Category: pyridazine

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

Compound 4-((tetrahydro-2H-thian-4-yl) oxy) aniline 45c (200 mg, 0.955 mmol)And 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (200 mg, 0.97 mmol) in ethanol (10 mL),Heat to 90 C in a sealed tube and stir for 12 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 1/1 to 1/2),The target product 6-chloro-4-((4-((tetrahydro-2H-thian-4-yl) oxy) phenyl) amino) pyridazine-3-carboxylic acid methyl ester 45d (240 mg, yellow solid ),Yield: 66%.

372118-01-9, The synthetic route of 372118-01-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
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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), 4-(3- methoxyphenyl)piperidine (0.26 1 g, 1.363 mmol), and potassium carbonate (0.3 96 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. The mixture was heated to reflux for an additional 16 h. The reaction was diluted with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated to give 4-chloro-3-hydrazinyl- 5-(4-(2-methoxyphenyl)piperidin-1-yl)pyridazine as a brown oil oil that was usedwithout purification. LCMS: Rt = 0.77 mm, 22%, (M+H) = 334.

14161-11-6, 14161-11-6 3,4,5-Trichloropyridazine 70111, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (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.135034-10-5,3-Chloro-6-iodopyridazine,as a common compound, the synthetic route is as follows.

b) Ethyl (?)-3-(3-Chloro-6-pyridazinyl)-2-propenoate.; A suspension of 3- chloro-6-iodopyridazine (2.4 g, 10 mmol), ethyl acrylate (4.4 mL, 40 mmol), palladium(II) acetate (90 mg, 0.40 mmol) and tri(o-tolyl)phosphine (366 mg, 1.20 mmol) in DMF (10 mL) and diisopropylethyl amine (5 mL) was stirred with heating (1 1 1 C oil-bath) for 3.5 h, cooled to room temperature, diluted with H20 (50 mL) and extracted with EtOAc (300 mL). The extract was washed (brine) and dried. After solvent removal at reduced pressure, the residue was chromatographed (14% to 20% EtOAc/hexane) to give 174 mg (8%) of ethyl (E)-3- (3-chloro-6-pyridazinyl)-2-propenoate as a brown solid, mp 106-1 10 C. IR 2928, 1715, 1 186 cm”1; 1H NMR (CDC13) delta 1.38 (t, J= 7.5 Hz, 3H, CH2G?), 4.33 (q, J= 7.5 Hz, 2H, CH2CH3), 7.98 (d, J = 16.2 Hz, 1H, CH=CHCO), 7.57 (d, J= 8.4 Hz, 1H, 4-ArH), 7.63 (d, J = 8.4 Hz, 1H, 5-ArH), 7.86 ppm (d, J= 16.2 Hz, 1H, CH=CHCO). HRMS calcdC9H9C1N202 [M + H]+ 213.0425, found 213.0431., 135034-10-5

As the paragraph descriping shows that 135034-10-5 is playing an increasingly important role.

Reference£º
Patent; WAYNE STATE UNIVERSITY; SANDFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; FONTANA, Joseph, A.; DAWSON, Marcia; XIA, Zebin; WO2011/79305; (2011); 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

A solution of pyridazine (2.2 g, 27.5 mmol) and 2-phenylacetic acid (18.7 g, 137.5 mmol), AgNO3 (1.4 g, 8.25 mmol) in 2N H2SO4 (27.7 ml) was heated to 60-70 C. under stirring, then, a solution of (NH4)2S2O8 (18.6 g, 82.5 mmol) in 80 ml of water was added within 20 minutes, After heating to 70-90 C. for 1.5 hour, the reaction solution was cooled to room temperature and extracted with DCM (2¡Á100 ml), the combined organic layers were washed with 2NH. SO4 (3¡Á70 ml), then, the combined aqueous layer was made alkaline with 50% NaOH and extracted with DCM (3¡Á80 ml), dried over Na2SO4 and concentrated to get the crude product, which was purified by column chromatography on silica gel (petroleum Ether: EtOAc=2:1) to afford 4-benzylpyridazine (1.0 g, yield: 22%). 1H NMR (CDCl3 400 MHz): delta9.09 (s, 1H), 9.06 (d, J=5.2 Hz, 1H), 7.40-7.28 (m, 3H), 7.25-7.20 (m, 1H), 7.18 (d, J=7.2 Hz, 2H), 4.0 (s, 2H), 289-80-5

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

Reference£º
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
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70952-62-4, 3,6-Dichloro-4-methoxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Description 1; 4-(6-Chloro-4-methoxy-pyridazin-3-ylamino)-piperidine-l-carboxylic acid tert- butyl ester (Dl); To a stirred solution of 3,6-dichloro-4-methoxy-pyridazine (0.73 g, 4.08mmol) (prepared by a procedure similar to that described in Eichenberger, K.; Rometsch, R..; Druey, J. Australian Journal of Chemistry 1956, 9, 1755-1764), 4-amino-piperidine-l- carboxylic acid tert-bvXy ester (0.98 g, 4.90 mmol) and cesium carbonate (2.66 g, 8.16 mmol) in toluene (15 ml) in a sealed tube under nitrogen, were added (R)-(+)-2,T- bis(diphenylphosphino)-l,r-binaphthyl (0.38 g, 0.61 mmol) and palladium(II) acetate (0.046 g, 0.20 mmol). The reactiom mixture was stirred at 110 C for 18 h.. After cooling to room temperature, the reaction mixture was filtered though Celite and the filtrate was evaporated. The crude product was purified by flash column chromatography (silica gel; 3 % ammonia in methanol (7M) / dichloromethane). The desired fractions were collected and evaporated in vacuo, to yield Dl (0.44 g, 32 %) as a yellow solid. Ci5H23ClN4O3 requires 342; Found 343 (MH+).

70952-62-4, The synthetic route of 70952-62-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/128995; (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.5096-73-1,6-Chloropyridazine-3-carboxylic acid,as a common compound, the synthetic route is as follows.

5096-73-1, PREPARATION 13 SYNTHESIS OF 6-CHLOROPYRIDAZINE-3-CARBOXYLIC ACID [2-(3-FLUOROPHENYL)ETHYL]AMIDE To a solution of 6-chloropyridazine-3-carboxylic acid (0.31 g, 1.94 mmol) in dichloromethane(15.5 mL) was added diisopropylethylamine (0.73 mL, 4.19 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.28 g, 2.1 mmol) and 1-(3-dimethylamino)propyl-3-ethylcarbodiimide (0.37 mL, 2.1 mmol). The resulting mixture was stirred for 15 minutes, followed by the addition of 3-fluorophenethylamine (0.28 mL, 2.1 mmol). After stirring for 27 hours at ambient temperature, the reaction mixture was diluted with dichloromethane (200 mL), washed with water (4 x 25 mL), dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography eluted with dichloromethane: ethyl acetate (2:1) afforded the product as a white powder (0.205 g). 1H NMR (400 MHz, CDCl3) delta 8.26, 8.12, 7.67, 7.28-7.23, 6.95-6.89, 3.80-3.75, 2.95.

As the paragraph descriping shows that 5096-73-1 is playing an increasingly important role.

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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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.932-22-9,4,5-Dichloro-3(2H)-pyridazinone,as a common compound, the synthetic route is as follows.

Example 30; 4-Chloro-5-(3-cyclobutyl-2,3,4,5-tetrahydro-lH-benzo[d]azepin-7-yloxy)-2-methyl-2H- pyridazin-3-one; General synthesis of Example 30; Step 1.; To a round-bottom flask was added 4,5-dichloro-2H-pyridazin-3-one (10.0 g, 60.6 mmol), potassium carbonate (16.8 g, 121.2 mmol), iodomethane (4.0 mL, 64.3 mmol), and acetonitrile (80 mL). The reaction mixture was heated at reflux for 12 h and was cooled to room temperature. The reaction was filtered and the filtrate was concentrated. The residue was purified by column chromatography (CH2Cl2) to give 8.21 g (76%) of 4,5- dichoro-2-methyl-2H-pyridazin-3-one. 1HNMR (400 MHz, OMSO-d6) 5 8.18 (s, IH), 3.70 (s, 3H) ; MS (m/z) = 179 (M + l)., 932-22-9

The synthetic route of 932-22-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CEPHALON, INC.; WO2009/142732; (2009); A2;,
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84956-71-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.84956-71-8,2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

EXAMPLE 8 Synthesis of 2-tert.-butyl-4-chloro-5-[4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-benzyloxy]-3(2H)-pyridazinone [Compound (3)] 1.16 g of 4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-benzyl alcohol (Example 3) and, 15 minutes later, 0.95 g of 2-tert.-butyl-4,5-dichloro-3(2H)-pyridazinone are added to a suspension of 0.2 g of sodium hydride at 50% in 10 cc of dimethylformamide. The resulting reaction mixture is stirred for 1 hour at room temperature, is diluted with ether, is washed with diluted HCl and brine; the washed solution is thoroughly dehydrated, the solvent is evaporated off and the so obtained raw reaction product is chromatographed on silica gel with 9/1 hexane/ethyl acetate. 1.3 g of pure product is obtained. Melting point 68-69 C.

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; Presidenza del Consiglio dei Ministri-Ufficio del Ministro per il coordinamento delle iniziative per la ricerva Scientifica e Tecnologica; US5169848; (1992); A;,
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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 stirred solution of 3-chloro-6-methylpyridazine (5.0 g, 39.0 mmol) in concentrated H2S04 (20.0 mL) was added K2Cr207 (13.7 g, 46.8 mmol) in portions at 0 C. After addition the mixture was heated to 50 C for 2 h, the mixture was poured into ice. The water layer was extracted with EtOAc six times. The organic phase was dried and concentrated to give 6-chloropyridazine-3-carboxylic acid (2.5 g, 40%). MS (ESI) calcd for C5H3C1N202: 157.99., 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; SIRTRIS PHARMACEUTICALS, INC.; BLUM, Charles, A.; SPRINGER, Stephanie, K.; VU, Chi, B.; WO2013/59589; (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.17973-86-3,3,6-Dibromopyridazine,as a common compound, the synthetic route is as follows.

Example 24 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)-1-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-yl)propan-2-ol (56) To a stirred solution of 3,6-dibromopyridazine (200 mg, 0.84 mmol) and 4-(trifluoromethyl)phenylboronic acid (159.7 mg, 0.84 mmol) in 1,2-dimethoxyethane (DME; 12 mL) was added 1M sodium carbonate (Na2CO3; 1.2 mL, 1.26 mmol) at RT, and the mixture was degassed by purging with argon for 30 min. To the resulting reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4; 29.1 mg, 0.025 mmol), and the mixture was further degassed for 5 min at RT. The reaction mixture was stirred at reflux for 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT, diluted with H2O (50 mL) and extracted with EtOAc (2*50 mL). The combined organic extracts were washed with H2O (40 mL) and brine (40 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography (eluting with 12% EtOAc/hexane) afforded a mixture of mono and bis-coupled products BC (150 mg, 2:1 ratio), which was taken to the next step without separation. (Note: Both compounds eluted at same Rf; all the characteristic protons were seen in the 1H NMR spectrum.) MS (ESI): 303 [M+H]+. To a stirred suspension of copper powder (0.75 g, 11.81 mmol) in DMSO (3 mL) was added ethyl 2-bromo-2,2-difluoroacetate (1.2 g, 5.92 mmol) at RT, and the mixture was stirred for 1 h. A solution of compound BC (0.9 g, mixture) in DMSO (7 mL) was added to the reaction mixture, and stirring was continued for another 18 h at RT. After completion of reaction (by TLC), the reaction mixture was quenched with satd NH4Cl solution (100 mL) and extracted with EtOAc (2¡Á200 mL). The combined organic extracts were washed with H2O (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. Purification by silica gel column chromatography (eluting with 15% EtOAc/hexane) afforded crude BD (0.7 g, as a mixture) which was taken for the next step without separation. (Note: All the characteristic protons were seen in the 1H NMR spectrum.) LC-MS: 347.8 [M+H]+ at 4.99 RT (73.75% purity).

17973-86-3, As the paragraph descriping shows that 17973-86-3 is playing an increasingly important role.

Reference£º
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
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