Month: September 2020

1722-10-7, 3-Chloro-6-methoxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 227 To a mixture of4- [3- (methoxymethoxy) propyl]-3- (1-methylethyl)-lH-pyrazole (1.00 g), 3-chloro-6- methoxypyridazine (0.82 g) and N, N-dimethylformamide (15 ml) was added sodium hydride(60%, in oil, 0.24 g) at0 C, and, after termination of hydrogen generation, the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration and washed with water. A mixture of the obtained wet crystals,conc. hydrochloric acid (3 drops) and methanol (15 ml) was refluxed for 4 hours. The reaction mixture was poured into ice water, and the precipitated crystals were collected by filtration, washed with water, dried and subjected to silica gel column chromatography, and 3-{1-[6-methOxypyridazin-3-yl]-3-(1-methylethyl)-lH-pyrazol-4-yl}-1-propanol (300 mg, yield23%) was obtained as a colorless oil from a fraction eluted with acetone-chloroform (1: 4, volume ratio). melting point:122-123 C. 1H-NMR(CDC13) $ : 1.32 (6H, d, J= 6.9Hz), 1.39(1H, t, J= 5.3Hz), 1.84-1. 97 (2H, m), 2.60 (2H, t, J= 7.7Hz), 3.03 (1H, septet, J= 7.0Hz), 3.75 (2H, q, J= 5.8Hz), 4.12 (3H, s), 7.06(1H, d, J= 9.3Hz), 8.11(1H, d, J= 9.3Hz), 8.32(1H, s).

1722-10-7, The synthetic route of 1722-10-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2003/99793; (2003); 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.141-30-0,3,6-Dichloropyridazine,as a common compound, the synthetic route is as follows.

2.70 kg (18.0 mol) of sodium iodide are added in portions at room temperature to a mixture of 5.0 l of water and 11.3 l of 57% aqueous hydroiodic acid (75.2 mol). 2.00 kg (13.4 mol) of 3,6-dichloropyridazine are subsequently added in portions to the solution held at 20 C. The reaction mixture is stirred at 20 C. for 18 hours. 10 l of tert-butyl methyl ether and 4 l of water are added to the reaction mixture. The organic phase is separated off and washed with water and aqueous sodium sulfite solution. The organic phase is concentrated, heptane is added, and the resultant solid is filtered off with suction and washed with heptane. The residue is dried in vacuo: 3-chloro-6-iodopyridazine as colourless leaf-shaped crystals; ESI 241., 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; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/257181; (2011); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

7252-84-8, 3-Amino-6-methoxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7252-84-8, A suspension of tris(dibenzylideneacetone)dipalladium(0) (7.40 mg, 8.09 mumol), 1,1′-bis(dicyclohexylphosphino)ferrocene (9.36 mg, 0.016 mmol), 6-chloro-N-methyl-4-((3-(methylthio)pyridin-2-yl)amino)pyridazine-3-carboxamide (0.1002 g, 0.323 mmol), 6-methoxypyridazin-3-amine (0.081 g, 0.647 mmol) and potassium phosphate tribasic (0.404 ml, 0.809 mmol) in 1,4-dioxane (2.5 mL) in a 1 dram vial underwent a vacuum/N2 cycle three times. The reaction mixture was heated at 80 C. for 3 hours then diluted with water and filtered. The solid was washed with water and dried under vacuum overnight to give crude 6-((6-methoxypyridazin-3-yl)amino)-N-methyl-4-((3-(methylthio)pyridin-2-yl)amino)pyridazine-3-carboxamide (0.119 g, 0.299 mmol, 92% yield). 14 mg of the crude was purified with prep HPLC to give a pure product, 6-((6-methoxypyridazin-3-yl)amino)-N-methyl-4-((3-(methylthio)pyridin-2-yl)amino)pyridazine-3-carboxamide (8.5 mg, 0.021 mmol, 6.40% yield).

The synthetic route of 7252-84-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Chunjian; Yang, Michael G.; Xiao, Zili; Chen, Ling; Moslin, Ryan M.; Tokarski, John S.; Weinstein, David S.; (84 pag.)US2019/152948; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

17973-86-3, 3,6-Dibromopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 26 A mixture of 5 parts of 1-(3-methylphenyl)piperazine dihydrochloride, 10.6 parts of sodium carbonate and 180 parts of N,N-dimethylformamide was stirred for 1 hour at 65 C. Then there were added 7.2 parts of 3,6-dibromopyridazine and the whole was stirred overnight at about 65 C. The reaction mixture was poured into ice water. The product was filtered off and dissolved in dichloromethane. The solution was washed twice with water, dried, filtered and evaporated. The residue was crystallized from ethanol. The product was filtered off and dried, yielding 4.1 parts (61.5%) of 3-bromo-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine; mp. 145.7 C. (compound 136).

17973-86-3, 17973-86-3 3,6-Dibromopyridazine 248852, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Janssen Pharmaceutica N.V.; US5001125; (1991); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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.

[Reference Example 35] 3-Hydrazino-6-methylpyridazine [Show Image] Hydrazine monohydrate (45 mL) was added to a suspension of 3-chloro-6-methylpyridazine (3.00 g) in ethanol (45 mL), and the resultant mixture was heated to reflux for 2.5 hours. After air cooling, a residue obtained by evaporating the solvent of the reaction solution under reduced pressure was purified by silica gel chromatography (chloroform-methanol-water (a lower layer solvent of 7: 3: 1 (v/v)), to obtain the title compound (2.35 g, 81%) as a solid. 1H-NMR(400MHz, DMSO-d6)delta: 2.39(3H, s), 4.20(2H, br), 6.94(1H, d, J=9.3Hz), 7.18(1H, d, J=9.3Hz), 7.64(1H, br). ESI-MSm/z: 125(M+H)+.

1121-79-5, 1121-79-5 3-Chloro-6-methylpyridazine 227254, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1785418; (2007); 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.88491-61-6,3-Bromopyridazine,as a common compound, the synthetic route is as follows.,88491-61-6

To a reaction flask were added compound 5 (200 mg, 0.392 mmol), 3-bromopyridazine (92.9 mg, 0.588 mmol), Pd(dppf)Cl2 (32 mg, 0.02 mmol) and sodium carbonate (126 mg, 1.18 mmol), 2 mL glycol dimethyl ether and 0.4 mL water were added, bubbled with nitrogen gas for 10 minutes, and the reaction was heated to 120 C in microwave and reacted for half an hour. After TLC detected the reaction was complete, the reaction was concentrated, purified by silica gel column chromatography to afford 57 mg of a product, yield: 31.7%. LC-MS(APCI): m/z = 462.1(M+1)+; 1H NMR (400 MHz, DMSO) delta 10.26 (s, 1H), 9.24 (d, J = 3.4 Hz, 1H), 8.84 (d, J = 2.2 Hz, 1H), 8.20 (d, J = 2.2 Hz, 1H), 7.87 (t, J = 7.7 Hz, 3H), 7.80 (dd, J = 8.4, 4.9 Hz, 1H), 7.33 (d, J = 8.8 Hz, 2H), 4.87 (d, J = 3.3 Hz, 1H), 4.20 (s, 1H), 3.44 – 3.36 (m, 1H), 3.17 (d, J = 5.3 Hz, 2H), 2.82 (d, J = 11.2 Hz, 1H), 1.85 (dd, J = 8.6, 4.3 Hz, 1H), 1.74 (s, 1H).

The synthetic route of 88491-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (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.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

Step A 6-(2,4-Dichloro-phenylsulfanyl)-2H-pyridazin-3-one. Potassium t-butoxide (1.1 g) was added to a solution of 2,4-dichlorothiophenol (1.8 g) in N,N-dimethylformamide (DMF) (5 mL). The mixture was stirred at room temperature for 10 minutes and then 6-chloro-2H-pyridazin-3-one (1.31 g) was added. The reaction mixture was stirred at 100 C for five hours. The mixture was then cooled to room temperature, poured into water (20 mL) and 20% potassium hydroxide (5 mL) was added. The resulting dark solution was extracted with ethyl acetate (2X10 mL). The aqueous layer was collected and the pH was adjusted to 3 with concentrated hydrochloric acid. The solutionwas then extracted with ethyl acetate (3X10 mL). The ethyl acetate layer was collected, dried over anhydrous sodium sulfate, filtered and evaporated to obtain a crude product, which was purified by silica gel chromatography (1:1 ethyl acetate/hexane as eluent) to afford 6-(2,4-dichloro-phenylsulfanyl)-2H-pyridazin-3-one (418 mg, 15%); NMR 6.88 (d,1H), 7.10 (d, 1H), 7.24(dd,1H), 7.48 (d,1H), 7.52 (d,1H).

19064-67-6, The synthetic route of 19064-67-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Products Inc.; EP1260224; (2002); 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.34584-69-5,3,6-Dichloro-4,5-dimethylpyridazine,as a common compound, the synthetic route is as follows.

To a stirred solution of 3,6-dichloro-4,5-dimethylpyridazine (500 mg, 2.82 mmol) in carbon tetrachloride (10 mL) was added nu-bromosuccinimide (503 mg, 2.82 mmol), and AIBnu (2.3 mg, 0.014 mmol) in a round bottom flask equipped with condenser. The reaction was continuously irradiated with a 300 W light and refluxed for 5 h. The formed succimide was filtered and the filtrate was concentrated to afford 4-(bromomethyl)-3,6- dichloro-5-methylpyridazine as a brown solid. To a solution of 4-(bromomethyl)-3,6- dichloro-5-methylpyridazine (400 mg, 1.56 mmol) in DMF was added with benzyl amine (188 muL, 1.72 mmol) and TEA (326 muL, 2.34 mmol). The reaction mixture was heated at 90 0C for 2 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to afford a brown oil. The crude material was purified by flash chromatography on silica gel, eluting with 30 – 80percent EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a the title compound as a greasy solid (430 mg, yield: 54percent (two steps)). MS (m/z, MH+): meas. 282.2 calc. 282.05, 34584-69-5

The synthetic route of 34584-69-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

34231-77-1, Methyl pyridazine-4-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 18-crown-6 (0.48 g, 1.8 mM) in tetrahydrofuran (10 mL), there was added a 1.0M potassium tert-butoxide/tetrahydrofuran solution (20 mL, 20 mM) and then the mixture was warmed up to 60 C. Acetonitrile (1.0 mL, 20 mM) was added to the mixture at that temperature, the mixture was stirred for 10 minutes and 4-methoxycarbonyl-pyridazine (2.5 g, 18 mM) was then added thereto. After stirring the mixture at 60 C. for 30 minutes, it was cooled to room temperature, the precipitated solid was recovered through filtration and then washed with tetrahydrofuran. After drying the resulting solid in vacuo, it was suspended in ethanol (50 mL) and then methyl carbazinate (2.3 g, 26 mM) was added thereto. Concentrated hydrochloric acid (1.5 mL) was added to the suspension with ice-cooling and the mixture was stirred at that temperature for 14 hours. The reaction liquid was concentrated under reduced pressure and the excess hydrochloric acid was neutralized by the addition of a saturated sodium bicarbonate aqueous solution. The reaction liquid was extracted with ethyl acetate, the organic phase thus obtained was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to thus give a crude product of the title compound (0.50 g, yield: 13%). MS (ESI) m/z (M+H)+ 220, 34231-77-1

34231-77-1 Methyl pyridazine-4-carboxylate 12439252, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; AJINOMOTO CO., INC.; US2011/294781; (2011); 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.63001-30-9,Methyl 6-oxo-1,6-dihydropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

63001-30-9, To a solution of methyl-6-oxo-l,6-dihydropyridazine-3-carboxylate (5 g, 32.4 mmol) in anhydrous THF (130 mL) was added DHP (8.90 mL, 97 mmol) and catalytic PPTS (1.631 g, 6.49 mmol). The resulting mixture was heated at reflux (75C) for 17 hr. Additional DHP (3.0 mL, 32.4 mmol, 1.0 eq) was added and the mixture was stirred at reflux for an additional 19 hr. The dark solution was cooled and partitioned between ethyl acetate (2 x 150 mL) and water (200 mL). The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica; hexanes/EtOAc 1 :0 to 0: 1 as eluent) to give methyl 6-oxo-l-(tetrahydro-2H-pyran-2- yl)-l,6-dihydropyridazine-3-carboxylate (7.06 g). 1H NMR (CDCI3- J, 500 MHz) delta 7.82 (d, J=9.7 Hz, 1H), 6.96 (s, J=9.7 Hz, 1H), 6.09 (m, 1H), 4.12 (m, 1H), 3.95 (s, 3H), 3.74 (m, 1H), 2.32 (m, 1H), 2.07 (m, 1H), 1.75 (m, 2H), 1.57 (m, 2H)

As the paragraph descriping shows that 63001-30-9 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ARRINGTON, Kenneth, L.; BURGEY, Christopher; GILFILLAN, Robert; HAN, Yongxin; PATEL, Mehul; LI, Chun Sing; LI, Yaozong; LUO, Yunfu; LEI, Zhiyu; XU, Jiayi; WO2014/58747; (2014); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem