Heterocyclic Building Blocks-Pyridazine

50901-46-7, 1-(Pyridazin-4-yl)ethanone is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50901-46-7

To 1-pyridazin-4-ylethanone (0.230 g) was added 1 , 1-dimethoxy-/V,/V-dimethyl-nnethanannine (0.275 ml_) and the mixture was heated at reflux for 1 hour, cooled to room temperature and allowed to stand overnight. The combined organic layers were concentrated and purified by silica gel chromatography eluting with 0 to 50% acetonitrile in dichloromethane to afford (E)-3-(dimethylamino)-1-pyridazin-4-yl- prop-2-en-1-one as an orange solid. (0933) NMR (400MHz, CDCIs) 9.57 – 9.53 (m, 1 H), 9.32 (dd, 1 H), 7.92 (d, 1 H), 7.84 (dd, 1 H), 5.66 (d, 1 H), 3.24 (s, 3H), 3.00 (s, 3H)

The synthetic route of 50901-46-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SYNGENTA PARTICIPATIONS AG; SCUTT, James, Nicholas; WILLETTS, Nigel, James; SONAWANE, Ravindra; PHADTE, Mangala; KANDUKURI, Sandeep, Reddy; SASMAL, Swarnendu; ARMSTRONG, Sarah; MCGRANAGHAN, Andrea; (155 pag.)WO2019/185875; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

5096-73-1, 6-Chloropyridazine-3-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5096-73-1

2-[6-((1R,2R)-1-Benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-pyridazin-3-yl]-benzoic Acid Ethyl Ester (R1=-OCH2CH3; R41=-CH7CH3) 6-Chloropyridazine-3-carboxylic acid (71 mg, 440 mmol, 1.0 eq.), K2CO3 (185 mg, 1.3 mmol, 3.0 eq.), and 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid ethyl ester (148 mg, 535 mmol, 1.2 eq.) were combined with EtOH (1 mL) and water (0.3 mL). The mixture was stirred, and the reaction vessel was capped, placed under vacuum and purged with nitrogen. SilicaCat DPP-Pd (280 mumol/g loading; 286 mg, 80.2 mmol) was added. The vessel was recapped and microwaved at 100 C. for 20 minutes. The solvent was removed and the product filtered. The pH was adjusted to ~4 with 1N HCl. HATU (136 mg, 356 mmol, 0.8 eq.), DIPEA (233 mL, 3.0 eq.), and (2R,3R)-3-amino-2-hydroxy-4-phenyl-butyric acid ethyl ester (99.5 mg, 446 mmol, 1.0 eq.) were combined in DCM (2 mL) and stirred for 2 hours. AcOH was added and the product was purified by preparative HPLC to yield the title compound as a TFA salt (1.8 mg, 95% purity). MS m/z [M+H]+ calc’d for C26H27N3O6, 478.19. found 478.

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

Reference£º
Patent; THERAVANCE, INC.; US2012/309724; (2012); 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

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