Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

To a 1000-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 6-chloro-2,3- dihydropyridazin-3-one (5 g, 38.30 mmol) and (3-methoxyphenyl)boronic acid (7.6 g, 50.01 mmol) in dioxane (300 mL)/water (15 mL) then Pd(dppf)Cl2 (1.41 g) and K2C03 (15.9 g, 115.04 mmol) were added. The reaction was stirred at 110C for 15 h, quenched by the addition of 100 mL of water, and extracted with EtOAc (3×150 mL). The organic extracts were combined, washed with brine (3×200 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (9: 1) affording 5.6 g (72%) of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for CnHnN202+: 203.1 (M+H); Found: 203.1., 19064-67-6

As the paragraph descriping shows that 19064-67-6 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; PARKS, Daniel; MUNOZ, Benito; (66 pag.)WO2018/81378; (2018); A1;,
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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

5788-58-9, To a stirred solution of (3S)-3-methyl-1-[(2-methylphenyl)methyl]piperazine (500 mg, 2.45 mmol, 1 equiv.) and DIEA(632.6 mg, 4.89 mmol, 2 equiv.) in DMA(5 mL) was added 4,5- dibromo-2,3-dihydropyridazin-3-one (745.6 mg, 2.94 mmol, 1.2 equiv.) in portions at 100 degrees C overnight

The synthetic route of 5788-58-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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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.51149-08-7,3,6-Dichloropyridazine-4-carboxylic acid,as a common compound, the synthetic route is as follows.

51149-08-7, 2,5-Dichloro-pyridizine-3-carboxylate (0.40 g, 2.07 mmol) in toluene (8 ML) was reacted with triethylamine (0.72 ML, 5.20 mmol) and benzyl amine (0.23 ML, 2.07 mmol) at 90 C. for 8 hours.The solution was partitioned between water and ethyl acetate.The organic layer was dried over sodium sulfate, filtered, and concentrated to yield the title compound (0.257 g, 47%). MS (DCI/NH3) m/z 264 (M+H+)+.

The synthetic route of 51149-08-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pemela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/87577; (2004); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5469-70-5,3-Aminopyridazine,as a common compound, the synthetic route is as follows.

A flask was charged with perfluorophenyl 1-(4-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (3.33 g, 5.78 mmol) and pyridazin-3-amine (0.659 g, 6.93 mmol). A septum was attached and THF (28.9 ml) was added. The mixture was cooled to 0 C. and a THF solution of lithium bis(trimethylsilyl)amide (12.13 ml, 12.13 mmol, 1 M) was added dropwise to give a brown solution. The solution was maintained at 0 C. for 20 min. The reaction mixture was partitioned between 1 N HCl (200 mL) and EtOAc (200 mL), the layers were separated and the aqueous layer was extracted with DCM (100 mL) and EtOAc (200 mL). The combined organic layers were dried (Na2SO4) and concentrated to provide 1-(4-bromo-2-methoxyphenyl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoline-6-sulfonamide (3.39 g, 6.96 mmol, 120% yield) as a light yellow foam. Although contaminated with solvent, the product was of sufficient purity for use in the next step. m/z (ESI) 485.1 (M-H)-.

5469-70-5, As the paragraph descriping shows that 5469-70-5 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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1837-55-4, 3,5-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In analogy to the preparation of the intermediate 8-1 (step 1) from tert-butyl N- [(lR,5S,8S)-3-azabicyclo[3.2.1]octan-8-yl]carbamate (2.00 g, 8.84 mmol) and 3,5- dichloropyridazine (2.0 g, 13.4 mmol) in a sealed tube at 90 C using EtOH as solvent in the presence of Et3N (3.63 g, 5.0 mL, 35.9 mmol), tert-butyl N-[(lR,5S,8S)-3-(6-chloropyridazin-4- yl)-3-azabicyclo[3.2.1]octan-8-yl]carbamate (1.71 g, 54%) was obtained as a white solid. MS (ES+) m/z: 339.2 [(M+H)+]., 1837-55-4

As the paragraph descriping shows that 1837-55-4 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; SARIE, Jerome Charles; VASTAKAITE, Greta; (61 pag.)WO2018/83050; (2018); 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.

5-Chloro–N2- (1,5- dimethyl -1H- pyrazol-3-yl) -N4- (3- ethyl-piperidin-4-yl) pyrimidine-2,4-diamine (0.12g , 0.34mmol) was suspended (10.OmL) at EtOH, to which was added 6-chloro-pyridazin-3-carbonitrile (96mg, 0.69mmol) and triethylamine (0.15mL, 1.10mmol). The reaction system was stirred at 40 overnight, then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (MeOH solution of DCM / 3M NH3 in the (v / v) = 100/1 to 75/1 to 50/1) to give the title compound as a yellow solid (45mg, yield 29% ).

35857-89-7, The synthetic route of 35857-89-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1120-95-2,3-Chloropyridazine,as a common compound, the synthetic route is as follows.

Example 4-5 (Trans)-8-({[6-(3,5-dimethylphenyl)-3-pyridazinyl]amino}methyl)-3-(3-pyridazinyl)-1-oxa-3-azaspiro[4.5]decan-2-one dihydrochloride (Trans)-8-({[6-(3,5-dimethylphenyl)-3-pyridazinyl]amino}methyl)-1-oxa-3-azaspiro[4.5]decan-2-one (Intermediate 46, 20 mg, 0.055 mmol), trans-1,2-diaminocyclohexane (0.013 ml, 0.109 mmol), 3-chloropyridazine (prepared according to WO/0107416, 12.50 mg, 0.109 mmol), K3PO4 (34.8 mg, 0.164 mmol), copper(I) iodide (10.39 mg, 0.055 mmol) were suspended in 1,4-dioxane (4 ml) and shaken at 120 C. in a closed vial overnight. The resulting dark mixture was concentrated under vacuum, taken up with DCM (20 ml) and filtered over a separation tube. The organic solution was concentrated and purified with Biotage SP1 over a 12S NH2 Varian cartridge, eluding with a gradient of cyclohexane and EtOAc. (Trans)-8-({[6-(3,5-dimethylphenyl)-3-pyridazinyl]amino}methyl)-3-(3-pyridazinyl)-1-oxa-3-azaspiro[4.5]decan-2-one was eluted with ca 70% EtOAc and recovered as a colourless oil (12 mg, 0.027 mmol, 49%). 1H NMR (400 MHz, CDCl3): delta 8.97 (dd, 1H), 8.58 (dd, 1H), 7.63-7.61 (m, 3H), 7.50 (dd, 1H), 7.07 (br s, 1H), 6.73 (d, 1H), 4.86 (br t, 1H), 4.23 (s, 2H), 3.46 (t, 2H), 2.41 (s, 6H), 2.12-1.07 (m, 9H); HPLC-MS: 1.69 min, 445 [M+H]+., 1120-95-2

As the paragraph descriping shows that 1120-95-2 is playing an increasingly important role.

Reference£º
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); A1;,
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20698-04-8, 3,6-Diiodopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method C3-(6-lodo-pyridazin-3-yl)-9-methyl-9-aza-bicvclor3.3.1lnonane free base (Intermediate compound; JBP 18097-a)A mixture of 9-methyl-3,9-diazabicyclo[3.3.1]nonane (4.0 g, 28.5 mmol), 3,6-diiodopyridazine (9.5 g, 28.5 mmol), diisopropylethylamine (7.4 g, 57.0 mmol) and dioxane (50 ml) was stirred at 750C for 4 days. Aqueous sodium hydroxide (75 ml, 1 M) was added, dioxane was evaporated and the mixture was extracted twice with dichloromethane (2 x 75 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. Yield 4.61 g (47%). Mp. 163-166C., 20698-04-8

The synthetic route of 20698-04-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEUROSEARCH A/S; WO2006/87306; (2006); A2;,
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Pyridazine | C4H4N2 – PubChem

144294-43-9, 3-Amino-5-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0388-1 A mixture of 6-chloro-N-(pyrimidin-5-yl)-1,5-naphthyridine-3-amine (10 mg), 5-methylpyridazine-3-amine (6.4 mg), tris(dibenzylideneacetone)dipalladium(0) (3.5 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4.5 mg), cesium carbonate (25 mg), and 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and the solid matter was collected by filtration, thereby obtaining N2-(5-methylpyridazin-3-yl)-N7-(pyrimidin-5-yl)-1,5-naphthyridine-2,7-diamine (1.6 mg). 1H-NMR(CDCl3/CD3OD=4/1) delta: 8.81 (1H, s), 8.75 (2H, s), 8.73 (1H, brs), 8.64 (1H, brs), 8.51 (1H, d, J=2.4 Hz), 8.12 (1H, d, J=9.0 Hz), 7.83 (1H, d, J=2.4 Hz), 7.36 (1H, d, J=9.0 Hz), 2.45 (3H, s). MS m/z (M+H): 331.

144294-43-9, The synthetic route of 144294-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
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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.

A mixture of 3,4,5-trichloropyridazine (0.250 g, 1.363 mmol), (2,3-dihydro-1H-inden-2-yl)methanamine hydrochloride (0.250 g, 1.363 mmol), and potassiumcarbonate (0.396 g, 2.86 mmol) in dioxane (10 ml) was heated to reflux for 1 h. The mixture was cooled and 35% hydrazine (2.469 ml, 27.3 mmol) was added. The mixture was heated to reflux for 16 h overnight. The reaction was diluted with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over5 magnesium sulfate, and concentrated to give 5-chloro-N-((2,3-dihydro-1H-inden-2- yl)methyl)-6-hydrazinylpyridazin-4-amine. LCMS: Rt = 1.85 mi (M+H7 = 290.1. The material was used without purification.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); A1;,
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