Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.65202-50-8,Methyl 6-chloropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

65202-50-8, Step 5; Methyl 6-(4-[2-(trifluoromethyl)benzoyl]piperazin-l-yUpyrida2ine-3-carboxylate; To a mixture of methyl -chloropyridazine-S-carboxylate (3.9 g, 22.6 mmol), l-[2- (trifluoromethyl)benzoyl]piperazine (7.0 g, 27.1 mmol) and potassium carbonate (6.5 g, 47 mmol) was added 100 mL of dioxane and the mixture was heated to reflux for 71 h. The mixture was cooled to room temperature and the solid filtered and swirled in 4: 1 ethepiethyl acetate at reflux for 45 min. The solid was filtered to provide the title compound.

The synthetic route of 65202-50-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK FROSST CANADA LTD.; WO2007/9236; (2007); A1;,
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15456-86-7, 4-Bromo-1,2-dihydropyridazine-3,6-dione is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a degassed solution of 4-bromo-1,2-dihydropyridazine-3,6-dione (100 mg, 0.5 mmol), (4-fluoro-1H-indol-2-yl)boronic acid (131 mg, 0.7 mmol) and K3P04 (279 mg, 1.1 mmol) in DMF (2 mL) and H20 (0.2 mL) was added Pd(dppf)Cl2 (5 mg) under N2. The mixture was stirred at 80 C for 12 h. After the solvent was removed, the residue was purified by prepTLC (DCM : EtOAc = 10: 1) to give the product of 4-(4-fluoro-1H-indol-2-yl)-1,2-dihydropyridazine-3,6-dione (50 mg, yield: 39%). ?H-NMR (DMSO-d6, 400 MHz,) 11.95 (br.s, 1H), 7.47-7.68 (m, 3H), 7.35 (d, J= 8.0 Hz, 1H), 7.1 1-7.19 (m, 1H), 6.81 (dd, J= 8.0, 10.4Hz, 1H). MS (M+H): 246., 15456-86-7

The synthetic route of 15456-86-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); 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 round bottom flask was charged with pyridazin-3 -amine (10.11 mg, 0.106 mmol) and DMSO (0.204 ml) to give a solution. (P)-perfluorophenyl l-(5-fluoro-2-methoxy- 4-(3,3,3-trifluoropropyl)phenyl)-2-oxo-l,2-dihydroquinoline-6-sulfonate (0.050 g, 0.082 mmol) and THF (0.613 ml) were added. The flask was cooled in an ice-bath for 5 minutes, then LHMDS (1M in THF) (0.188 ml, 0.188 mmol) was added dropwise. The reaction was stirred for 15 minutes. The reaction was diluted with ethyl acetate and washed twice with IN HC1 solution. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40g, gradient elution 10-75% [3: 1 EtOAc/EtOH]: Heptane) to afford (P)-l-(5-fluoro-2-methoxy-4- (3,3,3-trifluoropropyl)phenyl)-2-oxo-N-( yridazin-3-yl)-l,2-dihydroquinoline-6-sulfonamide (0.036 g, 0.069 mmol, 84 % yield) as a white solid. NMR (400 MHz, DMSO-i) delta = 2.62 – 2.79 (m, 2 H) 2.89 – 3.04 (m, 2 H) 3.66 (s, 3 H) 6.67 (d, J=8.86 Hz, 1 H) 6.76 (d, J=9.59 Hz, 1 H) 7.30 – 7.40 (m, 2 H) 7.68 (dd, J=9.43, 3.73 Hz, 1 H) 7.84 (d, J=7.98 Hz, 1 H) 7.93 (d, J=9.23 Hz, 1 H) 8.18 (d, J=9.64 Hz, 1 H) 8.25 – 8.38 (m, 2 H) 14.49 (br. s., 1 H). m/z (ESI) 523.0 (M+H)+., 5469-70-5

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

Reference£º
Patent; AMGEN INC.; WEISS, Matthew; MILGRAM, Benjamin C; MARX, Isaac E.; DINEEN, Thomas; (63 pag.)WO2017/106871; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1632-76-4,3-Methylpyridazine,as a common compound, the synthetic route is as follows.

To 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 00 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-methyl- pyridazine 1-oxide (2.22 g, 20.2 mmol, 41percent). LCMS: cal for [M+H} = 111.05, fd 111.2. 1H NMR shows a 1:1 mixture of both possible N-oxides.

1632-76-4, The synthetic route of 1632-76-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; RATCLIFFE, Paul; CRAAN, Tobias; HERTRAMPF, Thorsten; LESCH, Bernhard; STEINHAGEN, Henning; (70 pag.)WO2015/161924; (2015); A1;,
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19064-67-6, 6-Chloro-3-hydroxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-chloropyridazin-3 (2H)-one (0.140 g, 1.07 mmol), (3 -methylquinolin-7-yl)boronic acid, (0.221 g, 1.18 mmol), Cu(OAc)2 (0.0390 g, 0.215 mmol) and pyridine(0.191 ml, 2.36 mmol) in DCM (10.7 mL, 1.07 mmol) was stirred at room temperature overnight. The reaction mixture was partitioned between EtOAc and water. The organic extracts were washed with brine, then dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The resulting residue was purified by silica chromatography to afford the title compound (25 mg, 8.6% yield). MS (apci) m/z = 274.0 [(M+H)+2], 272.0 (M+H) with Cl pattern.

19064-67-6, 19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); A1;,
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289-80-5, Pyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The synthesis of 2 was similar to that of complex 1, but 3-nitrophthalic acid (H2npt) was used instead of H3btc. Reaction of AgNO3 (33.4 mg, 0.2 mmol), pyridazine (pdz)(16.0 mg, 0.2 mmol) and 1,3,5-benzene tricarboxylic (H3btc)(44.2 mg, 0.2 mmol) took place in H2O-DMF (N,N-Dimethylformamide)solvents (6 ml, v/v = 1:1) in the presence of ammonia(0.5 mL, 14 M) under ultrasonic treatment (160 W, 40 kHz,30 min) at 40 C. The resultant colourless solution was allowed slowly to evaporate at room temperature in the dark. The yellowcrystals of complex 1 were obtained after several days.The crystals were isolated by filtration and washed by deionized water and ethanol and dried in the air. And lightyellow crystals of 2 were obtained in 78% yield based on Ag. Elemental analysis: Anal. Calc. for Ag2C12H7N3O6: C, 28.545; H,1.397; N, 8.322. Found: C, 28.65; H, 1.41; N, 8.36%. Selected IR peaks (cm1): 3410 (m), 3085 (m), 2970 (w), 2849 (w), 1964 (w),1595 (s), 1519 (s), 1455 (s), 1372 (s), 1290 (s), 1156 (m), 1060(m), 965 (m), 920 (s), 819 (s), 787 (m), 748 (s), 710 (s), 684 (s),583 (w), 545 (w), 424(m)., 289-80-5

The synthetic route of 289-80-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Dan-Feng; Zhang, Ting; Dai, Si-Min; Huang, Rong-Bin; Zheng, Lan-Sun; Inorganica Chimica Acta; PA; (2014); p. 193 – 200;,
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35857-89-7, 6-Chloropyridazine-3-carbonitrile is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-chl oro-Af2-(3,8-di methyl i mi dazo[ l ,2-c/]pyridin-7-yl)-A – (piperidin-4-yl)pyrimidine-2, 4-diamine (100 mg, 0.2689 mmol) in ethanol (10 mL) were added 6-chloropyridazine-3-carbonitrile (56.5 mg, 0.405 mmol) and TEA (54.5 mg, 0.539 mmol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filter cake was washed with EtOH (50 mL x 3) to give the title product as a light yellow solid (98 mg, yield 76.73%).MS(ESI,pos.ion)m/z: 475.2 [M+H]+;1H NMR (400 MHz, DMSO-d6) d (ppm): 8.78 (s, 1H), 8.10 (d, j = 7.2 Hz, 1H), 7.91 (s, 1H), 7.85 (d, j = 9.6 Hz, 1H), 7.38 (t, j= 8.7 Hz, 2H), 7.32 (s, 1H), 6.89 (d, j= 7.7 Hz, 1H), 4.56 (d, j = 12.3 Hz, 2H), 4.21 (s, 1H), 3.05 (t, j = 12.5 Hz, 2H), 2.43 (s, 3H), 2.41 (s, 3H), 1.94 (d, j =I I .8 Hz, 2H), 1.69-1.53 (m, 2H)., 35857-89-7

35857-89-7 6-Chloropyridazine-3-carbonitrile 13382871, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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Pyridazine | C4H4N2 – PubChem

84956-71-8, 2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

84956-71-8, Preparation Example 23 Preparation of 2-t-butyl-4-chloro-5[{6-(4-fluorobenzyloxy)-3-pyridyl}-methyloxy]-3(2H)-pyridazinone (Compound No. 1011) To a solution of 2.3 g of 6-(4-fluorobenzyloxy)-3-pyridine methanol in 20 ml of N,N-dimethylformamide was added under stirring at 0C 0.5 g of 55% sodium hydride (in mineral oil). After stirring for 30 minutes at room temperature, thereto was added 2.2 g of 2-t-butyl-4,5-dichloro-3(2H)-pyridazinone. The reaction mixture was stirred at room temperature for additional 8 hours, poured into 50 ml of ice water and extracted twice with 50 ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to give 4.1 g of a crude product. The crude product was added with isopropyl ether and recrystallized therefrom to obtain 3.2 g of 2-t-butyl-4-chloro-5-[{6-(4-fluorobenzyloxy)-3-pyridyl}-methyloxy]-3(2H)-pyridazinone, m.p. 121.0 124.0C.

84956-71-8 2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one 2782225, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; NISSAN CHEMICAL INDUSTRIES LTD.; EP199281; (1991); B1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17973-86-3,3,6-Dibromopyridazine,as a common compound, the synthetic route is as follows.

[00207] To a solution of 3,6-dibromopyridazine (400 mg, 1.68 mMol, 1.0 eq.) in dry THF (19 ml_) at 10 C was added NaH (8.1 mg, 2.02 mMol, 1.2 eq., 60 % in mineral oil) and the reaction was stirred at 10 C for 10 min. A solution of (1-methyl-piperidin-4-yl)-methanol (239 mg, 1.85 mMol, 1.1 eq.) in dry THF (1 ml_) was added and the reaction was allowed to warm to RT and stirred at RT for 4.5 h then at 40 C for 16 h. The reaction was quenched with NaHCC>3 (aq.) and the THF removed under reduced pressure. The aqueous phase was extracted with ethyl acetate (3x) and the combined organic phases washed with brine, dried (MgSCU) and concentrated to give a white solid. The crude material was purified by silica column chromatography eluting with 0-10 % methanol/DCM to give the desired product as a white solid (183 mg, 0.64 mMol, 38 %). AnalpH9_MeOH_4MIN: Rt: 2.45 min, m/z 286.2/288.1 [M+H]+

17973-86-3, The synthetic route of 17973-86-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (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.19064-64-3,3,6-Dichloro-4-methylpyridazine,as a common compound, the synthetic route is as follows.

Step 9.1. 6-Chloro-4-methylpyridazin-3-ylamine and 6-chloro-5-methylpyridazin-3-ylamine A mixture of 50.0 g (307 mmol) of 3,6-dichloro-4-methylpyridazine in 170 ml of aqueous ammonia (30%) is heated at 120 C. for 16 h in a steel reactor at the internal pressure of bar.The reactor is cooled and the reaction mixture is poured into 200 ml of water. The solid formed is isolated by filtration and dried under vacuum, to give 38.5 g of a mixture containing approximately 45% of 6-chloro-4-methylpyridazin-3-ylamine (CAS 64068-00-4) and 55% of 6-chloro-5-methylpyridazin-3-ylamine (CAS 66346-87-0).1H NMR (CDCl3) delta: 7.20 and 6.75 (2s, 1H): (d, 0.55H), 4.9 (sl, 2H), 2.40 and 2.25 (2s, 3H) ppm., 19064-64-3

As the paragraph descriping shows that 19064-64-3 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; US2011/312934; (2011); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem