Heterocyclic Building Blocks-Pyridazine

6082-66-2, 3,4,6-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Chlorobenzo[5, 6] [1, 4] dioxino[2, 3-c] pyridazine (51) To a suspension of sodium hydride (15.0 g, 375.0 mmol) in 1, 4-dioxane (400 mL) was added benzene-1, 2-diol (36.0 g, 320.0 mmol) and 3, 4, 6-trichloropyridazine (60.0 g, 320.0 mmol) under the ice-bath. The resulting solution was stirred at 100 C. for 10 h before quenched by the addition of saturated NaCl(aq) (100 mL). The resulting solution was extracted with ethyl acetate (3*500 mL) and the organic layers combined. Then the organic layer was washed with brine. The mixture was dried over anhydrous sodium sulfate and filtered. The residue was purified by flash column chromatography with ethyl acetate/petroleum ether (1:3) to afford 3-chlorobenzo[5, 6][1, 4] dioxino[2, 3-c] pyridazine (51) as a white solid (32.0 g, 50%). ESI-MS, m/z=221 [M+H]+.

The synthetic route of 6082-66-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tsai, Guochuan Emil; Wang, Ching-Cheng; Hsieh, Yuan-Ting; (53 pag.)US2019/112289; (2019); 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 3-amino-6-chloropyridazine (19.2 g,148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10% Pd catalyst on 1940 carbon (unreduced, 55% water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4CI. The organic layer was concentrated to give pyridazin-3-amine as a white solid (11 g, 78% yield). MS (APCI 10V) AP+1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6.95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2CI2 which was washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH/CH2CI2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70% yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz, DMSO-d6) delta ppm 7.20 – 7.24 (m, 2 H) 7.25 – 7.28 (m, 1 H) 7.39 – 7.44 (m, 2 H) 7.64 – 7.69 (m, 1 H) 8.05 (dd, 1 H) 8.94 (dd, 1 H) 11.34 (s, 1 H).

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

Reference£º
Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
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6082-66-2, 3,4,6-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(i) 2-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanol; A solution of ethylene glycol (55 ml) in tetrahydrofuran (200 ml) was treated at around 00C (ice bath cooling) with sodium hydride (60% dispersion in oil, 5.9 g) over 40 minutes. After the addition was complete, 3,4,6-trichloropyridazine containing isomers of bromo-dichloropyridazine as impurity (27 g) was added portionwise and washed in with more dry THF (50ml) and the mixture was stirred at 00C for 1 hour then at room temperature overnight. The mixture was concentrated (to 1/3 volume) then diluted with aqueous sodium bicarbonate solution and extracted with chloroform (5x) and ethyl acetate (3x). The combined organic extracts were washed with water, dried over sodium sulphate and evaporated and the solid filtered off and washed with CHCI3 (x3) and dried in a vacuum over overnight at 400C affording a white solid (25.5 g, 83%), containing some bromo-derivative (10-15%). MS (+ve ion electrospray) m/z 209/211 (MH+). MS (+ve ion electrospray) m/z 255/7 (MH+), bromo-derivative.

As the paragraph descriping shows that 6082-66-2 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2008/128961; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6082-66-2,3,4,6-Trichloropyridazine,as a common compound, the synthetic route is as follows.

Step 1: 3-(1-(3,6-dichloropyridazin-4-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole To a solution of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 200 mg; 0.59 mmol) in MeCN (10 mL) was added 3,4,6-trichloropyridazine (97 mg; 0.529 mmol) and K2CO3 (146 mg; 1.06 mmol) under nitrogen. The mixture was sirred at 85 C. for 24 hours, diluted with EtOAc (100 mL), washed with water (50 mL*3), brine (50 mL), dried over anhydrous Na2SO4, filtered, concentrated, and purified by reversed phase flash chromatography to afford 100 mg (39%) of the title compound a the yellow solid. LC-MS: m/z 488 [M+H]+. 1H NMR (400 MHz, CDCl3) delta [ppm]: 8.77 (s, 1H), 8.15 (s, 1H), 8.12 (s, 1H), 7.96 (s, 1H), 7.94 (s, 1H), 7.80 (dd, J=10.0, 2.4 Hz, 1H), 7.76 (s, 1H), 7.63-7.56 (m, 2H), 7.54-7.48 (m, 2H), 7.12 (td, J=8.8, 2.4 Hz, 1H).

As the paragraph descriping shows that 6082-66-2 is playing an increasingly important role.

Reference£º
Patent; Crosignani, Stefano; Cauwenberghs, Sandra; Deroose, Frederik; US2015/133422; (2015); 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

A 2-L round-bottom flask was charged with MeCN (600 ml) andchlorosulfonyl isocyanate (13.7 ml, 158 mmol)). The reaction mixture was cooled to 0 C in an ice-water bath before 2-bromoethanol (11.2 ml, 158 mmol) was added dropwise via syringe over 20 min. After 30 min, the yellow solution was allowed to warm to ambient temperature. After 1 h, pyridazin-3-amine (15 g, 158 mmol) and 4-methylmorpholine (69.4 ml, 631 mmol) were added in single portions to the stirred reaction mixture. The reaction vessel was equipped with a reflux adaptor. After 5 min, the reaction mixture was warmed to 50 C. After 16 h, the reaction mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. Aqueous HCI solution (0.5 M, 900 mL) and DCM (500 mL) were introduced and the layers were sperated. The aqueous layer was further extracted with DCM (4 x 300 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a tan solid. The solid was triturated in DCM (50 mL) and heptane 5 mL). The resulting suspension was filtered, and the collected solid was washed with heptane and DCM to afford 2-oxo-N-(pyridazin-3-yl)oxazolidine-3-sulfonamide (19.3 g, 39.7 mmol, 50.2 % yield) as a tan solid.

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

Reference£º
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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1632-76-4, 3-Methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of 6-methylpyridazine 1-oxideTo a solution of 3-methylpyridazine (4.60 g, 48.9 mmol) in acetic acid (30.0 mL) was added H202 (29.4 g,259 mmol, 29.4 mL, 30percent (w/w) in water). The mixture was heated at 120 ¡ãC for 6 h. The mixture wasallowed to cool to RT and poured in aqueous saturated NaHCO3 (500 mL) and extracted with DCM (5x 50 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo to afford 6- methylpyridazine 1-oxide (2.22 g, 20.2 mmol, 41percent). LCMS: caic. for [M+H] = 111.05, found 111.2. 1H- NMR shows a 1:1 mixture of both possible N-oxides.

1632-76-4 3-Methylpyridazine 74208, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; RATCLIFFE, Paul; CRAAN, Tobias; HERTRAMPF, Thorsten; LESCH, Bernhard; KIME, Robert; STEINHAGEN, Henning; WO2015/161928; (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.1121-79-5,3-Chloro-6-methylpyridazine,as a common compound, the synthetic route is as follows.

Intermediate A1 3-Methyl-6-[4-(methylsulfonyl)phenyl]pyridazineA suspension of 3-chloro-6-methylpyridazine (1.0 g, 7.78 mmol), (4-methylsulfonyl-phenyl)boronic acid (1.71 g, 8.56 mmol), Pd(PPh3)4 (450 mg, 0.39 mmol), potassium carbonate (2.69 g, 19.45 mmol) in 1,4-dioxane (25 mL) and water (5 mL) was heated at 95 C. overnight. Upon evaporation of the solvents, the residue was partitioned between water (150 mL) and chloroform (150 mL). The layers were separated and the water phase was extracted with chloroform (2 100 mL). The combined organic layers were evaporated and purified by flash chromatography (1:1 DCM/EtOAc, then 100% EtOAc). Yield 1.36 g (70%); Analytical HPLC: purity 99% (System A, RT=1.04 min); LRESIMS for C12H12N2O2S m/z 249 (M+H)+.

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

Reference£º
Patent; Biovitrum; US2008/58339; (2008); A1;,
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51149-08-7, 3,6-Dichloropyridazine-4-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 53-{6-Bromo-2-fluoro-3-[2-(1H-pyrazolo[3,4-c]pyridazin-3-yl)-ethyl]-phenoxy}-5-chloro-benzonitrile (I-5) Preparation of 3-(2,4-difluoro-phenoxy)-pyridazine-4-carboxylic acid (30b)step 1-To a solution of 28a (7.5 g, 38.9 mmol, Aldrich) in DCM (30 mL) and MeOH (10 mL) cooled to 0 C. was added slowly via pipette, a solution of (trimethylsilyl)diazomethane (2.0 M in hexane) until a persistent yellow color is observed. After addition was complete, the solvents were removed in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 25% EtOAc) to afford 3.89 g (86%) of 28b as a brown oil that solidifies on standing.

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

Reference£º
Patent; Roche Palo Alto LLC; US2008/293664; (2008); A1;,
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Pyridazine | C4H4N2 – PubChem

5096-73-1, 6-Chloropyridazine-3-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The compound 1 (the same as the compound described in Reference Example 1) (283 mg) was dissolved in DMF (3 ml), and 6-chloro-pyridazin-3-carboxylic acid (238 mg), HATU (760 mg) and diisopropylethylamine (348 mul) were added thereto. After the mixture was stirred all day and all night, water was added thereto, and then, the mixture was extracted with ethyl acetate. After the organic layer was washed sequentially with an aqueous 1N-sodium hydroxide solution, water and a saturated saline, the organic layer was dried with anhydrous sodium sulfate.After the organic layer was filtrated and concentrated, the residue was purified by the silica gel column chromatography, and the compound 2 (39.9 mg) was obtained.MS m/z 424/426 [M+H]+, APCI(+)

5096-73-1 6-Chloropyridazine-3-carboxylic acid 6415762, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; Mitsubishi Tanage Pharma Corporation; US2012/258951; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.135034-10-5,3-Chloro-6-iodopyridazine,as a common compound, the synthetic route is as follows.

Example 11 3-(4-[1,2,3]Triazol-1-yl-butyl)-6-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine 3-Chloro-6-iodo-pyridazine (11.56 g, 48.1 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (6.99 g, 57.7 mmol) and triethyl amine (NEt3) (94 ml) are dissolved in DMF (188 ml) and copper iodide (CuI) (0.981 g, 5.15 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium(0) (2.836 g, 2.43 mmol) is added and stirring is continued for 6 h at r.t. Dichloromethane (300 ml) is added, the mixture is washed with 0.5N hydrochloric acid (HCl) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate) yielding 3-chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine as a colorless solid. Yield 9.52 g (85%). 1H-NMR (400 MHz, CDCl3): delta=3.12 (t, 2H, CH2-C=), 4.67 (t, 2H, CH2-N), 7.39 (d, 1H, pyridazine), 7.45 (d, 1H, pyridazine), 7.70 (s, 1H, triazole), 7.73 (s, 1H, triazole).

The synthetic route of 135034-10-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bossenmaier, Birgit; Friebe, Walter-Gunar; Jenni, Wolfgang; Rueth, Matthias; Voss, Edgar; US2005/222228; (2005); A1;,
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