Category: 14161-11-6

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

A mixture of 3,4,5-trichloropyridazine (0.250 g, 1.363 mmol), (2,3-dihydro-1H-inden-2-yl)methanamine hydrochloride (0.250 g, 1.363 mmol), and potassiumcarbonate (0.396 g, 2.86 mmol) in dioxane (10 ml) was heated to reflux for 1 h. The mixture was cooled and 35% hydrazine (2.469 ml, 27.3 mmol) was added. The mixture was heated to reflux for 16 h overnight. The reaction was diluted with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over5 magnesium sulfate, and concentrated to give 5-chloro-N-((2,3-dihydro-1H-inden-2- yl)methyl)-6-hydrazinylpyridazin-4-amine. LCMS: Rt = 1.85 mi (M+H7 = 290.1. The material was used without purification.

14161-11-6, As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); 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

A mixture of 3,4,5-trichloropyridazine (0.25 g, 1.363 mmol), 4-(2,3- dichlorophenyl)piperidine, 4-methylbenzenesulfonate salt (0.547 g, 1.3 63 mmol), andpotassium carbonate (0.396 g, 2.86 mmol) in dioxane (5 ml) was heated to reflux for1 h. The mixture was cooled and 35% hydrazine in water (2.469 ml, 27.3 mmol) was added. The mixture was heated to reflux for 16 h. The reaction was diluted with ethyl acetate and water. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated to give 4-chloro-5-(4-(2,3-dichlorophenyl)piperidin- 1 -yl)-3 -hydrazinylpyridazine as a brown oil. (M+H) =374.1.

14161-11-6, The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); 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.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

A solution of 3,4,5-trichloropyridazine (470 mg, 2.56 mmol) in ethanol (30 ml) was cooled to 0C and saturated with ammonia gas and stirred at room temperature for 4 days. The reaction mixture was then purged with nitrogen for 2 h, and filtered to remove ammonium chloride. The filter cake was washed with anhydrous ethanol, the filtrate and washes were used directly in the next step.MS (electrospray): m/z [M+H]+ = 164, 165, 166, 167, 168, 69 4- Pyridazinamine (D11)A solution of 3,5-dichloro-4-pyridazinamine and 5,6-dichloro-4-pyridazinamine (may be prepared as described in Description 0; 419.8 mg, 2.56 mmol), sodium hydroxide (246 mg, 6.14 mmol) and Pd/C (136 mg, 0.128 mmol) in ethanol (20 ml) was hydrogenated overnight. The reaction mixture was purged with nitrogen and filtered. The filtrate was concentrated to a residue and triturated with ethyl acetate. The mixture was filtered again to collect a solid which was dried to yield the title compound as a yellow solid. 98 mg.MS (electrospray): m/z [M+H]+ = 96

14161-11-6, As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); 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.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

To a solution of 3,4,5-trichloropyridazine (880 mg, 4.80 mmol) in EtOH (10 mL) was slowly added a solution of Intermediate I-57 (2 g, 5.76 mmol) and DIPEA (2.5 mL, 14.40 mmol) in EtOH (10mL). The reaction mixture was refluxed for 6h and evaporated. The residue was dissolved in DCM and washed with water. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography (Biotage, DCM/MeOH 100:0 to 80:20) to yield Intermediate 1-58 (1.3 g, 55%) as yellow solid. It was used in later experiments without further purification.1H NMR (300 MHz, CDCI3) delta 8.67 (s, 1H), 7.36 – 7.16 (m, 15H), 3.84 (m, 4H), 3.64 (t, J = 5.4 Hz, 2H), 3.33 (t, J = 5.1 Hz, 2H).

14161-11-6, As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; BLANCO-APARICIO, Carmen; RODRIGUEZ-ARISTEGUI, Sonsoles; GOMEZ DE LA OLIVA, Cristina Ana; HERNANDEZ HIGUERAS, Ana Isabel; GONZALEZ CANTALAPIEDRA, Esther; AJENJO DIEZ, Nuria; WO2013/5057; (2013); 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.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

Preparation 9.1: 5-(4-methylpiperazin-l-yl)pyridazin-4-amine 7o Step 1: 3,4-dichloro-5-(4-methylpiperazin-l-yl)pyridazine [00283] 3,4,5-Trichloropyridazine (3 g, 16.36 mmol) was dissolved in dry NMP (18 mL) and cooled in an ice-bath. DIPEA (2.326 g, 3.135 mL, 18 mmol) was added, followed, dropwise, by 1-methylpiperazine (1.721 g, 1.906 mL, 17.18 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure to give an brown solid whichwas partitioned between 10% MeOH in DCM and saturated NaHC03. The aqueous layer was extracted with further 10% MeOH in DCM (5x20mL) and the combined organics were dried over Na2S04, filtered and concentrated under reduced pressure to give a brown oil which was purified by column chromatography (7.5% MeOH in DCM, ~300mL silica, loaded in DCM) to provide 3,4-dichloro-5-(4-methylpiperazin-l- yl)pyridazine as a light yellow solid (2.36g, 58% Yield)., 14161-11-6

The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BRENCHLEY, Guy; CHARRIER, Jean-damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; JIMENEZ, Juan-miguel; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; SHAW, David; STORCK, Pierre-henri; STUDLEY, John; TWIN, Heather; WO2014/143241; (2014); 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.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

Example 157 4-Isopropylamino-3,5-dichloropyridazine 3,4,5-Trichloropyridazine (9.2 g 0.05 mol) is dissolved in toluene (24 ml). Isopropylamine (16.5 g, 0.28 mol) is added and the mixture refluxed three hrs. The solution is cooled, diluted with chloroform and sodium hydroxide (1N). The organic phase is separated, washed with water and saline, then dried over sodium sulfate, filtered and concentrated. The concentrate is chromatographed (silica gel, 300 g; ethyl acetate/hexane (30/70)) to give the title compound, NMR (300 MHz, CDCl3) 8.50, 4.74, 4.47 and 1.20delta., 14161-11-6

The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pharmacia & Upjohn Company; US5866589; (1999); A;,
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

47.93 g (0.261 mole) of 3,4,5-trichloro-pyridazine are dissolved in ethanol and 49.7 ml (r=0.982 g/cm3, 0.65 mole) of 3-amino-1-propanol are added to it under stirring. The solution is heated to boiling, boiled for 30 minutes and a sample is taken for TLC (eluent: a 10:10:0.5 mixture of ethyl acetate:acetone:triethylamine, Rf values: (XI)=0.90, (IV)=0.48, (IVA)=0.32, contamination of unknown stucture=0.75). The reaction takes place generally within 30 minutes and 1 hour, the whole amount of the starting substance is used up. The reaction mixture is then evaporated, 13 g of sodium chloride are dissolved in distilled water and the thus-obtained solution is added to the evaporated mixture under stirring. The reaction mixture is allowed to stand in a refrigerator overnight at 5 C. The separated crystals are washed with 10 to 12 ml of cold distilled water and the precipitate is dried. Thus 27.7 g (47.7%) of crude product (IVA) are obtained. M.p.: 150-153 C. After recrystallization from methanol the melting point rises to 157-158 C. The physical characteristics will be specified later. [00051] The aqueous mother liquor is extracted 5 times with 200 cm3 each of ethyl acetate, dried over hot magnesium sulfate, filtered on activated carbon and evaporated to dry. The bulk of the residual crude product is the compound of formula (IV). [00052] Yield of the crude product: 28.02 g (48.32%), according to HPLC analysis it contains 7 to 8% of (IVA) and 1 to 2% of contamination of unknown structure. The crude product is purified by recrystallization from cold diethyl ether in the following way: 300 ml of diethyl ether are added to it in 5 portions and the oily product is stirred at room temperature. The ether solution is decanted on every occasion and fresh ether is used. The ether solutions are combined, evaporated to a volume of 100 ml and the separated crystals are filtered off. Thus 15.6 g (26%) of compound of the formula (IV) are obtained. M.p.: 65-66 C. According to MPLC analysis carried out after purification (IVA) <3.0% and (IV)>97%. For the elaboration of the HPLC method small amounts of standards have been prepared by column chromatography. HPLC method: [00053] Column: Ultrasphere SI 3 mm. 75 cm¡Á4.6 mm. [00054] Eluent: cyclohexane:ethyl acetate (1:1). [00055] Flow rate: 1.0 ml/min. [00056] Detection: UV 254 nm. [00057] Injected volume: 20 ml (0.8% dilution). [00058] Retention times: 5.13 for compound (IV) and 13.46 minutes for compound (IVA).The Physico-chemical Characteristics of 4-(3-hydroxypropyl-amino)-3,5-dichloropyridazine (IV) [00059] M.p.: 65-66 C. [00060] TLC: ethyl acetate_triethylamine=20:0.5 [00061] Rf=0.36[TABLE-US-00001] Analysis for the formula C7H9Cl2NO3 (222.08): CHClN Calculated: 37.86%4.09%31.93%18.92% Found: 37.624.12%31.71%18.67% IR (KRr) nu cm-1: 3249, 2947, 1591, 1454, 1390, 1353, 1212, 1177, 1124, 1075, 1037, 908, 683, 522, 460. [00062] 1H-NMR (DMSO): delta 8.70 [s, (1H) pyridazine C-6 ], 6.8 [t, (1H) 4-NH], 4.7 [t, (1H) OH], 3.74 [qa, (2H) N-CH 2], 3.5 [qa, (2H) CH2-O-] 1.73 [m, (2H) C-CH2-C]. [00063] 13CNMR (DMSO) delta ppm: 150.8, 116.0, 140.1, 114.7 (pyridazine carbon atoms), (60 C-OH), (43.6 NH-C), (31.9 C-CH2-C).Physico-chemical Characteristics of the 5-(3-hydroxypropyl-amino)-3.4-dichloropyridazine (IVA) [00064] M.p.: 157-158 C. [00065] TLC: ethyl acetate_triethylamine=20:0.5 [00066] Rf=0.16[TABLE-US-00002] Analysis for the formula C7H9Cl2N3O (222.08): CHClN Calculated: 37.86%4.09%31.93%18.92% Found: 37.684.11%31.77%18.73% IR (KBr) nu cm-1: 3269, 2935, 1568, 1334, 1283, 1224, 1139, 1070, 1043, 861, 830, 795, 661, 540, 514. [00067] 1H-NMR (DMSO): delta ppm: 8.73 [s,(1H) pyridazine C-6], 7.59 [t,(1H) 5-NH], 4.66 [t,(1H) OH], 3.4-3.6 [m,(4H) CH2-X X=heteroatom], 1.73 [m,(2H) C-CH2C]. [00068] The stereoscopic vicinity of the NH proton at position 5 and the pyridazine proton at position 6 has been proved by a DNOE experiment. [00069] 13CNMR (DMSO) delta ppm: 152.1, 143.7, 137.2, 114.4 (pyridazine carbon atoms), (58.4 C-OH), (39.9 C-NH), (31.4 C-CH2-C).

14161-11-6, The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Egis Gyogyszergyar Rt.; US6800758; (2004); B1;,
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,14161-11-6

To a solution of Intermediate I-09 (1.6 g, 8.72 mmol) in CH3CN (50 mL) was added a solution of Intermediate I-04 (2.04 g, 17.44 mmol) in CH3CN (50 mL). The reaction mixture was stirred at rt for 24 h, at 50C for 10 h, and at rt for 2 days. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (Biotage, cHex/EtOAc 80:20 to 0:100) to afford Intermediate 1-13 (1.20 g, 52%).HPLC-MS (method 4): Rt= 3.78 min, [M+H]+ m/z 264.1H NMR (300 MHz, CDCI3) delta 8.78 (s, 1H), 3.52 (s, 2H), 3.26 (s, 2H), 3.23 (s, 3H), 0.85 (s, 6H).

As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); MCNEENEY, Stephen, Phillip; PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; MARTIN HERNANDO, Jose Ignacio; RODRIGUEZ HERGUETA, Antonio; RICO FERREIRA, Maria del Rosario; BLANCO APARICIO, Carmen; WO2013/4984; (2013); 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.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.

General procedure for chlorine substitution for different amines To a solution of 3,4,5-trichloropyridazine (1 eq) in MeOH (1 mL/mmol) was added dropwise a solution of the appropriate aminoalcohol (ex: 2-methylamino-ethanol) (3 eq) in MeOH (1 mL mmol) for 1h at RT. The solvent was removed in vacuo to give a brown oil which was purified by Biotage flash column chromatography (eluent: 70% EtOAc in cyclohexane to 100% EtOAc) to give the desired product (ex: 2-[(5,6-Dichloro-pyridazin-4-yl)-methyl-amino]-ethanol). Example: Synthesis of Intermediate 1-10 -pyridazin-4-yl)-methyl-amino]-ethanol: 1H NMR (300 MHz, CDCI3) delta 8.60 (s, 1H), 3.90 (t, J = 5.4 Hz, 2H), 3.72 (m, 2H), 3.20 (s, 3H).

14161-11-6, As the paragraph descriping shows that 14161-11-6 is playing an increasingly important role.

Reference£º
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; BLANCO-APARICIO, Carmen; RODRIGUEZ-ARISTEGUI, Sonsoles; GOMEZ DE LA OLIVA, Cristina Ana; HERNANDEZ HIGUERAS, Ana Isabel; GONZALEZ CANTALAPIEDRA, Esther; AJENJO DIEZ, Nuria; WO2013/5057; (2013); 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

Step A: 4-Aminopyridazine A solution of 10.1 grams (0.055 mole) of 3,4,5-trichloropyridazine in 100 ml of absolute ethanol, in a 200 ml pressure bottle, was cooled to 0 C. and saturated with ammonia gas. The bottle was sealed and the reaction mixture stirred at ambient temperature for 4 days. The reaction mixture was purged with nitrogen for 2 hours then filtered to remove ammonium chloride. The filter cake was washed with anhydrous ethanol. The filtrate and washed were placed in a Parr hydrogenation bottle and 5.2 grams (0.13 mole) of sodium hydroxide and 0.6 gram of 10% palladium on charcoal were added. The volume of the mixture was brought to 200 ml with absolute ethanol. The mixture was hydrogenated for 4 hours using a Parr hydrogenator, during which time the theoretical amount of hydrogen was taken up. The hydrogenation bottle was purged with nitrogen and the reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to a residue. The residue was dried under reduced pressure at ambient temperature for several hours. The residue was triturated with 250 ml of ethyl acetate, and the mixture allowed to stand for 7 days under anhydrous conditions. The mixture was filtered to collect a solid. The solid was dried under reduced pressure at 40 C. to give 3.9 grams of 4-aminopyridazine. The nmr spectrum was consistent with the proposed structure., 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; FMC Corporation; US4735650; (1988); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem