Heterocyclic Building Blocks-Pyridazine

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

823-58-5, 4-Amino-3,6-dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 112.2: 6-chloro-3-hydrazinylpyridazin-4-amine To a stirred suspension of 3,6-dichloropyridazin-4-amine (Step 112.1) (1.49 g, 9.09 mmol) in EtOH (15 mL) was added hydrazine hydrate (11.04 mL, 227 mmol) and the resulting mixture was heated up and stirred at 100 C. for 3 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was triturated with water (25 mL) to afford the title product (478 mg, 3 mmol, 33% yield) as yellow solid. tR: 0.24 min (LC-MS 2); ESI-MS: 160 [M+H]+ (LC-MS 2); ESI-MS: 158 [M-H]- (LC-MS 2).

As the paragraph descriping shows that 823-58-5 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; US2014/349990; (2014); 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

To a solution of 3,4,5-trichloropyridazine (1 eq) in eOH (1 mUmmol) was added dropwise a solution of the appropiate aminoalcohol (ex: 2-methylamino-ethanol) (3 eq) in MeOH (1 mUmmol)(acetonitrile can be also used). The reaction mixture was stirred at room temperature from 1 h to 2 days depending on the amine. The solvent was removed under vacuum to give a brown oil which was purified by biotage flash column chromatography (70% EtOAc in cyclohexane to 100% EtOAc) to give the desired product (ex: 2-[(5,6-dichloro-pyridazin-4-yl)-methyl- amino]-ethanol).The appropiate dichloropyridazine (ex: 2-[(5,6-dichloro-pyridazin-4-yl)-methyl- amino]-ethanol) (1 eq) was dissolved in THF (20 mL/mmol). When the solution started refluxing, potassium tert-butoxide (1.2 eq) was added portionwise. The reaction mixture was refluxed for 2 h. On cooling, a saturated aqueous solution of amonium chloride was added and the layers were separated. The aqueous phase was extracted with EtOAc (x2). The combined organic layers were dried (sodium sulphate), filtered and evaporated. The residue was triturated with Et20-DCM 9: 1 and filtered off to afford the desired product (ex: 8-chloro-4-methyl-3,4-dihydro- 2H-pyridazino[4,5-b]-1 ,4-oxazine).Intermediate 98-Chloro-4-methyl-3,4-dihydro-2H-p ,5-b]-1 ,4-oxazine:HPLC- S (method 4): Rt =0.98 min, [ +H]* 186.1.1H NMR (300 MHz, CDCI3) delta 8.47 (s, 1 H), 4.42 (m, 2H), 3.46 (m, 2H), 3.06 (s, 3H).Yield: 77% for two steps

14161-11-6 3,4,5-Trichloropyridazine 70111, apyridazine compound, is more and more widely used in various.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); GARCIA COLLAZO, Ana Maria; PASTOR FERNANDEZ, Joaquin; BLANCO APARICIO, Carmen; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco Javier; HERNANDEZ HIGUERAS, Ana Isabel; SALUSTE, Carl-Gustave Pierre; GONZALEZ CANTALAPIEDRA, Esther; MARTINEZ GONZALEZ, Sonia; SALGADO SERRANO, Antonio; NOYA MARINO, Beatriz; WO2011/80510; (2011); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1837-55-4, 3,5-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

At room temperature, was added to the digestion tank 25mL of 3,5-dichloro pyridazine (1.20g, 8.1mmol), and aqueous methylamine (10 mL), which seal; 150 22h is reacted in an oil bath, cooled to room temperature, the reaction solution direct concentrated and the residue was subjected to column chromatography (eluent: CH2Cl2/ MeOH (v / v) = 6/1), to give 1.1g pale yellow solid, yield: 98%

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

Reference£º
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Huang, Jiuzhong; Ren, Xingye; Li, Zhi; Zhang, Yingjun; Zhang, Changchun; (55 pag.)CN105566321; (2016); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

41933-33-9, 2-Benzyl-4,5-dichloropyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 1 Synthesis of 2-benzyl-5-hydroxy-3(2H)-pyridazinone To the mixture of 60 g of 2-benzyl-4,5-dichloro-3(2H)-pyridazinone and 38.8 g of potassium hydroxide was added 250 ml of ethanol and 150 ml of water and heated in an oil bath to the refluxing temperature for 10 hours. After reaction the solvent was distilled off under reduced pressure, and to the residual solution was added 200 ml of water and washed twice with chloroform, the water layer was acidified with concentrated hydrochloric acid. The white solid thus separated was filtered off, washed with water and dried to obtain 55 g of 2-benzyl-4-chloro-5-hydroxy-3(2H)-pyridazinone. Subsequently, in aqueous sodium hydroxide solution (NaOH 1.82 g, water 20 ml) were added 5.0 g of 2-benzyl-4-chloro-5-hydroxy-3(2H)-pyridazinone and 200 mg of 5 % Pd/C, then 474 ml of hydrogen gas was absorbed in the solution under normal pressure. After reaction, Pd/C was filtered off and to the solution was added concentrated hydrochloric acid to be acidified. The white solid thus separated was filtered off, washed with water and dried to obtain 4.1 g of 2-benzyl-5-hydroxy-3(2H)-pyridazinone. melting point: 48-55 C.

The synthetic route of 41933-33-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nissan Chemical Industries, Ltd.; US5278163; (1994); 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.93319-65-4,Pyridazin-3-ylmethanamine,as a common compound, the synthetic route is as follows.

The title compound is prepared according to General Procedure 13 described in Example 52, using 3-{[8-(1-methyl-1 -/-indol-6-yl)quinoxalin-6- yl]amino}pyridine-4-carboxylic acid (Intermediate 42, 80 mg; 0.20 mmol; 1 eq.), pyridazin-3-yl-methylamine (28 mg; 0.25 mmol; 1.25 eq.), EDC-HCI (69 mg; 0.35 mmol; 1.80 eq.), HOBt hydrate (55 mg; 0.35 mmol; 1.80 eq.), triethylamine (0.13 ml0.98 mmol; 5 eq.) and dioxane (5 ml_). Conditions: room temperature for 24 h. Purification by FCC (0% to 10% MeOH gradient in DCM) yields 3-{[8-(1-methyl- H-indol-6-yl)quinoxalin-6-yl]amino}-//- [(pyridazin-3-yl)methyl]pyridine-4-carboxamide (40 mg; 0.08 mmol; 41 %; yellow powder; HPLC purity: 97%).

The synthetic route of 93319-65-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (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.1121-79-5,3-Chloro-6-methylpyridazine,as a common compound, the synthetic route is as follows.

Add trichloroisocyanuric acid (0.189 g) to a solution of 3-chloro-6-methylpyridazine (0.208 g) in chloroform (10 mL). Heat the oil bath to 60 C, lasts for 12 hours. Cool to room temperature, the filtrate was collected by filtration. Concentrated and purified by column chromatography (PE/EA=10/1). 0.201 g of 3-chloro-6-(chloromethyl)pyridazine was obtained.

The synthetic route of 1121-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BetaEpsilonTauTauAlpha PHARMACEUTICALS CO., LTD; WANG, YIQIAN; WANG, JIABING; DING, LIEMING; (80 pag.)TW2018/29406; (2018); 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

A solution of 4,5-dichloropyridazin-3(2H)-one (10 g, 60.6 mmol) in tetrahydrofuran (60 mL, 1.0M) was treated with pyridinium para-toluene sulfonate (3.03 g, 12.1 mmol) and 3,4-dihydro-2H-pyran (8.5 mL, 93.2 mmol). The reaction was heated at reflux for 5 h and was then treated with a second aliquot of 3,4-dihydro-2H-pyran (5.5 mL, 60.3 mmol). The reaction was stirred at reflux overnight. After this time, the reaction was concentrated in vacuo, taken up in ethyl acetate (250 mL), and washed with a 2N aqueous sodium hydroxide solution (2¡Á250 mL). The organics were then washed with a saturated aqueous sodium chloride solution (250 mL), dried over magnesium sulfate, filtered, rinsed, and concentrated in vacuo. Silica gel column chromatography (Biotage, 330 g, 10% ethyl acetate/hexanes) afforded 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (13.01 g, 86%) as an off-white solid; ES+-HRMS m/e calcd for C9H10N2O2Cl2 [M+Na+] 271.0011, found 271.0012.

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

Reference£º
Patent; Berthel, Steven Joseph; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264434; (2009); 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 5-chl oro-Af4-(3 -ethyl pi peri di n-4-yl )-Af4-m ethyl -Af2-(3 – methylimidazo[l,2-a]pyridin-7-yl)pyrimidine-2, 4-diamine (100 mg, 0.250 mmol) and 6- chloropyridazine-3-carbonitrile (53 mg, 0.380 mmol) in ethanol (20 mL) was added TEA (78 mg, 0.771 mmol). The mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by preparative TLC (MeOH/DCM (v/v) = 1/20) to afford the title compound as a yellow solid (86 mg, yield 68%).MS (ESI, pos. ion) m/z: 503.4 [M+H]+;1H NMR (400 MHz, DMSO-d6) d (ppm): 9.91 (s, 1H), 8.29-8.23 (m, 2H), 8.15 (s, 1H), 7.84 (d, J = 9.7 Hz, 1H), 7.41 (d, j= 9.8 Hz, 1H), 7.35 (s, 1H), 7.28 (s, 1H), 4.71 (d, j= 26.9 Hz, 2H), 4.44 (s, 1H), 3.26 (s, 2H), 2.97 (s, 3H), 2.42 (s, 3H), 1.98 (d, j = 11.6 Hz, 1H), 1.93 – 1.74 (m, 2H), 1.43 (s, 1H), 1.06 (s, 1H), 0.87 (t, j= 7.2 Hz, 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; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem