Heterocyclic Building Blocks-Pyridazine

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 tert-butyl (3R)-3-methylpiperazine-1-carboxylate(500 mg, 2.50 mmol, 1 equiv.) and DIEA(645.3 mg, 4.99 mmol, 2 equiv.) in DMF(5 mL) was added 4,5- dibromo-2,3-dihydropyridazin-3-one (760.6 mg, 3.00 mmol, 1.2 equiv.) in portions at 100 degrees C overnight. The residue product was purified by reverse phase flash with the following conditions: MeCN/H2O(35%-75%,45min) to afford tert-butyl (3R)-4-(5-bromo-6-oxo-1,6- dihydropyridazin-4-yl)-3-methylpiperazine-1-carboxylate(150mg,16.10%) as a yellow oil

5788-58-9 4,5-Dibromopyridazin-3(2H)-one 236181, apyridazine compound, is more and more widely used in various fields.

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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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, Step 1:A solution of carbonyldiimidazole (CDI, 165 ??, 1.0 M in N,N-dimethylformamide, 0.165 mmol) was added to a solution of 3-chloropyridazine-6-carboxylic acid (300 ??,, 0.5 M in N,N-dimethylformamide, 0.15 mmol) in a vial. The mixture was shaken at room temperature for 2 hours. A solution of the relevant amine (300 ??, 0.5 M in N,N-dimethylformamide, 0.15 mmol) was added and the vials shaken at room temperature for 20 hours. The reaction was evaporated to dryness under vacuum. The residue was partitioned between ethyl acetate (2.5 mL) and water (2 mL). The layers were separated and the organic layer was evaporated and the residue used without further purification in the subsequent step.

The synthetic route of 5096-73-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER LIMITED; Gibson, Karl Richard; Owen, Dafydd Rhys; WO2013/61297; (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.286946-24-5,Methyl 3,6-dichloropyridazine-4-carboxylate,as a common compound, the synthetic route is as follows.

Example 71; Preparation of Compound 71; Step A; A solution of 3,6-dichloro pyridazine-4-carboxylic acid methyl ester (2.0 mmol, 0.41 g), diethylisopropyl amine (3.0 mmol, 0.52 mL) and piperazine-1- carboxylic acid te/t-butyl ester (2 mmol, 0.37 g) in dioxane (2 mL) was irradiated using microwave for 20 minutes at a temperature of 80 C. The reaction mixture was concentrated in vacuo, and the resulting residue was purified using flash column chromatography on silica gel (eluent: ethyl acetate) to provide compound 71 A as a yellow solid in quantitative yield. HPLC-MS RT= 1.9 min, mass calculated for formula C15H2ICIN4O4 356.13, observed LCMS m/z 357.1 (M+H).

286946-24-5, 286946-24-5 Methyl 3,6-dichloropyridazine-4-carboxylate 17861811, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; SCHERING CORPORATION; WO2008/54749; (2008); A1;,
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7252-84-8, 3-Amino-6-methoxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(6-Methoxy-pyridazin-3-yl)-methyl-amine : To a solution of 3-AMINO-6- methoxy-pyridazine (90 mg, 0.72 mmol) in THF (2 ml) at 0 C was added sodium hydride (44 mg, 1.08 mmol, 60 % oil dispersion), followed by methyl iodide (0.07 ml, 1.08 mmol). The mixture was stirred at 0 C for 1 h, then allowed to warm to room temperature and stirred for another 2 h. The reaction mixture was diluted with EtOAc (10 ml), washed with saturated NAHC03 aq. , brine, dried over NA2S04, filtered and concentrated by vacuum. The residue was purified by chromatography on silica gel with acetate and hexane (1: 2 to 1: 1) as eluent, yielding 6.0 mg of title compound (6.0 %). H NMR (CDC13) : 6.79 (d, J = 9.0 Hz, 1H), 6.68 (d, J = 10. 5 Hz, 1H), 4.29 (brs, 1H), 4.01 (s, 3H), 3.01 (d, J = 4. 8 Hz, 3H).

7252-84-8, As the paragraph descriping shows that 7252-84-8 is playing an increasingly important role.

Reference£º
Patent; MYRIAD GENETICS, INC.; CYTOVIA, INC.; WO2005/3100; (2005); A2;,
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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

A solution of 6-chloro-pyridazine-3-carboxylic acid methyl ester in NaOMe in [MEOH] [(1M,] [10ML)] was refluxed on. [H20] was added and the mixture was extracted three times with DCM to give organic phase [I.] The combined organic phases I were dried and concentrated to give the title compound (40 mg, 10percent). The water phase was acidified with concentrated hydrochloric acid and extracted three times with DCM to give organic phase II. The combined organic phases II were dried and concentrated to give 6-methoxy-pyridazine-3-carboxylic acid (LC-MS [(M++1)] : 155) (230 mg, 65percent). A solution of 6-methoxy-pyridazine-3-carboxylic acid in thionyl chloride (6 ml) was refluxed for 3 h. The reaction was cooled to ambient temperature and evaporated to dryness. [MEOH] (10 ml) was added to the residue and the solution was stirred on at rt. Saturated [NAHC03] (aq) was added and the mixture was extracted three times with DCM. The combined organic phases were dried and concentrated to give the title compound (253 mg, 100percent). LC-MS [(M++1)] : 169.

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

Reference£º
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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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.

Intermediate 141 ,1 -dimethylethyl 4-(6-chloro-3-pyridazinyl)-1 -piperazinecarboxylate In a microwave vial were mixed: 1 ,1 -dimethylethyl 1 -piperazinecarboxylate(135 mg, 0.725 mmol, available from Fluka), 3,6-dichloropyridazine (90 mg, 0.604 mmol, available from Alfa Aesar) and DIPEA (0.137 mL, 0.785 mmol) in Tert-Butanol (2 mL). The reaction was stirred and heated in an Emrys Optimizer microwave at 100C for 20 mins then for 30 mins at 150C. The reaction mixture was partitioned between EtOAc (20mL) and water (20mL) and the organic layer washed with brine (20mL) before being dried through an hydrophobic frit and concentrated. The residue was dissolved in DCM and purified by SP4 on a 12+M silica cartridge using a gradient of 10-50% EtOAc in cyclohexane. The appropriate fractions were collected and concentrated to yield the desired product as a white solid, 1 ,1 -dimethylethyl 4-(6-chloro-3-pyridazinyl)-1 – piperazinecarboxylate (1 14.2 mg). LCMS (Method C): Rt = 0.85, MH+ = 299

141-30-0, 141-30-0 3,6-Dichloropyridazine 67331, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); 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, DMSOd6) 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).

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

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15456-86-7,4-Bromo-1,2-dihydropyridazine-3,6-dione,as a common compound, the synthetic route is as follows.

c) 3,4,6-Trichloropyridazine; This was prepared by a slight variation on the method of Kasnar et al, Nucleosides & Nucleotides (1994), 13(1-3), 459-79.Hydrazine sulphate salt (51 g) was suspended in water (250 ml), heated to reflux and bromomaleic anhydride (90.38 g) was added dropwise. The mixture was heated at reflux for 4 hours then cooled to room temperature. The reaction was repeated with 29 g hydrazine sulphate, 53 g bromomaleic anhydride and 130 ml water. The precipitates were collected by filtration, washed with water and acetone and dried as a combined batch in vacuo to afford 4-bromo-1,2-dihydro-3,6-pyridazinedione as a white solid (113 g). The solid in two batches was treated with phosphorus oxychloride (2¡Á200 ml) and heated to reflux for 3.5 hours. The mixture was cooled, evaporated and azeotroped with toluene. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution and extracted with DCM twice more. The organic extracts were dried and evaporated. This residue was re-dissolved in dichloromethane, and chromatographed on silica gel (300 g) (DCM as eluent) to give a white solid (101.5 g, 87%).(LC-MS analysis showed ca 20-30% impurity, isomers of bromo-dichloropyridazine).MS (+ve ion electrospray) m/z 184/185/186 (MH+), trichloropyridazine.MS (+ve ion electrospray) m/z 228/229/231 (MH+), bromo-dichloropyridazine.

15456-86-7, As the paragraph descriping shows that 15456-86-7 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; US2010/56502; (2010); A1;,
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90766-97-5,90766-97-5, 5-Bromo-6-phenylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-bromo-6-phenylpyridazin-3(2H)-one (1.522 g, 6.06 mmol) in DMF (90 mL) was added tert-buty 2-(((ls,4s)-4-(tosyloxymethyl)cyclohexyl)methoxy)acetate (2.50 g, 6.06 mmol), potassium 2-methylpropan-2-olate (1.360 g, 12.12 mmol) and 18-crown-6 (0.320 g, 1.212 mmol). The reaction was stirred at 40 0C for 16 h, quenched with water (40 mL), extracted with EtOAc (4 x 50 mL), and washed with brine. The combined organic phases were dried over MgSO4, filtered, and concentrated to give a brown oil. The brown oil was purified by silica gel column chromatography to give the title compound as a yellow oil (1.346 g). LCMS mlz = 491.3 [M+Eta]+; 1H NMR (400 M Hz, CDCl3) delta ppm, 1.37-1.64 (m, 17H), 1.80-1.90 (m, IH), 2.23 (bs, IH), 3.42 (d, J= 7.07 Hz, 2H), 3.94 (s, 2H), 4.17 (d, J = 7.71 Hz, 2H), 7.44-7.49 (m, 4H), 7.50-7.55 (m, 2H).

As the paragraph descriping shows that 90766-97-5 is playing an increasingly important role.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; HAYASHI, Rena; IBARRA, Jason B.; ULLMAN, Brett; ZOU, Ning; WO2010/77275; (2010); A1;,
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141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Hydroiodic acid (250mL) was added to a mixture of 3, 6-dichloropyridazine (149g, 1 mol CAS:[135034-10- 5]) and Nal (180g, 1 .2mol) in 500mL of CHCI3. After the addition, the mixture was stirred at ambient temperature for 24h, and poured into water and extracted with dichloromethane three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give 3- chloro-6-iodopyridazine. H-NMR (400Mz, DMSO-d6) delta: 7.63 (d, 1 H), 8.16 (d, 1 H)., 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; SYNGENTA CROP PROTECTION AG; SYNGENTA (CHINA) INVESTMENT CO., LTD.; EDMUNDS, Andrew; HALL, Roger Graham; MUEHLEBACH, Michel; EMERY, Daniel; JUNG, Pierre Joseph Marcel; LU, Long; WU, Yaming; CHEN, Ruifang; (156 pag.)WO2016/169886; (2016); A1;,
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