Heterocyclic Building Blocks-Pyridazine

88497-27-2, 3-Amino-6-bromopyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To ie/f-butyl 3-(4,4 5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1 ]-oct-2-ene-8- carboxylate (1 .93 g, 5.75 mmol) and 6-bromopyridazin-3-amine (1 .00 g, 5.75 mmol) in 1 ,4- dioxane (25 mL) is added 2M aq. Na2C03 solution (11 .5 mL, 23.0 mmol) and Xphos 2nd generation catalyst (136 mg, 0.17 mmol). The reaction mixture is degassed with argon and stirred at 100C for 2 h. All volatiles are evaporated under reduced pressure. The crude material is purified by normal phase chromatography to obtain the title compound. (0913) Yield: 0.80 g (46%) ESI-MS: m/z = 303 (M+H)+, 88497-27-2

The synthetic route of 88497-27-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; SMITH KEENAN, Lana Louise; LOWE, Michael D.; RAZAVI, Hossein; SARKO, Christopher Ronald; SURPRENANT, Simon; TAKAHASHI, Hidenori; TURNER, Michael Robert; WU, Xinyuan; (182 pag.)WO2019/81637; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

20744-39-2, Pyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

20744-39-2, To a microwave reaction tube were added 12c (250 mg, 0.273 mmol), pyridazin-4-amine (39.0 mg, 0.410 mmol), DIPEA (0.191 mL, 1.093 mmol), HATU (125 mg, 0.328 mmol) and DMF (15 mL). The mixture was heated to 100 C for 2 hrs under microwave. The mixture was cooled to room temperature and purified by MADP (acidic mobile phase) to give the title compound (30.5 mg, 0.079 mmol, 28.9 % yield) as a yellow solid. LCMS: 375.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 10.72 (s, 1H), 9.19 (br., 1H), 9.05 (d, J= 5.6 Hz, 1H), 8.01 (d, J= 3.6 Hz, 1H), 7.48 (d, J= 6.8 Hz, 2H), 7.34 (d, J= 6.8 Hz, 3H), 7.19 (d, J= 8.8 Hz, 1H), 6.85 (br., 1H), 6.75 (d, J= 8.8 Hz, 1H), 5.15 (s, 2H), 3.22 (br., 4H), 1.96 (br., 4H). 13C NMR (101 MHz, CDCl3): delta 165.1, 151.5, 147.9, 143.7, 143.6, 137.6, 135.3, 129.6, 129.3, 128.8, 120.7, 117.1, 114.9, 114.1, 114.0, 73.1, 48.1, 25.5. HRMS (ESI): m/z calcd for C22H22N4O2 [M+H]+ 375.1821, found [M+H]+ 375.1816.

As the paragraph descriping shows that 20744-39-2 is playing an increasingly important role.

Reference£º
Article; Ding, Xiao; Stasi, Luigi Piero; Dai, Xuedong; Long, Kai; Peng, Cheng; Zhao, Baowei; Wang, Hailong; Sun, Changhui; Hu, Huan; Wan, Zehong; Jandu, Karamjit S.; Philps, Oliver J.; Chen, Yan; Wang, Lizhen; Liu, Qian; Edge, Colin; Li, Yi; Dong, Kelly; Guan, Xiaoming; Tattersall, F. David; Reith, Alastair D.; Ren, Feng; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 212 – 215;,
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.1722-10-7,3-Chloro-6-methoxypyridazine,as a common compound, the synthetic route is as follows.

A solution of 2,2,6,6-tetramethylpiperidine (12.9 ml, 76.1 mmol) in THF (100 mL) was sparged with N2(g) then cooled to -78 C. The -78 C solution was treated slowly with 2.5 M n-butyllithium in hexane (30.4 mL, 76.1 mmol) then warmed to 0 C and stirred for 1 h. The resulting reaction mixture was cooled to -78 C then treated with a 0.46 M solution of 3-Chloro-6-methoxypyridazine in THF (75 mL, 34.6 mmol). After stirring at -78 C for 1 h, the reaction mixture was treated with iodomethane (4.74 mL, 76.1 mmol), and stirred for an additional 30 mm at -78 C. The reaction mixture was quenched with saturated NH4C1(aq) (50 mL), warmed to ambient temperature, diluted with water (50 mL) and extracted with EtOAc (2 x 250 mL). The combined organic extracts were washed with brine (1 x 50 mL), dried over anhydrous Na2SO4(), filtered and concentrated under vacuum to afford the title compound (3.31 g, 60% yield). MS (apci) m/z = 159.0 (M+H).

1722-10-7, 1722-10-7 3-Chloro-6-methoxypyridazine 74403, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; COOK, Adam; GUNAWARDANA, Indrani W.; HUNT, Kevin W.; METCALF, Andrew T.; MORENO, David; REN, Li; TANG, Tony P.; (263 pag.)WO2017/70708; (2017); 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.17973-86-3,3,6-Dibromopyridazine,as a common compound, the synthetic route is as follows.

Step 1: 3,6-Dibromopyridazine (500 mg, 2.1 mmol), 4-(3-methoxy-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazole (970 mg, 2.52 mmol), Pd(dppf)Ci2 (77 mg, 0.11 mmol), K2CO3 (870 mg, 6.3 mmol) were mixed in a Schlenk tube. The reaction was degassed with N2 for 15 min and dioxane (8 mL) and water (1 mL) were added and the reaction was heated to 90 C for 16 h. The reaction was cooled to room temperature, partitioned between EtOAc and water. The organic layers were dried over Na2S04, concentrated under vacuum, purified via column chromatography: eluting with gradient hexanes/EtOAc (0% to 40% EtOAc), column: silica 4 g, to provide 3-bromo-6-(2-methoxy-4-(l-(tetrahydro-2H-pyran- 2-yl)-lH-pyrazol-4-yl)phenyl)pyridazine (690 mg, 79%) as an off-white fluffy solid .

17973-86-3, As the paragraph descriping shows that 17973-86-3 is playing an increasingly important role.

Reference£º
Patent; PTC THERAPEUTICS, INC.; BABU, Suresh; BHATTACHARYYA, Anuradha; HWANG, Seongwoo; JANI, Minakshi; MOON, Young-choon; SYDORENKO, Nadiya; (214 pag.)WO2017/100726; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

54709-94-3,54709-94-3, 5-Methylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 13B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid To a stirred solution of the subtitle compound of Step 13A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for a further 10 min at 60 C., the viscous green mixture was poured on crushed ice. The solids were filtered off and washed with cold water. After drying in vacuo the subtitle compound was isolated (4.5 g, 77%). 1H NMR (400 MHz, (CD3)2SO): delta 7.22 (s, 3H), 8.13 (s,1H), 13.38 (s, broad, 1H).

The synthetic route of 54709-94-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GRANBERG, Kenneth; Holm, Bjorn; Nagard, Mats; US2009/111825; (2009); 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

Example 139; N-[9-(3-Fluoro-benzyl)-6-(6-methyl-pyridazin-3-yl)-2,3,4,9-tetrahydro-lH- carbazol-3-yl]-isobutyramideDissolve N-[9-(3-flourobenzyl)-6-(4,4,5,5-tetramethyl[l ,3,2]dioxaborolan-2- yl)-2,3,4,9-tetrahydro-lH-carbazol-3-yl]isobutyramide (Preparation 23) (150 mg, 0.31 mmol) and 3-chloro-6-methylpyridazine (39 mg, 0.31 mmol) in dioxane (2.5 mL) and 2M Na2Ctheta3 (388 muL). Sparge the solution with nitrogen for 5 min, add dichlorobis(triphenylphosphine)palladium (S) (11 mg, 0.016 mmol) and seal the reaction vessel. Heat to 140 0C in a microwave reactor for 30 min, then dilute with water (20 mL). Extract into EtOAc (3 x 25 mL), dry organics (MgSO4), filter, and concentrate in-vacuo to give the crude product (179 mg) as a brown solid. Purify the crude product on silica gel (12 g), eluting with 25-70% (4% (2M NH3/Me0H)/CH2Cl2)/hexanes to afford 35 mg (25%) of the title compound as a white solid. MS (ES): m/z 457 (M+l), 455 (M-I); HPLC (Method B) Rt = 3.37 min (100%).

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

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
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.7252-84-8,3-Amino-6-methoxypyridazine,as a common compound, the synthetic route is as follows.,7252-84-8

c) 2-ri-(4-fluorophenyl)-3-r2-(4-methoxyphenyl)ethyll-2,5-dioxoimidazolidin- 4-yl1-N-(6-methoxypyridazin-3-yl)acetamide (example 71) TBTU (380.8 mg; 1.16 mmol; 1.5 eq) and DIPEA (270 mu 1-55 mmol; 2 eq) were added to a suspension of 2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-2,5- dioxoimidazolidin-4-yl] acetic acid (I- 10) (300 mg; 0.78 mmol; 1 eq) in dioxane (4 mL). The reaction mixture was stirred at room temperature for 20 minutes. Then, 6- methoxypyridazin-3-amine (145.9 mg; 1.16 mmol; 1.2 eq) in dimethylformamide (0.2 mL) was added and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated to dryness. Saturated ammonium chloride (80 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 80 mL). The combined organic layers were washed with saturated sodium chloride (3 x 80 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound, 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl]-2,5-dioxoimidazolidin-4-yl]-N-(6-methoxypyridazin-3- yl)acetamide, was obtained in 45% yield (173.8 mg) as a white solid. 1H-NMR (DMSO-d6): delta (ppm) 2.8 (m, 2H), 3.09 (m, 1H), 3.28 (m, 1H), 3.7 (s, 4H), 3.98 (s, 3H), 4.54 (t, 1H, J = 4.1 Hz), 6.84 (d, 2H, J = 8.7 Hz), 7.26 (m, 8H), 8.17 (dt, 1H, J = 9.5 Hz, 1.4Hz), 11.18 (s, 1H); MS (ESI+): m/z = 493.9 [M+H]+ .

The synthetic route of 7252-84-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); 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.372118-01-9,Methyl 4,6-dichloropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

Compound 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (600 mg, 2.90 mmol),2,6-difluorophenylboronic acid (1.37 g, 8.70 mmol),Diisopropylethylamine (3g, 23.2mmol), [1,1?-bis (diphenylphosphine) ferrocene] palladium dichloromethane complex (118mg, 0.145mmol)Mixed with 1,4-dioxane (15mL),After deoxygenation, it was heated to 110 C in a microwave reactor under a nitrogen atmosphere and stirred for 1 hour.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 100/0 to 17/3),The target product 4-chloro-6- (2,6-difluorophenyl) pyridazine-3-carboxylic acid methyl ester 67a (223 mg, white solid) was obtained in a yield of 27%., 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

54709-94-3, 5-Methylpyridazin-3(2H)-one is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 10B: 6-Oxo-1,6-dihydropyridazine-4-carboxylic acid; To a stirred solution of the subtitle compound of Step 10A (4.4 g, 40 mmol) in concentrated sulphuric acid (80 mL), potassium dichromate (18 g, 61 mmol) was added in small quantities at 50-60 C. as a finely ground powder. The starting material was added to the mixture within 20 min. Stirring was continued for 10 min at 60 C., the viscous green mixture was poured on crushed ice. The solids were filtered off and washed with cold water. After drying in vacuo the subtitle compound was isolated (4.5 g, 77%).1H NMR (400 MHz, DMSO-d6): delta 7.22 (s, 3H), 8.13 (s, 1H), 13.38 (s, broad, 1H)., 54709-94-3

54709-94-3 5-Methylpyridazin-3(2H)-one 327041, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; AstraZeneca AB; US2009/111821; (2009); 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.50681-25-9,4-Pyridazinecarboxylic Acid,as a common compound, the synthetic route is as follows.,50681-25-9

Preparation 3: methyl 4-pyridazinecarboxylic acid; To a solution of 4-pyridazinecarboxylic acid (490 mg, 3.9 mmol) in MeOH/DCM (20/10 ml) was added at 0 0C trimethylsilildiazomethane (25.5 mmol). The solution was warm at r.t. and stirred overnight. Volatiles were evaporated in vacuo, the crude dissolved in DCM, washed with NaHCO3 satured and dried over Na2SO4. After filtration and concentration to dryness in vacuo, the crude was purified by column chromatography (DCM:MeOH=98 to2) to give 400 mg of the title compound.NMR (1H, CDCI3): delta 9.65 (s, 1 H)1 9.4 (d, 1 H), 7.98 (d, 1 H)1 4.0 (s, 3H). MS (mlz): 139[MH]+.

50681-25-9 4-Pyridazinecarboxylic Acid 2761046, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/108701; (2006); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem