Heterocyclic Building Blocks-Pyridazine

37444-46-5, Pyridazin-3-ylmethanol is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 77 -(2-Methoxyphenyl)-7-(4-(pyridazin-3-ylmethoxy)pyrimidin-5-yl)benzo[d]isoxazole[00282] To a stirring solution of pyridazin-3-ylmethanol (0.014 g, 0.124 mmol) in THF (Volume: 0.5 mL) at room temperature was added sodium hydride (4.97 mg, 0.124 mmol). After 5 minutes, Preparation 73C (0.014 g, 0.041 mmol) was added and the reaction mixture was heated at 50 C overnight. The reaction mixture was diluted with 10 drops of water and concentrated. The resulting residue was dissolved in DMF, filtered, and purified via preparative LC/MS with the following conditions: Column: Waters XBridge CI 8, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 methanohwater with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanohwater with 10-mM ammonium acetate; Gradient: 25-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (1.1 mg, 6%). ESI MS (M+H)+ = 412.0. HPLC Peak tr = 2.12 minutes. Purity = 93%. HPLC Conditions: B. XH NMR (400 MHz, MeOD) delta ppm 9.08 (1 hr, dd, J=4.95, 1.65 Hz), 8.81 (1 hr, s), 8.78 (1 hr, s), 7.73-7.80 (2 hr, m), 7.57-7.66 (2 hr, m), 7.41-7.49 (1 hr, m), 7.16 (1 hr, d, J=8.14 Hz), 7.12 (1 hr, td, J=7.54, 0.99 Hz), 5.88 (1 hr, s), 3.87 (2 hr, s).

37444-46-5 Pyridazin-3-ylmethanol 2794575, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Pyridazine – Wikipedia
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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

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

Reference£º
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/257181; (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.932-22-9,4,5-Dichloro-3(2H)-pyridazinone,as a common compound, the synthetic route is as follows.

To a suspension of 4,5-dichloro-2-hydroxypyradizine (5.00 g, 30.3 mmol) in methanol (90 mL) at room temperature, sodium methoxide (30% in methanol, 32.8 mL, 182 mmol) was added. The mixture was heated to reflux for 2 days then was concentrated to dryness. The residue was dissolved in water and acidified with glacial acetic acid. The white precipitate that formed was collected by filtration, washing with water. The solid was dried under vacuum to give 4-chloro-5-methoxypyridazin-3(2H)-one (29-1, 2.99 g).

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

Reference£º
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); 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.6082-66-2,3,4,6-Trichloropyridazine,as a common compound, the synthetic route is as follows.

Step 1: 4,6-dichloropyridazin-3(2H)-one and 5,6-dichloropyridazin-3(2H)-one A solution of 3,4,6-trichloropyridazine (20.0 g, 109.04 mmol) in HOAc (100 mL) was heated at 100 C for 12 h, at which time TLC indicated the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (petroleum ether : Ethyl acetate = 1 : 1 ) to give the title compounds (11.2 g, 63% yield) (1 : 1 ratio of regioisomers) as a white solid. LCMS M/Z (M+H) 165. Step 2: 4,6-dichloro-2-methylpyridazin-3-(2H)-one and 5,6-dichloro-2-methylpyridazin-3-(2H)-one To a suspension of 4,6-dichloropyridazin-3(2H)-one and 5,6-dichloropyridazin-3(2H)-one (11.2 g, 67.89 mmol), and Cs2CO3 (33.2 g, 101.83 mmol) in DMF (100 mL) was added CH3I (10.6 g, (0355) 74.68 mmol). The resulting mixture was stirred at 25 C for 15 h, at which time TLC indicated the reaction had gone to completion. The reaction mixture was quenched by addition of a saturated aqueous solution of ammonium chloride (100 mL), and then extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether : ethyl acetate = 1 : 1 ) to give the title compounds (7.5 g, 62% yield) (1 : 1 ratio of regioisomers) as white solids. LCMS M/Z (M+H) 179. Step 3: 4-amino-6-chloro-2-methylpyridazin-3-(2H)-one A mixture of 4,6-dichloro-2-methylpyridazin-3(2H)-one (7.5 g, 41.90 mmol, mixture with 5,6- dichloro-2-methylpyridazin-3(2H)-one) in ammonium hydroxide (48%, 50 mL) was heated at 120 C for 15 h in a sealed tube, at which time LCMS indicated that the reaction had gone to completion. After cooled, the product was collected by filtration. The crude solid was washed with water and dried under reduced pressure to give a mixture of two regioisomers (3.8 g, 57%, 1 : 1 ratio) as white solids. LCMS M/Z (M+H) 160. Step 4: 4-amino-6-chloro-5-iodo-2-methylpyridazin-3-(2H)-one To a solution of 4-amino-6-chloro-2-methylpyridazin-3(2H)-one (3.8 g, 23.81 mmol, mixture with regio- isomers) in acetonitrile (60 mL) was added l -iodopyrrolidine-2,5-dione (5.4 g, 23.81 mmol). The reaction mixture was heated to reflux for 3 h, at which time LCMS indicated that the reaction had gone to completion. After cooled, the reaction was quenched by addition of a saturated aqueous solution of ammonium chloride (20 mL), and then extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether : ethyl acetate = 1 :3) to give a mixture of regioisomers with a 1 : 1 ratio (2.5 g, 37% yield) as yellow solids. LCMS M/Z (M+H) 286.

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

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven; NASVESCHUK, Christopher, G.; PASTOR, Richard; ROMERO, F. Anthony; TAYLOR, Alexander, M.; (179 pag.)WO2016/36954; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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 N4-((3R,65)-6-aminohexahydrofuro[3,2-*]furan-3-yl)-5-chloro-N2-(l- methyl-lH-pyrazol-4-yl)pyrimidine-2,4-diamine (32 mg, 0.091 mmol) in butan-l-ol (20 mL) were added 6-chloropyridazine-3-carbonitrile (25 mg, 0.179 mmol) and triethylamine (42 mg, 0.415 mg). The reaction was stirred at 120 C for 20 hours and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/30) to give the title compound as a yellow solid (17 mg, 0.037mmol, yield 41%). LC-MS (ESI, pos. ion) m/z: 455.4 [M+H]+;1H NMR (400 MHz, CDCh) delta (ppm): 7.81 (s, 1H), 7.55 (s, 1H), 7.48 (s, 1H), 7.40 (d, J = 9.1 Hz, 1H), 6.78 (d, J = 9.3 Hz, 1H), 4.71 (s, 1H), 4.64-4.57 (m, 3H), 4.24-4.14 (m, 2H), 4.00-3.96 (m, 1H), 3.81 (s, 3H), 3.69-3.66 (m, 3H).

The synthetic route of 35857-89-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; DAI, Weilong; XI, Ning; LI, Minxiong; ZHANG, Tao; LI, Xiaobo; HU, Haiyang; CHEN, Wuhong; WANG, Tingjin; LIU, Jun; (188 pag.)WO2017/48675; (2017); 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.17973-86-3,3,6-Dibromopyridazine,as a common compound, the synthetic route is as follows.

EXAMPLE 27 A mixture of 4.1 parts of 3,6-dibromopyridazine, 4.34 parts of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]piperazine, 6.4 parts of sodium carbonate and 188 parts of N,N-dimethylformamide was stirred overnight at 65 C. The reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1.1 parts (16.4%) of 3-bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine; mp. 169.1 C. (comp. 75).

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

Reference£º
Patent; Janssen Pharmaceutica N.V.; US4992433; (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.1837-55-4,3,5-Dichloropyridazine,as a common compound, the synthetic route is as follows.

A solution of 3,5-dichloropyridazine (2.00 g, 13.4 mmol), phenylboronic acid (1.64 g, 13.4 mmol), Pd(OAc)2 (0.301 g, 1.34 mmol), 1,2,3,4,5-pentaphenyl- 1?-(di-tert-butylphosphino)ferrocene (1.906 g, 2.685 mmol), KF (1.947 g, 33.56 mmol), dioxane(50 mL), and water (12 mL) was stirred at reflux for 15 h under N2. The mixture was diluted with EtOAc, washed with brine, dried over anhydrous Na2504, and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound (1.53 g, 59.8% yield) as white solid. MS (ESI): mass calcd. for C10H7C1N2, 190.63; m/z found, 190.0 [M+H].

As the paragraph descriping shows that 1837-55-4 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (524 pag.)WO2018/103060; (2018); 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.289-80-5,Pyridazine,as a common compound, the synthetic route is as follows.

50 mL of ammonia was condensed in a 200 mL, 3-NECK flask equipped with dry ice condenser. After the addition of a crystal of Fe (N03) 3, potassium (468 mg, 12.0 mmol) was added in small pieces AT-78 C. The cooling bath was removed and the intense dark blue mixture was brought to a gentle reflux until a light grey slurry was obtained. After cooling TO-78 C, 0.35 mL (4.80 mmol) of pyridazine was added and the mixture was stirred for 10 minutes. Solid KM : NO4 (2. 65 g, 16. 8 mmol) was added in small portions, the cooling bath was removed, and the mixture was stirred for 10 minutes The reaction was carefully quenched with 1.2 g of solid ammonium chloride. 20 mL of methanol was added and the ammonia was left to evaporate in the hood. The black mixture was filtered through CELIEZ filter aid, the filtrate was concentrated in vacuo, and the resulting black solid was purified on SI02 (100% CH2CL2 to 10% MeOH in CH2C12, gradient) to yield pyridazin-4-ylamine as a brownish solid (380 mg; 83% yield). Bromination of pyridazin-4-ylamine was performed in the same manner as for the preparation of 4-amino-3-bromo-2,6-dimethylpyridine. Chromatography on Si02 (20% ethyl acetate in hexanes to 100% ethyl acetate, gradient, followed by 2% methanol in ethyl acetate) yielded 4- amino-3-bromopyridazine (first eluting: 15% yield) and 4-amino-5-bromopyridazine (second eluting: 5% yield) as tan solids.

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Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/30213; (2005); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 14 6-Chloro-3-chloromethylpyridazine A suspension of 3-chloro-6-methylpyridazine (3 g), benzoyl peroxide (150 mg) and N-chlorosuccinimide (3.12 g) in CCl4 (30 ml) was refluxed 16 hours, cooled, filtered and evaporated. Chromatography (EtOAc/hexane) gave title compound (1.67 g). NMR delta (CDCl3) 4.87 (2H, s), 7.58 (1H, d), 7.71 (1H, d).

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

Reference£º
Patent; Aitken, Steven; Brooks, Gerald; Dabbs, Steven; Frydrych, Colin Henry; Howard, Steven; Hunt, Eric; US2004/58937; (2004); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem