Month: August 2020

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

A) N-(4-acetyl-2-hydroxyphenyl)-6-chloropyridazine-3-carboxamide (1206) To a mixture of 756 6-chloropyridazine-3-carboxylic acid (5 g), 21 DMF (0.122 ml) and 38 THF (70 ml) was added dropwise 145 oxalyl chloride (4.14 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. To the obtained residue were added THF (70 ml), 146 1-(4-amino-3-hydroxyphenyl)ethanone (4.77 g) and 121 triethylamine (13.19 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, and the obtained solid was washed with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue was added 614 diisopropyl ether, and the obtained solid was collected by filtration to give the 949 title compound (2.47 g). 1H NMR (300 MHz, DMSO-d6) delta 2.53 (3H, s), 7.51 (1H, s), 7.55-7.63 (1H, m), 8.21 (1H, d, J = 8.9 Hz), 8.43 (2H, dd, J = 14.8, 8.6 Hz), 10.54 (1H, brs), 10.80-11.07 (1H, m).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; MIZOJIRI, Ryo; BANNO, Hiroshi; ASANO, Moriteru; TOMITA, Daisuke; NII, Noriyuki; MAEZAKI, Hironobu; TAWADA, Michiko; (182 pag.)EP3225618; (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.5096-73-1,6-Chloropyridazine-3-carboxylic acid,as a common compound, the synthetic route is as follows.,5096-73-1

B. To a solution of 6-chloropyridazine-3-carboxylic acid (15.8 mmol) in dichloromethane (95 mL) was added diisopropylethylamine (46.7 mmol), 1-hydroxybenzotriazole monohydrate (23.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (23.7 mmol) under nitrogen atmosphere at ambient temperature. The resulting mixture was stirred for 15 minutes and 2-cyclopropylethylamine (20.2 mmol) was added. After stirring for 36 hours at ambient temperature, the reaction mixture was diluted with dichloromethane (100 mL), then washed with water and dried over anhydrous Na2SO4. The solvent was removed in vacuo. Purification via column chromatography (30% ethyl acetate in hexanes) afforded the title compound (8.70 mmol). Yield 55%.

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

Reference£º
Patent; XENON PHARMACEUTICALS INC.; US2008/125434; (2008); 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.5469-70-5,3-Aminopyridazine,as a common compound, the synthetic route is as follows.,5469-70-5

To a solution of phenyl carbonochloridate (1.070 g, 6.83 mmol), pyridine (0.665 g, 8.41 mmol) in dichloromethane (10 ml) stirred under nitrogen at 25C was added a suspension of pyridazin-3 -amine (0.5 g, 5.26 mmol) in dichloromethane (5ml) during 5 min. The reaction mixture was stirred at 25 C for 1 hr. Next, the organic phase was washed with water 3 mL, saturated brine 3 mL, dried over sodium sulfate and concentrated in vacuo to give the crude product as a white solid. The compound was washed with hexane, dried under reduced pressure, LCMS (m/z) 216.2 (M+H)+.

The synthetic route of 5469-70-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); 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.,6082-66-2

(a) 2-[(3,6-Chloro-4-pyridazinyl)thio]ethanol; A solution of 3,4,6-trichloropyridazine (25 g) in tetrahydrofuran (200 ml) and triethylamine (19 ml) was treated at 00C (ice bath cooling) with 2- mercaptoethanol (8.33 ml) over 5 minutes. After the addition was complete, the mixture was stirred at room temperature for 72 hours. The mixture was stirred with aqueous sodium bicarbonate solution and dichloromethane and the solid was collected, washed with water, ether and pentane and dried in vacuo, giving (22.9 g). The combined aqueous and organic fraction was evaporated to half volume giving further solid, which was washed and dried as above (5.0 g). The total yield of solid (27.9 g; 91 %) contained some bromo-analogue (5-10%) by NMR.

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/115947; (2007); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

66346-87-0, 6-Chloro-5-methylpyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,66346-87-0

EXAMPLE 36 Sodium hydride (60% dispersion in oil; 0.25 g) was added to a solution of 3-amino-6-chloro-5-methylpyridazine (0.36 g) in dry 1,2-dimethoxyethane (10 ml). When evolution of gas ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.67 g) was added and the reaction mixture was stirred for 45 minutes. 7% aqueous citric acid solution (10 ml) was added, the organic phase was separated and the aqueous layer was extracted with ethyl acetate (2*20 ml). The combined organic phases were washed with water (10 ml) and dried (MgSO4). Volatile material was removed by evaporation to give a gum which was triturated first with dichloromethane and then ether to give 5-dimethylamino-N-(6-chloro-5-methyl-3-pyridazinyl)-1-naphthalenesulphonamide (0.2 g), m.p. 110-112 C.; 1 H NMR (d6 -DMSO): 2.30 (s,3H), 2.8 (s,6H), 7.23 (d,1H), 7.52-7.7 (m,3H), 8.3-8.5 (m,3H); mass spectrum (+ve FAB, methanol/dichloromethane/NBA): 376 (M)+.

The synthetic route of 66346-87-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zeneca Limited; US5861401; (1999); A;,
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 solution of 3-amino-6-methoxypyridazine (1.25 g, 10.0 mmol; CASNo. 7252-84-8) in a mix of 1 :1 THF:MeCN (20 ml_), and pyridine (0.83 g, 1.5 mmol) was treated dropwise with phenylchloroformate (1.65 g, 10.5 mmol) in THF (10 mL). After stirring for 3 h, the resulting solid was collected and dried to provide the title compound (2 g, 81 %).

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

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); 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

To the solution of Acid SM-IX (70 mg, 0.20 mmol, 100 mol-%) in dry DMF (2 ml) under nitrogen atmosphere was added i-hydroxybenzotriazole hydrate (HOBt) (60 mg, 0.45 mmol, 220 mol-%), i-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDCI) (86 mg, 0.45 mmol, 220 mol-%) and 3- amino-6-methoxypyridazine (51 mg, 0.41 mmol, 200 mol-%). The reaction mix-ture was stirred at + 50 C for 3.5 hours. Water (3 ml) was added to the reaction mixture. The solid precipitate was filtered and washed several times with water and finally with heptane to yield 56 mg of crude product. Purification was done by flash chromatography. Amount of product compound 3 was 36 mg.1H-NMR (200 MHz, DMSO-d6): 0.98 (5, 3H), 1.20-2.47 (m, 16H),2.60-2.97 (m, 2H), 3.98 (5, 3H), 6.89-7.06 (m, 1H), 7.08-7.21 (m, 2H), 7.25 (d,1H), 8.26 (d, 1H), 10.94 (brs, 1H).

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

Reference£º
Patent; FORENDO PHARMA LTD; HIRVELAe, Leena; HAKOLA, Marjo; LINNANEN, Tero; KOSKIMIES, Pasi; STJERNSCHANTZ, Camilla; (182 pag.)WO2018/224736; (2018); A2;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

84956-71-8, 2-(tert-Butyl)-4,5-dichloropyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,84956-71-8

REFERENCE EXAMPLE 1 Synthesis of 2-tert.-butyl-5-chloro-4-methyl-3(2H)-pyridazinone (starting material) To a solution of 6.0 g (0.25 mol) of magnesium in 50 ml of dry tetrahydrofuran was added dropwise 35.5 g (0.25 mol) of methyl iodide under stream of nitrogen to produce a Grignard reagent. After completion of adding the methyl iodide, 1000 ml of dry toluene was added thereto. The resulting solution was heated to 60 to 70 C. and added dropwise with methyl iodide until the magnesium was completely consumed. The resulting Grignard reagent was cooled to room temperature and was added dropwise over 20 minutes with 22.1 g (0.1 mol) of 2-tert.-butyl-4,5-dichloro-3(2H)-pyridazinone dissolved in 200 ml of dry toluene. After completion of adding, the reaction liquid was subjected to reaction for 1.5 hours at room temperature and then poured into a solution of 100 ml of conc. hydrochloric acid in 900 ml of ice-water to effect extraction. The resulting organic layer was then washed with 500 ml of 10% aqueous solution of sodium hydroxide and then with 500 ml of water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 17.2 g of a crude product. The crude product was subjected to distillation (boiling point: 60 to 62 C./0.22 mmHg) and then column chromatography (silica gel; hexane_acetone=15:1) for separation and purification to give 4.5 g of 2-tert.-butyl-5-chloro-4-methyl-3(2H)-pyridazinone. ND20 =1.5238. NMR (CDCl3, delta, TMS): 1.63 (9H, s), 2.23 (3H, s), 7.66 (1H, s).

The synthetic route of 84956-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nissan Chemical Industries, Ltd.; US4874861; (1989); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

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

Synthesis of 4.5-dichloro-2-(2-(trifluoromethoxy benzvf)pyridazin-3(2HVone (G2-2 To a solution of compound 4 (200 mg, 1.21 mmol), compound 25 (371 mg, 1.45 mmol) and ‘( ‘()’< (335 mg, 2.42 mmol) in DMF (3 mL) was added KI (20 mg, 0.12 mmol). The solution was stirred at 90 C for 2h. The mixture was cooled to room temperature and quenched with water, extracted with EtOAc for 3 times, combined the organic layer, washed with brine, dried over Na_S04, filtered, concentrated under reduced pressure, purified by HPLC to give G2-2 (220 mg, 54%) as a white solid. NMR (DMSO-ife, 300 MHz): delta 5.36 (s, 2H), 7.36-7.41 (m, 3H), 7.44-7.51 (m, IH), 8.25 (s, IH); LCMS [mobile phase: 30-95% Acetonitrile +0.02% NH40Ac] purity is >95%, Rt = 3.989 min; MS Calcd.: 339; MS Found: 340 (M+l)+.

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

Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; BECKWITH, Jonathan Roger; DUTTON, Rachel; ESER, Markus; LANDETA, Cristina; BLAZYK, Jessica L.; MEEHAN, Brian M.; HATAHET, Feras; BOYD, Dana; WO2015/143164; (2015); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem