature Heptanes and dried under vacuum at a maximum of 40 C. until loss on drying is maximum 1%. w/w Mole v/w Materials M.W. Ratio Ratio Ratio 2,4-Bis(trifluoromethyl)phenyl- 257.92 4.00 1.85 – boronic acid Borane trimethylamine complex 72.92 0.018 0.03 – 3-Chloro-6-methylpyridazine 128.56 1.00 1.00 – Diatomaceous earth (celite) N/A 0.30 – – Di(cyclohexyl)phosphinobiphenyl 350.49 0.14 0.05 – 1,2-Dimethoxyethane 90.12 12.00 – 13.80 Drinking water 18.02 3.75 – 3.75 Glacial acetic acid 60.05 0.05 0.10 – Heptanes 100.21 20.40 – 29.80 Palladium (II) acetate 224.49 0.044 0.025 – Potassium carbonate, 138.21 2.15 2.00 – Sodium hydroxide, 5% solution 40.00 – – –

1121-79-5, 1121-79-5 3-Chloro-6-methylpyridazine 227254, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Gilead Sciences, Inc.; K.U. Leuven Research & Development; Gerhard Puerstinger; US2009/36460; (2009); A1;,
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1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the commercially available starting material 101 in CHCl3, trichloroisocyanuric acid (TCCA) was added at 60 C. Then the solution was stirred for 1.5 hrs, cooled, and filtered with HiFlo-Celite. The filtrate was concentrated and dried with vacuum. The yield was 5.037 g of compound 102.

1121-79-5, The synthetic route of 1121-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong; US2013/273005; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5469-69-2,3-Amino-6-chloropyridazine,as a common compound, the synthetic route is as follows.

To a solution of 2 (875 mg, 6.76 mmol) and sodium hydroxide(304 mg, 6.76 mmol) in absolute ethanol (30 mL) stirred underargon was added Pd/C (131 mg, 1.23 mmol). The mixture was thenstirred at room temperature under hydrogen atmosphere and reaction progress was followed by TLC monitoring. After 20 h, themixture was filtered through a celite pad and the filtrate wasevaporated under reduced pressure. The crude product waswashed with Et2O to give compound 30 (700 mg, 100%) as a palepink solid.Mp 164.1 C. 1H NMR (300 MHz, CDCl3) d 8.58 (dd, 1H, J 4.5,1.5 Hz, H6), 7.23 (dd, 1H, J 9.0, 4.5 Hz, H5), 6.83 (dd, 1H, J 9.0,1.5 Hz, H4), 5.18 (bs, 2H, NH2). 13C NMR (75 MHz, CDCl3) d 159.5,144.1, 128.2, 114.6.

5469-69-2, As the paragraph descriping shows that 5469-69-2 is playing an increasingly important role.

Reference£º
Article; Moine, Esperance; Dimier-Poisson, Isabelle; Enguehard-Gueiffier, Cecile; Loge, Cedric; Penichon, Melanie; Moire, Nathalie; Delehouze, Claire; Foll-Josselin, Beatrice; Ruchaud, Sandrine; Bach, Stephane; Gueiffier, Alain; Debierre-Grockiego, Francoise; Denevault-Sabourin, Caroline; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 80 – 105;,
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