Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90766-97-5,5-Bromo-6-phenylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

90766-97-5, To a solution of 5-bromo-6-phenyl-2,3-dihydropyridazin-3-one (0.700 g, 2.788 mmol) in DMF (12 mL), potassium carbonate (0.462 g, 3.345 mmol) was added followed by 2-bromopropane (0.314 mL, 3.345 mmol) and the resulting mixture heated at 60 C. for 2 h. The mixture was partitioned between EtOAc and water, the aqueous phase was extracted with EtOAc, and the combined organic layers were washed several times with brine. The organic phase was dried over sodium sulfate and the solvent was removed. The crude was purified by flash chromatography on silica gel Biotage cartridge (cyclohexane to cyclohexane_EtOAc=85:15) to afford title compound as a pale yellow solid (0.630 g, 2.149 mmol, 77% yield). MS/ESI+ 293.1-295.1 [MH]+, Rt=1.11 min (Method A).

90766-97-5 5-Bromo-6-phenylpyridazin-3(2H)-one 2767911, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; CHIESI FARMACEUTICI S.p.A.; BIAGETTI, Matteo; Capelli, Anna Maria; Guala, Matilde; (42 pag.)US2016/75710; (2016); A1;,
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1120-95-2, 3-Chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The boronate ester (19 g, crude) from Step F above, 3-chloro- pyridazine (4.8 g, 42 mmol), and cesium carbonate (21 g, 63 mmol) were suspended in DMF (120 mL) and water (30 mL). The mixture was purged with argon. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium (240 mg, 0.33 mmol) was added to the mixture. The mixture was heated at 1000C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, and filtered through a pad of Celite. The filtrate was washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (98:1.8:0.2 to 95:4.5:0.5 dichloromethane/methanol/concentrated ammonium hydroxide) to give 5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2, 3,4,5- tetrahydro-lH-benzo[c]azepine (4.7 g, 40% for 2 steps) as an oil. This oil was resolved using Chiralcel OD column (eluente :80 etaep:20 IPA:0.1 DEA) to give (+)- enantiomer (2.3 g, 98%, ([alpha]25D, +26.9 (C, 0.29 Methanol) and (-)-enantiomer (2.3 g, 98%, [alpha]25D, -23.2 (C, 0.28 Methanol)): 1H NMR (CDCl3, 300 MHz) delta 9.15 (d, J= 4.8 Hz, IH), 7.91-7.84 (m, 3H), 7.54-7.50 (m, 2H), 4.96 (t, J= 5.2 Hz, IH), 4.26-4.05 (m, IH), 3.85-3.73 (m, IH), 3.30-3.21 (m, IH), 2.97-2.91 (m, IH), 2.32 (s, 3H) 1.95- 1.85 (m, 2H), 0.91 (s, 9H), 0.097-0.085 (m, 6H); ESI MS m/z 370 [M+H]+.The boronate ester (5.5 g, crude) from Step F above, 3-chloro- pyridazine (2.0 g, ~16 mmol), and cesium carbonate (4.2 g, 13 mmol) were suspended in DMF (30 mL) and water (8 mL). The mixture was purged with argon. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium (400 mg, 0.52 mmol) was added to the mixture. The mixture was heated at 1000C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, and filtered through a pad of celite. The filtrate was washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (98:1.8:0.2 to 95:4.5:0.5 dichloromethane/methanol/concentrated ammonium hydroxide) to give 5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2, 3,4,5- tetrahydro-lH-benzo[c]azepine (1.3 g, 55% for 2 steps) as an brown oil: 1H NMR (CDCl3, 300 MHz) delta 9.15 (d, J= 4.8 Hz, IH), 7.91-7.84 (m, 3H), 7.54-7.50 (m, 2H), 4.96 (t, J= 5.2 Hz, IH), 4.20-4.10 (m, IH), 3.85-3.73 (m, IH), 2.97-2.91 (m, IH), 2.32 (s, 3H) d, J= 7.9 Hz, IH), 7.24 (d, J= 7.9 Hz, IH ), 4.82 (t, J= 4.9 Hz, IH), 3.64-3.61 (m, IH), 3.27-3.18 (m IH), 2.36 (s, 3H), 1.95-1.85 (m, 2H), 1.80-1.63 (m, 2H), 0.91 (s, 9H), 0.097-0.085 (m, 6H); ESI MS m/z 370 [M+H]+., 1120-95-2

The synthetic route of 1120-95-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMR TECHNOLOGY, INC.; BRISTOL-MYERS SQUIBB COMPANY; WO2008/141082; (2008); A1;,
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932-22-9, 4,5-Dichloro-3(2H)-pyridazinone is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,932-22-9

To a solution of 4,5-dichloro-1H-pyridazin-6-one (5 g, 30.31 mmol, 1 eq) in dimethylsulfoxide (100 mL) was added diisopropylethylamin (11.75 g, 90.92 mmol, 3 eq) and tert-butyl piperazine-1-carboxylate hydrochloride (6.75 g, 30.31 mmol, 1 eq). The mixture was stirred at 120 C. for 3 hours. The resulting mixture was cooled to room temperature, filtered and quenched by addition of water (500 mL), then extracted with ethyl acetate (100 mL*3). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure. The residue was purified by silica gel chromatography (dichloromethane: methyl alcohol=200:1 to 100:1). Tert-butyl 4-(5-chloro-6-oxo-1H-pyridazin-4-yl)piperazine-1-carboxylate (8.18 g, 24.95 mmol, 82% yield, 96% purity) was obtained as a yellow solid. LC/MS (ESI) m/z: 315.1 [M+1]+; 1H NMR (400 MHz, CDCl3) delta 11.95 (s, 1H), 7.66 (s, 1H), 3.64-3.57 (m, 4H), 3.44-3.36 (m, 4H), 1.49 (s, 9H).

As the paragraph descriping shows that 932-22-9 is playing an increasingly important role.

Reference£º
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); A1;,
Pyridazine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.933-76-6,4,5-Dichloro-2-methylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.,933-76-6

A mixture of 4,5-dichloro-2-methyl-pyridazin-3-one (551 mg, 3.08 mmol), 3-chloro- lH-indazole (1.17 g, 7.70 mmol), and caesium carbonate (1.48 g, 7.70 mmol) in DMF (15 ml) is heated to 110 C for 1 h. The reaction mixture is cooled then concentrated in vacuo. The reaction mixture is diluted with ethyl acetate (50 ml) and washed with water (50 mL) and brine (50 mL x 2). The organic extract is dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product is purified by chromatography on silica eluting with 0-95% ethyl acetate in isohexane to give the product as a light orange oil (940 mg). 1H NMR (CDC13) delta (ppm) 8.36 (1 H, s) 7.45 – 7.62 (2 H, m) 7.34 (1 H, ddd) 7.08 – 7.20 (3 H, m) 7.04 (1 H, ddd) 6.68 (1 H, d) 3.97 (3 H, s).

As the paragraph descriping shows that 933-76-6 is playing an increasingly important role.

Reference£º
Patent; SYNGENTA LIMITED; BURTON, Paul; KOZAKIEWICZ, Anthony; MORRIS, James Alan; MATHEWS, Christopher John; SHANAHAN, Stephen; WO2013/160126; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1120-95-2, 3-Chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1120-95-2

INTERMEDIATE 306,6-Dimethyl-2-[6-(pyrida2in-3-yloxy)-2,3-dihvdro-4H-l,4-benzoxazin-4-yl]-6,7- dihvdro[ 1 ,3]thiazolor5,4-clpyridin-4(5H)-oneA mixture of Intermediate 17 (53 mg, 0.16 mmol), cesium carbonate (105 mg,0.32 mmol) and 3,6-dichloropyridazine (24 mg, 0.16 mmol) in NMP (2 mL) was heated to 1100C for 12 h. After cooling to r.t. it was concentrated in vacuo. Purification by preparative etaPLC (Method 5) gave the title compound (15 mg, 23%) as an off-white solid. deltaeta (CDCl3) 8.94 (IH, dd, J4.5, 1.3 Hz), 8.02 (IH, d, J2.4 Hz), 7.49 (IH, dd, J8.9,4.5 Hz), 7.19 (IH, dd, J 8.9, 1.3 Hz), 6.89-7.03 (2H, m), 5.21 (IH, s), 4.31-4.39 (2H, m),4.09-4.18 (2H, m), 2.86 (2H, s), 1.37 (6H, s).

The synthetic route of 1120-95-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCB PHARMA S.A.; WO2009/71895; (2009); 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.123696-01-5,5-Methoxypyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.,123696-01-5

0500-1 A mixture of 5-methoxypyridazin-3(2H)-one (2.35 g), phosphoryl bromide (16.0 g), and acetonitrile (90 mL) was stirred for 6 hour under reflux. The reaction mixture was added dropwise to a sodium carbonate aqueous solution under ice-cooling, and ethyl acetate was added thereto. The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate-hexane), thereby obtaining 3,5-dibromopyridazine (1.67 g). MS m/z (M+H): 237.

The synthetic route of 123696-01-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

135034-10-5, 3-Chloro-6-iodopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,135034-10-5

To a suspension of intermediate 4 (3.2g, 13.2mmol) in 1,4-dioxane (40ml) was added 2,3- dichlorophenyl boronic acid (2.5g, 13.2mmol), tris(dibenzyrideneacetone)-di-palladium(0)- chloroform adduct (725mg, 0.79mmol), potassium fluoride (2.5g, 43.5mmol) and tri-tert- butylphosphine-tetra-fluoroborate (458mg, 1.58mmol), the mixture was then heated to 1000C for 1 hour whilst under argon. The dark crude reaction mixture was then evaporated to dryness. The solid was suspended in ethyl acetate (50ml) and poured through cellite and again evaporated to dryness. The sample was then purified by chromatography (9Og of silica) eluting with 10% ethyl acetate/ petroleum ether 40:60. The title compound was obtained as a white solid (2.2g). 1H-NMR (CDCl3) delta 7.38 (IH, t, J= 8), 7.59-7.63 (3H, m), 7.83 (IH, d, J= 9) LC/MS m/z [MH+] 259 consistent with molecular formula Ci0H535Cl3N2

The synthetic route of 135034-10-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2008/116816; (2008); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,141-30-0

22.47 g (150 mmoles) of 3, 6-dichloropyridazine are placed in 50 mL of acetic acid and agitated for 9h under reflux. The reaction medium is diluted in 50 mL of water and concentrated to dryness. The residue obtained is purified by silica gel flash chromatography (CH2Cl2-AcOEt, gradient 100:0 to 50:50 in 45 min) . 16.35 g of white solid are obtained (yield 82%) . TLC silic gel 60 F 254 Merck, CH2Cl2-AcOEt: 50:50, Rf=0.31.

The synthetic route of 141-30-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PIERRE FABRE MEDICAMENT; DUPONT-PASSELAIGUE, Elisabeth; MIALHE, Samuel; RIEU, Jean-Pierre; JUNQUERO, Didier; VALEILLE, Karine; WO2011/15629; (2011); A1;,
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14161-11-6, 3,4,5-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,14161-11-6

A mixture of 3,4,5-trichloropyridazine (0.5 g, 2.73 mmol), 4-(2,5- dimethoxyphenyl)piperidine hydrochloride (0.703 g, 2.73 mmol), and potassium carbonate (0.79 1 g, 5.72 mmol) in dioxane (10 ml) was heated to reflux for 1 h. Themixture was cooled and 35% hydrazine in water (2.469 ml, 27.3 mmol) was added and the mixture was heated to reflux for 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-5-(4-(2,5- dimethoxyphenyl)piperidin- 1 -yl)-3 -hydrazinylpyridazine as a brown oil. (M+H) =364.2.

The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

14161-11-6, 3,4,5-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,14161-11-6

A mixture of 3,4,5-trichloro- pyridazine (200 mg, 0.0011 mol), intermediate 2 (see Example Al/b) (273 mg, 0.0011 mol) and diisopropylamine (0.38 ml, 0.0011 mol) was stirred in 2-propanol (4.0 ml) at 800C for 1 hour. The solvent was evaporated, and the crude mixture was taken back in EtOAc. The organic layer was washed with a saturated solution of sodium bicarbonate and with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 mum) (eluent: EtOAc/cyclohexane 50/50). The pure fractions were collected and the solvent was evaporated, yielding 179 mg (41%) of intermediate 86 and intermediate 87 as a 1/1 mixture of two pyridazine compounds.

The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/32631; (2006); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem