Heterocyclic Building Blocks-Pyridazine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20744-39-2,Pyridazin-4-amine,as a common compound, the synthetic route is as follows.

Compound TDI01249-4 (50 mg, 0.135 mmol), pyridazin-4-amine (15.4 mg, 0.162 mmol), HATU (61.7 mg, 0.162 mmol), DIEA (70 mg, 0.54 mmol) and 4 mL N,N-dimethylformamide were added to a 25 mL single neck flask, and the reaction was performed at room temperature for 0.5 h. LC-MS indicated the reaction was complete. The reaction solution was cooled to room temperature, and added to 20 mL water to give a solid, which was dried and purified by preparative chromatography to afford TDI01249 (14.38 mg, yellow solid, yield: 23.8%). 1H NMR (400 MHz, DMSO-d6) delta 12.89 (s, 1H), 12.33 (s, 1H), 10.94 (s, 1H), 9.62 (d, J = 17.6 Hz, 2H), 9.14 (d, J = 5.8 Hz, 1H), 8.54 (d, J = 5.2 Hz, 1H), 8.36 (d, J = 5.8 Hz, 2H), 8.18 (d, J = 3.2 Hz, 1H), 8.08 (s, 1H), 7.90 (s, 2H), 7.69 (s, 1H), 7.61 (s, 1H), 7.51 (d, J = 8.8 Hz, 1H), 7.38 (d, J = 5.2 Hz, 1H). MS m/z (ESI): 448.0 [M+H].

20744-39-2, The synthetic route of 20744-39-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (106 pag.)EP3421464; (2019); 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.187973-60-0,6-Iodopyridazin-3-amine,as a common compound, the synthetic route is as follows.

General procedure: A 10 mL round-bottomed flask containing a magnetic stirbar was charged with CuI (0.1 mmol) followed by L-hydroxyproline (0.2 mmol),6-iodopyridazin-3-amine (1.3 mmol) and K3PO4 (3.0 mmol). The flask wasflushed with N2 and a solution of the appropriate amine (1.0 mmol) inanhydrous DMSO (1.5 mL) was then added. The mixture was stirred under N2at 50 C for 24 h. MeOH (5 mL) and H2O (5 mL) were added and the stirredmixture was neutralised by dropwise addition of AcOH. The resultant solidswere allowed to settle out and the supernatant solution added to the top of astrong cation exchange (SCX) column. The remaining solid was washed withfurther MeOH (5 mL), and the washings also added to the SCX column. Thesolution was allowed to elute slowly through the column, which was thenflushed with further MeOH. These MeOH washings were discarded. A 1 Msolution of NH3 in MeOH was flushed through until elution of the product wascomplete and the solvent was evaporated under reduced pressure to yield acrude material. Purification was done by flash silica chromatography, elutiongradient typically 0-10% MeOH in CH2Cl2. Relevant fractions were evaporatedto dryness to afford the desired product.

187973-60-0, 187973-60-0 6-Iodopyridazin-3-amine 10867834, apyridazine compound, is more and more widely used in various fields.

Reference£º
Article; Bethel, Paul A.; Roberts, Bryan; Bailey, Andrew; Tetrahedron Letters; vol. 55; 37; (2014); p. 5186 – 5190;,
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

PREPARATION EXAMPLE 1 Preparation of 2-t-butyl-4-chloro-5-[4-(2-isopropylthioethoxy)-benzyloxy]-3(2H)-pyridazinone (Compound No. 310) In 15 ml of N,N-dimethylformamide were dissolved 1.2 g of 2-t-butyl-4,5-dichloro-3(2H)-pyridazinone and 1.2 g of p-(2-isopropylthioethoxy)benzyl alcohol, and then 0.31 g of powdery potassium hydroxide was added thereto. The resulting mixture was stirred overnight at room temperature, poured into water, extracted with diethyl ether, washed with water, dried over anhydrous sodium sulfate and then freed of the diethyl ether by distillation under reduced pressure. The resulting solid was recrystallized from n-hexane to obtain 1.2 g of the aimed compound, m.p. 82.0~84.5 C. 1 H-NMR (CDCl3, delta, TMS): 1.28 (3H, d, J=6.5 Hz), 1.62 (9H, s), 2.90 (2H, t, J=7.0 Hz), 2.90 (1H, dq, J=6.5 Hz), 4.12 (2H, t, J=7.0 Hz), 5.21 (2H, s), 6.85 (2H, d, J=8.4 Hz), 7.29 (2H, d, J=8.4 Hz), 7.69 (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.; US4837217; (1989); 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.66346-87-0,6-Chloro-5-methylpyridazin-3-amine,as a common compound, the synthetic route is as follows.

66346-87-0, Example 65 Preparation of Intermediate 66 [0664] [0665] A mixture of intermediate 58 (293 mg, 0.958 mmol) and 6-chloro-5-methylpyridazin-3-amine (195 mg, 1.35 mmol) in 16 mL of ethanol was heated at 77 C. overnight. After cooling to room temperature the reaction mixture was concentrated under reduced pressure and the residue was purified via silica gel column chromatography (5-100% ethyl acetate in hexanes) to yield intermediate 66 (125 mg, 38%) as a white solid. [0666] LCMS m/z [M+H]+ C17H23ClN4O2 requires: 351.15. Found 351.12. [0667] 1H-NMR (CDCl3, 400 MHz): delta 7.76 (s, 1H), 7.62 (s, 1H), 5.57 (m, 1H), 4.09 (m, 1H), 2.89 (m, 1H), 2.52 (m, 1H), 2.45 (s, 3H), 1.86 (m, 1H), 1.70-1.30 (m, 4H), 1.47 (s, 9H).

66346-87-0 6-Chloro-5-methylpyridazin-3-amine 12353663, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Siegel, Dustin; Sperandio, David; Yang, Hai; Sangi, Michael; Parrish, Jay P.; Hui, Hon Chung; US2013/273037; (2013); A1;,
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Pyridazine | C4H4N2 – PubChem

6082-66-2, 3,4,6-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6082-66-2

1.2. 2-[4-(3,6-dichloropyridazin-4-yl)-piperazin-1-yl]-ethanol In a 50mL round bottom flask, 9.18g (0.05 mol) of 3,4,6-trichloro-pyridazine, 5.30g (0.05 mol) of anhydrous sodium carbonate and 20mL of N,N-dimethylacetamide (DMA) were added, stirred at room temperature, then 6.54g (0.05mol) of 2-(piperazin-1-yl)-ethanol (dissolved in 10ml DMA) was added dropwise slowly, stirred overnight, filtered on the next day. 100mL of distilled water was added into the filter cake and stirred, then filtered again to obtain 10.20g of a white solid, yield: 73.6%, m.p.139~ 141C. 1H-NMR(400MHz, CDCl3) deltappm: 2.57(br, 1H), 2.66~2.68(t, 2H, J=5.12Hz), 2.73~2.76(t, 4H, J=4.76Hz), 3.36~3.38(t, 4H, J=4.52Hz), 3.68~3.71(t, 2H, J=5.04Hz), 6.88(s, 1H). 13C-NMR(400MHz, DMSO-d6) deltappm: 155.14, 149.43, 148.70, 116.64, 60.00, 58.49, 52.44, 48.90. EI-MS m/e: 276.1[M+, 100], 280{[M+4]+, 100}, 245.0, 207.1, 175.1, 100.1, 70.1.

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

Reference£º
Patent; Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China; EP1900735; (2008); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

20698-04-8, 3,6-Diiodopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

I II.5. a 3-lodo-6-phenethyl-pyridazine To 200 ml (100 mmol) 0,5 M phenylethylzincbromid solution in THF are added dropwise a mixture of 26,55 g (80 mmol) 3,6 Diiodopyridazine and 4,622 g (4 mmol) Tetrakis(triphenylphosphine) palladium(O) in 100 ml abs. THF. The reaction mixture is stirred for 3 hours at room temperature. Then the mixture is poured in saturated sodium hydrogencarbonate solution and ethyl acetate is added. The mixture is filtered over Celite and the phases are separated. The organic phase is dried over sodium sulphate. Purification is achieved by chromatography (silica gel, methylene chloride/ ethyl acetate= 19:1 ). Yield: 13,97 g (56 % of theory),Rf value: 0.47 (silica gel, methylene chloride/ethyl acetate= 19:1 )EII mass spectrum: m/z = 31 1 [M+H]+

20698-04-8, The synthetic route of 20698-04-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/71646; (2008); 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

Step H: A round bottomed flask was charged with the triflate (0.20 g, 0.44 mmol) from step G above, bis(pinacolato)diboron (0.12 g, 0.48 mmol) and potassium acetate (0.13 g, 1.33 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (36 mg, 0.04 mmol) in DMF (3 mL). The mixture was refilled with nitrogen three times and then stirred at 80 C. for 1 hour. The mixture was cooled to room temperature. Cesium carbonate (0.43 g, 1.33 mmol), 3-chloro-6-methylpyridazine (0.10 g, 0.67 mmol) and water (2 mL) were added. The mixture was refilled with nitrogen three times and then stirred at 60 C. for 2 hours. After cooling, the mixture was partitioned between methylene chloride and water. The aqueous phase was extracted with methylene chloride. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (10:1 methylene chloride/methanol) to yield the desired benzazepine (70 mg, 46%) as an off-white solid.

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

Reference£º
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

27372-38-9, 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-oxo-1,6-dihydropyridazine-3-carboxylic acid To a solution of 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid (2.50 g, 17.59 mmol) in toluene (44 mL) was added Cu(OAc)2 (450 mg, 2.48 mmol), sodium carbonate (7.01 g, 66.14 mmol) and pyridine (4.4 mL) at room temperature. The resulting solution was stirred for 16 h at 100 C. After the reaction was done, the insoluble solids in the reaction mixture were filtered out and the filtrate was concentrated under reduced pressure to yield 6-oxo-1,6-dihydropyridazine-3-carboxylic acid as a off-white solid (1.80 g, 73%). MS: m/z=177.0 [M+H]+., 27372-38-9

27372-38-9 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid 99621, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

372118-01-9, Methyl 4,6-dichloropyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (20.7 g, 100 mmol),2,4-dimethoxybenzylamine (17.5 g, 105 mmol)And diisopropylethylamine (25.84 g, 200 mmol) were dissolved in acetonitrile (800 mL).After stirring at room temperature for 15 hours,The solvent was removed under reduced pressure, and the residue was dispersed in water (1 L).After stirring for 30 minutes, it was filtered. The filtered solid was washed with water (300 mL) and cold acetonitrile (300 mL) in this order.The target product 6-chloro-4-((2,4-dimethoxybenzyl) amino) pyridazine-3-carboxylic acid methyl ester 31a (26 g, white solid) was obtained,Yield: 76%., 372118-01-9

The synthetic route of 372118-01-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); 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.88497-27-2,3-Amino-6-bromopyridazine,as a common compound, the synthetic route is as follows.

88497-27-2, In a three-neck flask, 3-biphenylboronic acid (5 g, 25 mmol), 3-amino-6-bromopyridazine (4.3 g, 25 mmol), potassium carbonate (6.9 g, 50 mmol), tetrakistriphenylphosphine palladium (0.3) was added. g), tetrahydrofuran (30 mL) and water (15 mL), heating under reflux under nitrogen for 5 hours, extraction with dichloromethane, drying, concentration, purification of the crude product by column chromatography gave the product as 4.6 g, 74% yield.

As the paragraph descriping shows that 88497-27-2 is playing an increasingly important role.

Reference£º
Patent; Shanghai Daoyi Chemical Technology Co., Ltd.; Huang Jinhai; Su Jianhua; (22 pag.)CN107793436; (2018); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem