Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88497-27-2,3-Amino-6-bromopyridazine,as a common compound, the synthetic route is as follows.

88497-27-2, Step 1. Preparation of 6-(1-Methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-pyridazin-3-ylamine In a 15 mL microwave reaction vial was added potassium phosphate tribasic (1.43 g, 6.74 mmol), 6-bromopyridazin-3-amine (335 mg, 1.93 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridinium chloride (500 mg, 1.93 mmol), X-PHOS (138 mg, 289 mumol) and bis(dibenzylideneacetone)palladium (83 mg, 144 mumol) in 7 mL n-butanol and 1.4 mL H2O. The tube was sealed under argon and heated at 115 C. in oil bath for 3 hrs then stirred at room temperature overnight. The phases were separated and the aqueous was extracted with EtOAc.(10 ml). Water (20 mL) was added to the residual aqueous phase and was extracted with DCM (3*10 mL). The extracts were combined with the EtOAc organic phase. The resultant solution was absorbed onto silica gel and purified by LC chromatography eluting with 0-10% (10% NH4OH in MeOH) in 1/1 EtOAc/hexane to afford 300 mg (82%) of the title compound.

88497-27-2 3-Amino-6-bromopyridazine 2794779, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Berthel, Steven Joseph; Billedeau, Roland Joseph; Brotherton-Pleiss, Christine E.; Firooznia, Fariborz; Gabriel, Stephen Deems; Han, Xiaochun; Hilgenkamp, Ramona; Jaime-Figueroa, Saul; Kocer, Buelent; Lopez-Tapia, Francisco Javier; Lou, Yan; Orzechowski, Lucja; Owens, Timothy D.; Tan, Jenny; Wovkulich, Peter Michael; US2012/40949; (2012); A1;,
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141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5L, 3-neck flask was charged with 500.Og (3.356 moles) of 2,6-dichloropyridazine, followed by 1000 mL of methanol. The resulting pale yellow solution was treated with 2300 mL of a 25% (by weight) solution OfNaOCH3 in methanol over 3 hr. The resulting mixture was heated at gentle reflux for 20 hr. Afterward, the mixture was cooled to 4O0C and poured into 6000 mL water/2000 mL CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2×1 L). The combined organics were then dried over MgSO4 to give a white crystalline solid. The solid was further dried in vacuo to give the title compound (458.3g ;97.5% yield). NMR spectrum (DMSO) delta ppm 3.94 (s, 6H) 7.17 (s,2H).

141-30-0, 141-30-0 3,6-Dichloropyridazine 67331, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ALHAMBRA, Cristobal; CHANG, Hui-Fang (Amy); CHAPDELAINE, Marc; HERZOG, Keith, John; SCHMIESING, Richard, J; WO2011/21979; (2011); A1;,
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5469-70-5, 3-Aminopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5469-70-5, General procedure: Isopropylmagnesium chloride (2.0 M solution in THF, 6.23 mL, 12.5 mmol) was added to a solution the amine(13.0 mmol) in THF (90 mL). After stirring for several minutes, the solution was quickly transferred to a flask containing (2S,4S)-methyl 1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-4-fluoropyrrolidine-2-carboxylate (2.59 mmol). The reaction was stirred overnight at rt, then quenched with sat aq NH4Cl (150 mL). The mixture was extracted with EtOAc (150 mL), and the organics were washed with water (3 ¡Á 150 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified via a silica gel column (0-35% 90:10:1 [CH2Cl2/MeOH/NH4OH]/CH2Cl2), then by preparative HPLC (Waters Atlantis 30 ¡Á 100 mm, 0-70% 9:1 [MeOH/H2O 0.1% TFA]/1:9 [MeOH/H2O 0.1% TFA]). Product-containing fractions were concentrated on a Waters Oasis MCX cartridge, rinsed with MeOH, then eluted with 2 N NH3/MeOH. The eluent was concentrated in vacuo to obtain the desired product.

The synthetic route of 5469-70-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ross-Macdonald, Petra; De Silva, Heshani; Patel, Vishal; Truong, Amy; He, Aiqing; Neuhaus, Isaac; Tilford, Charles; Ji, Ruiru; Siemers, Nathan; Greer, Ann; Carboni, Joan; Gottardis, Marco; Menard, Krista; Lee, Frank; Dodier, Marco; Frennesson, David; Sampognaro, Anthony; Saulnier, Mark; Trainor, George; Vyas, Dolatrai; Zimmermann, Kurt; Wittman, Mark; Bioorganic and Medicinal Chemistry; vol. 20; 6; (2012); p. 1961 – 1972;,
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20744-39-2, Pyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 104- Bromo-5-methyl-2-[(phenylmethyl)oxy]-N-4-pyridazinylbenzamide (E10)4- Aminopyridazine (53.3 mg, 0.56 mmol), diisopropylethylamine (0.16 ml, 0.93 mmol) and HATU (266 mg, 0.70 mmol) were added to a solution of 4-bromo-5-methyl-2- [(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 12; 150 mg, 0.47 mmol) in N,N-dimethylformamide (3 ml). The mixture was stirred overnight. The solid was filtered and washed with water (2 ml) and methanol (3 ml) to give the product as a white solid (80 mg). A 2nd crop was obtained (33 mg). The crops were combined to yield the title compound as a white solid. 113 mg.MS (electrospray): m/z [M+H]+ 398/4001 H NMR (DMSO-de): 2.34 (3 H, s), 5.25 (2 H, s), 7.25 – 7.41 (3 H, m), 7.48 (2 H, dd, J=7.67, 1.53 Hz), 7.57 (1 H, s), 7.64 (1 H, s), 7.99 (1 H, dd, J=5.92, 2.63 Hz), 9.05 (1 H, dd, J=5.92, 1.10 Hz), 9.20 (1 H, dd, J=2.74, 0.99 Hz), 10.73 (1 H, s)

20744-39-2, 20744-39-2 Pyridazin-4-amine 298492, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
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141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of tert-butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate To a solution of 3,6-dichloropyridazine (Sigma-Aldrich, St. Louis, Mo.) (57.3 g, 385 mmol) in 1,4-dioxane (250 mL) were added tert-butyl piperazine-1-carboxylate (Sigma-Aldrich) (71.6 g, 358 mmol) and N,N-diisopropylethylamine (66.9 mL, 385 mmol). The mixture was stirred overnight at 80 C. then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (3 L) and washed with 10% citric acid, water, and brine. The organic layer was concentrated and the residue was re-crystallized in ethyl acetate to provide tert-butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate as an off-white solid (101 g, 88% yield). 1H NMR (400 MHz, CDCl3) delta ppm 1.25 (9H, s), 3.26-3.47 (8H, m), 6.67 (1H, d, J=9.6 Hz), 7.00 (1H, d, J=9.6 Hz); MS (ESI) m/z: 299.0 [M+H]+.

141-30-0, The synthetic route of 141-30-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; DU, Zhimei; MCCARTER, John Douglas; REDDY, Pranhitha; SNOWDEN, Andrew William; MCGEE, Lawrence R.; ALLEN, John Gordon; TREIBER, David Lawrence; KEEGAN, Kathleen; LI, Zhihong; US2015/353542; (2015); A1;,
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14161-11-6, 3,4,5-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,14161-11-6

To a solution of Intermediate I-09 (1.6 g, 8.72 mmol) in CH3CN (50 mL) was added a solution of Intermediate I-04 (2.04 g, 17.44 mmol) in CH3CN (50 mL). The reaction mixture was stirred at rt for 24 h, at 50C for 10 h, and at rt for 2 days. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (Biotage, cHex/EtOAc 80:20 to 0:100) to afford Intermediate 1-13 (1.20 g, 52%).HPLC-MS (method 4): Rt= 3.78 min, [M+H]+ m/z 264.1H NMR (300 MHz, CDCI3) delta 8.78 (s, 1H), 3.52 (s, 2H), 3.26 (s, 2H), 3.23 (s, 3H), 0.85 (s, 6H).

As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); MCNEENEY, Stephen, Phillip; PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; MARTIN HERNANDO, Jose Ignacio; RODRIGUEZ HERGUETA, Antonio; RICO FERREIRA, Maria del Rosario; BLANCO APARICIO, Carmen; WO2013/4984; (2013); A1;,
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20744-39-2, Pyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Furan-2-carboxylic acid pyridazin-4-ylamide (example 11.31 )2.00 g (17.8 mmol) of furan-2-carboxylic acid were suspended in 25 ml. of toluene and one drop of dimethylformamide was added to the mixture. 1 .95 ml of thionylchlo- ride (26.8 mmol) were added at room temperature and the reaction mixture was stirred at 80 C for two hours. After removal of the solvent, toluene was added and the evaporation was repeated. The obtained residue was then dissolved in 5 ml of dichloro- methane and the solution was added dropwise to a solution containing 1 .70 g of pyri- dazin-4-yl-amine (17.8 mmol) and 2.73 ml of triethyl amine (19.6 mmol) in 20 ml of di- chloromethane. The mixture was stirred at room temperature for 2 days and washed twice with water. The organic layer was dried over Na2S04, filtered and the solvent was removed under vaccum to give the title compound as a brown solid (1 .9 g, 54%, 95% purity). HPLC-MS: r.t. 1 .146 minutes, m/z [M+H+]189.9

20744-39-2, 20744-39-2 Pyridazin-4-amine 298492, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; BASF SE; LE VEZOUET, Ronan; SOeRGEL, Sebastian; DEFIEBER, Christian; GROss, Steffen; KOeRBER, Karsten; ANSPAUGH, Douglas D.; CULBERTSON, Deborah L.; WO2011/117198; (2011); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.38956-79-5,3-Hydrazinyl-6-methylpyridazine,as a common compound, the synthetic route is as follows.

General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 ¡Á 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

38956-79-5, 38956-79-5 3-Hydrazinyl-6-methylpyridazine 12379804, apyridazine compound, is more and more widely used in various fields.

Reference£º
Article; Ruso, Jayaraman Sembian; Rajendiran, Nagappan; Srinivas, Chowdappa; Murthy, Konappa Narasimha; Soumya, Krishnamurthy; Journal of the Korean Chemical Society; vol. 58; 4; (2014); p. 377 – 380;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

General procedure for chlorine substitution for different amines To a solution of 3,4,5-trichloropyridazine (1 eq) in MeOH (1 mL/mmol) was added dropwise a solution of the appropriate aminoalcohol (ex: 2-methylamino-ethanol) (3 eq) in MeOH (1 mL mmol) for 1h at RT. The solvent was removed in vacuo to give a brown oil which was purified by Biotage flash column chromatography (eluent: 70% EtOAc in cyclohexane to 100% EtOAc) to give the desired product (ex: 2-[(5,6-Dichloro-pyridazin-4-yl)-methyl-amino]-ethanol). Example: Synthesis of Intermediate 1-10 -pyridazin-4-yl)-methyl-amino]-ethanol: 1H NMR (300 MHz, CDCI3) delta 8.60 (s, 1H), 3.90 (t, J = 5.4 Hz, 2H), 3.72 (m, 2H), 3.20 (s, 3H).

14161-11-6, As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; BLANCO-APARICIO, Carmen; RODRIGUEZ-ARISTEGUI, Sonsoles; GOMEZ DE LA OLIVA, Cristina Ana; HERNANDEZ HIGUERAS, Ana Isabel; GONZALEZ CANTALAPIEDRA, Esther; AJENJO DIEZ, Nuria; WO2013/5057; (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.28682-70-4,Pyridazine-4,5-diamine,as a common compound, the synthetic route is as follows.

The mixture of intermediate 13 (4.6 g, 41.8 mmol, 1 eq.) and ethyl 2-oxoacetate (10.2 g, 50.1 mmol, 1.2 eq. 50% in toluene) in EtOH (240 ml) was stirred overnight at 80C. The solvent was removed under vacuum. The residue was reflux for 3 h in CH3CN, and then filtered to give pure intermediate 14 (3.07 g, yield 49.7%).

28682-70-4, As the paragraph descriping shows that 28682-70-4 is playing an increasingly important role.

Reference£º
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; DEMIN, Samuel Dominique; WO2014/114776; (2014); A1;,
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