Category: pyridazine

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

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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1046816-38-9, 3-Chloro-6-cyclopropylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The title compound is prepared by reacting N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide and 3-chloro-6-cyclopropyl-pyridazine in the presence of K2CO3 in N-methylpyrrolidinone at 200 C. in a microwave vessel. LC (method 15): tR=1.26 min; Mass spectrum (ESI+): m/z=430 [M+H]+., 1046816-38-9

The synthetic route of 1046816-38-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NOSSE, Bernd; BLUM, Andreas; BREITFELDER, Steffen; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; WELLENZOHN, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/65906; (2013); A1;,
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19064-64-3, 3,6-Dichloro-4-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 24.9 G 3, 6-dichloro-4-methylpyridazine and 56,7 g potassium dichromate in 250 ml of concentrated sulphuric acid are stirred at 40C for 2 h, the reaction mixture is poured onto 1.5 1 ice-water and extracted with ethyl acetate. The organic layer is extracted with water and a saturated solution of NACI, dried over MGS04 and evaporated. The raw product is used without any further purification. Yield : 27.1 G MS: M+1 =193. 1, 19064-64-3

The synthetic route of 19064-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Aventis Pharma Deutschland GMBH; WO2004/46117; (2004); A1;,
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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, The compound (100 mg, 0.631 mmol) obtained in Example 11a was dissolved in methylene chloride (6 mL), triethylamine (0.105 mL, 0.757 mmol) and pivaloyl chloride (78 muL, 0.631 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. A solution of tert-butyl methyl[3-(methylamino)propyl]carbamate (described in J. Med. Chem. 1990, 33, 97-101) (128 mg, 0.631 mmol) in methylene chloride (3 mL) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol = 20:1, v/v) to give a crude Boc compound (202 mg).

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

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2409977; (2012); A1;,
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Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35857-89-7,6-Chloropyridazine-3-carbonitrile,as a common compound, the synthetic route is as follows.

Raw (R)-2-bromo-7-((3,3-dimethylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyrimidine- 6-carboxamide XI (2.05 g, 5.58 mmol) from Step 6 was dissolved in dry dimethylformamide (50 mL) under argon atmosphere. To the solution triethylamine (3.91 mL, 27.9 mmol) and then 6-chloropyridazine-3-carbonitrile (963 mg, 6.69 mmol) were added. Reaction mixture was heated at 80 C with stirring for 1 hour. After cooling to room temperature, 100 mL of water was added and the mixture was extracted with AcOEt (3 x 100 mL). Organic phases were combined, dried and evaporated under reduced pressure. To the residue toluene (50 mL) was added and evaporated under reduced pressure. This was repeated twice. The residue was purified by column chromatography (silica gel, eluent: dichloromethane: methanol = 98:2, v/v). Product was obtained as a light-yellow solid (2.35 g, 4.99 mmol) with the yield of 89%. MS-ESI: (m/z) calculated for C19H21BrN9O [M+H]+= 470.1, found 470.1. 1H NMR (300 MHz, CDCl3 ) delta 11.06 (d, J=8.3 Hz, 1H), 8.44 (s, 1H), 7.50 (d, J=9.7 Hz, 1H), 6.99 (d, J=9.7 Hz, 1H), 6.45 (s, 1H), 6.04 (bs, 2H), 5,49 (dd, J=10.6, 4.2 Hz, 1H), 4.48 (d, 3=133 Hz, 1H), 4,29 (d, J=13.6 Hz, 1H), 3.40 (ddd, J=13.6, 9.4, 3.3 Hz, 1H), 3.17 (d, 3=13 Hz, 1H), 2.26 (dq, 3=113, 3.6 Hz, 1H), 1.96-1.80 (m, 1H), 1.11 (s, 3H), 1.10 (s, 3H).

35857-89-7, The synthetic route of 35857-89-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELON PHARMA S.A.; MROCZKIEWICZ, Michal; STYPIK, Bartosz; BUJAK, Anna; SZYMCZAK, Krzysztof; GUNERKA, Pawel; DUBIEL, Krzysztof; WIECZOREK, Maciej; PIECZYKOLAN, Jerzy; (49 pag.)WO2018/206739; (2018); A1;,
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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

(b) 2-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanol; A solution of ethylene glycol (55 ml) in tetrahydrofuran (200 ml) was treated at around O0C (ice bath cooling) with sodium hydride (60% dispersion in oil, 5.9 g) over 40 minutes. After the addition was complete, 3,4,6-trichloropyridazine (27 g) containing isomers of bromo-dichloropyridazine as impurity was added portionwise and washed in with more dry THF (50ml) and the mixture was stirred at O0C for 1 hour and then at room temperature overnight. The mixture was concentrated (to 1/3 volume) then diluted with aqueous sodium bicarbonate solution and extracted with chloroform (5x) and ethyl acetate (3x). The combined organic extracts were washed with water, dried over sodium sulphate and evaporated and the solids filtered off and washed with CHCI3 (x3) and dried in a vacuum oven overnight at 4O0C affording a white solid (25.5 g, 83%), containing some bromo-derivative (10-15%). MS (+ve ion electrospray) m/z 209/211 (MH+). MS (+ve ion electrospray) m/z 255/7 (MH+), bromo-derivative.

As the paragraph descriping shows that 6082-66-2 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); A1;,
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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

PREPARATION 41 3,5-Dichloro-4-(1-methylethylamino)pyridazine A solution of 3,4,5-trichloropyridazine (9.2 g) and isopropylamine (16.5 g) in toluene (25 ml) is refluxed for 18 hr. Excess isopropylamine is removed by atmospheric distillation. The residual solution is cooled and diluted with dichloromethane and aqueous sodium hydroxide solution (5%). The phases are separated. The organic phase is washed with water and then with saline. The organic phase is dried over sodium sulfate and concentrated under reduced pressure to give a liquid which contains a mixture of isomeric products. The isomers are separated by flash chromatography on silica gel eluding with ether/hexane (30/70). The appropriate fractions are pooled and concentrated to give the desired isomer, NMR (CDCl3) 1.33, 4.59, 4.87 and 8.60delta; CMR (CDCl3) 24.2, 46.4, 117.1,139.3, 145.5 and 151.3 delta. Further elution gives 3,4-dichloro-5-(1-methylethylamino)pyridine which is recrystallized from ether hexane, NMR (CDCl3) 1.35, 3.87, 4.80, and 8.55 delta; CMR (CDCl3) 22.6, 44.7, 116.5, 136.3, 142.5 and 153.4 delta., 14161-11-6

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

Reference£º
Patent; The Upjohn Company; US5599930; (1997); A;,
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Pyridazine | C4H4N2 – PubChem

825633-94-1, 5-Iodo-2,3-dihydropyridazin-3-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

825633-94-1, [00214] Step 4: To a solution of 5-iodopyridazin-3(2H)-one (5 g, 23 mmol) in NJV- dimethylformamide (45 mL, 23 mmol) was sequentially added l-(bromomethyl)-4- methoxybenzene (4.5 g, 23 mmol) and K2C03 (3.4 g, 25 mmol). The mixture was stirred at ambient temperature under N2 atmosphere. After 48 hours, additional 1 -(bromomethyl)-4- methoxybenzene (450 mg, 0.1 equivalent) was added, and the mixture was stirred at ambient temperature for 4 more hours. The mixture was poured into ice water (100 mL) and extracted with EtOAc (3 X 75 mL). The combined organic layers were washed with 2% HC1 followed by brine. The organic layer was dried (MgS04), filtered and concentrated in vacuo. The residue obtained was triturated with EtOAc rhexane to provide the first batch of the product. Mother liquor was concentrated and triturated with CH3CN to provide the second batch of the product. The combined batches gave 5-iodo-2-(4-methoxybenzyl)pyridazin-3(2H)-one (6.2 g, 80% yield) as a solid.

The synthetic route of 825633-94-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); A1;,
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1121-79-5, 3-Chloro-6-methylpyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. To a mechanically stirred solution of 3-chloro-6-methylpyridazine (155.6 mmol) in 140 mL of concentrated sulfuric acid, finely powdered potassium dichromate (55.40 g) was added slowly, the temperature being kept below 50 C. When the addition was complete, stirring was continued for another 4 hours at 50 C. The viscous, dark green liquid was then cooled and crushed ice was added cautiously. The reaction mixture was extracted with ethyl acetate (6*400 mL). The ethyl acetate extracts were combined, dried over anhydrous Na2SO4. The solvent was concentrated in vacuo to yield slightly red colored 6-chloropyridazine-3-carboxylic acid (106.6 mmol). This material was used for next reaction without further purification. Yield 69%. m.p. 145 C. (dec). 1H NMR (300 MHz, DMSO-d6) delta 13.1, 8.20, 8.05., 1121-79-5

As the paragraph descriping shows that 1121-79-5 is playing an increasingly important role.

Reference£º
Patent; XENON PHARMACEUTICALS INC.; US2008/125434; (2008); A1;,
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Pyridazine | C4H4N2 – PubChem