Month: October 2020

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.

To a solution of N4 – ((3R, 6S) -6-aminohexahydrofuro [3,2-b] furan-3-yl) -5-chloro-N2- (1-methyl- Yl) pyrimidine-2,4-diamine (32 mg, 0.091 mmol) in n-butanol (20 mL) was added 6-chloropyridazine-3-carbonitrile (25 mg, 0.179 mmol) and triethylamine (42 mg, Mg).The reaction was allowed to warm to 120 C for 20 hours,And then concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (MeOH / DCM (v / v) = 1/30)The title compound was obtained as a yellow solid(17 mg, 0.037 mmol, yield 41%).

35857-89-7, 35857-89-7 6-Chloropyridazine-3-carbonitrile 13382871, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Sunshine Lake Pharma Co., Ltd.; Xi, Ning; Dai, Weilong; Li, Minxiong; Chen, Wuhong; Zhang, Tao; Hu, Haiyang; Li, Xiaobo; Liu, Jun; Wang, Tingjin; (146 pag.)CN106478651; (2017); 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.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

General procedure: A suspension of 3,6-dichloropyridazine (25.50 g, 171.2 mmol) in 100 mL of water was treated with NaOH (15.06 g, 376.6 mmol) and heated at 80 C for 2 h. The resulting red solution was allowed to cool to rt and was then acidified to pH 1 with concentrated HCl (aq). The off-white solid was washed with water and Et2O and then dried under vacuum overnight to afford 6-chloropyridazin-3(2H)-one (4, 19.13 g,85% yield). A mixture of 4 (2.55 g, 19.54 mmol) and EtI (1.88 mL, 23.44 mmol) in 10 mL of DMF at rt was treated with K2CO3 (8.10 g, 58.61 mmol). The reaction mixture stirred 48 h at rt and then H2O was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated to give 6-chloro-2-ethylpyridazin-3(2H)-one (5, 2.70 g, 87% yield). A solution of 5 (2.70 g, 17.03 mmol) in hydrazine hydrate (4.14 mL, 85.13 mmol) was heated at 70 C. After 2 h, the reaction mixture was loaded directly on to a silica gel column and eluted with 0-10% MeOH in CH2Cl2 to afford 2-ethyl-6-hydrazinylpyridazin-3(2H)-one (6, 1.26 g, 48% yield) as a light-yellow solid. A mixture of 6 (163 mg, 1.06 mmol) and 2-chloro-6-fluorobenzaldehyde (168 mg, 1.06 mmol) in 8 mL of EtOH was heated to reflux. After 1 h, the reaction mixture was concentrated, the solid wasresuspended in THF (8 mL) and chloramine T-hydrate (265 mg, 1.16 mmol) was added. The mixture was heated at 65 C for 4 h. The reaction mixture was allowed to cool to rt and H2O was added. The mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford 3-(2-chloro-6-fluorophenyl)-5-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (7, 222 mg, 72% yield). A mixture of 7 (222 mg, 0.76 mmol) and Br2 (0.19 mL, 3.79 mmol) in 3 mL of acetic acid was heated at 80 C for 2 h. The reaction was cooled to rt, water was added and the mixture was extracted with EtOAc. The combined organic layers were washed with H2O and saturated NaHCO3 (aq) and then dried over anhydrous Na2SO4, filtered and concentrated to afford 7,8-dibromo-3-(2-chloro-6-fluorophenyl)-5-ethyl-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (8, 285 mg, 83% yield) as a yellow oil. A solution of 8 (285 mg, 0.63 mmol) in 3 mL of THF at rt was treated with NEt3 (0.26 mL, 1.89 mmol). After 1 h, H2O was added and the mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 7-bromo-3-(2-chloro-6-fluorophenyl)-5-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-6(5H)-one (9, 194 mg, 83% yield) as a yellow oil. In a microwave tube was placed 9 (194 mg, 0.52 mmol), 10 (190 mg, 0.63 mmol), PdCl2(PPh3)2 (18 mg, 0.026 mmol) and 2 M Na2CO3 (aq, 1.3 mL, 2.6 mmol) and 2.5 mL of dioxane. The mixture was heated in a microwave at 120 C for 25 min. After cooling to rt, H2O was added and the mixture was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by HPLC (Phenomenex 150 x 30 mm Luna column) eluting with 5-100% CH3CN in water with 0.1% TFA at 35 mL/min over 15 min to afford 3-(3-(2-chloro-6-fluorophenyl)-5-ethyl-6-oxo-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-7-yl)-N-cyclopropyl-4-methylbenzamide (3j, 69 mg, 28% yield) as an off-white solid.

19064-67-6, 19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various fields.

Reference£º
Article; Herberich, Brad; Jackson, Claire; Wurz, Ryan P.; Pettus, Liping H.; Sherman, Lisa; Liu, Qiurong; Henkle, Bradley; Saris, Christiaan J.M.; Wong, Lu Min; Chmait, Samer; Lee, Matthew R.; Mohr, Christopher; Hsieh, Faye; Tasker, Andrew S.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1226 – 1229;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1837-55-4,3,5-Dichloropyridazine,as a common compound, the synthetic route is as follows.

A solution of 3,5-dichloropyridazine (2.00 g, 13.4mmol), phenylboronic acid (1.64 g, 13.4 mmol), Pd(OAc)2 (0.301 g, 1.34 mmol), 1,2,3,4,5-pentaphenyl-1?-(di-tert-butylphosphino)ferrocene (1.906 g, 2.685 mmol), KF (1.947 g, 33.56mmol), dioxane (50 mL), and water (12 mL) was stirred at reflux for 15 h under N2. The mixturewas diluted with EtOAc, washed with brine, dried over anhydrous Na2SO4, and concentrated to dryness. The residue was purified by flash column chromatography to give the title Compound (1.53 g, 59.8% yield) as white solid. MS (ESI): mass calcd. for C10H7C1N2, 190.63; m/z found, 190.0 [M+Hj., 1837-55-4

The synthetic route of 1837-55-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (528 pag.)WO2017/100662; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a. To 42.1 g 3,6-dichloro pyridazine in acetone 10.5 g of NaI followed by 105 mL HI catalyst (Aldrich 21002-1) was added and left at room temperature for three days, upon workup a quantitative yield of 3,6-diiodopyridazine was obtained.

141-30-0, As the paragraph descriping shows that 141-30-0 is playing an increasingly important role.

Reference£º
Patent; Sterling Winthrop Inc.; US5514679; (1996); A;,
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 L: A dry flask was loaded with the boronate ester (1.27 mmol) from step K above, 3-chloro-6-methylpyridazine (0.24 g, 1.90 mmol), sodium carbonate (0.33 g, 3.17 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (0.08 g, 0.10 mmol). The flask was flushed with argon prior to the addition of N,N-dimethylformamide (16 mL) and water (3.2 mL). The reaction mixture was heated to 120 C. under argon for 1 hour. The cooled reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (3¡Á150 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (first purification 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide; second purification 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford the pyridazinyl benzazepine (150 mg, 34% yield other 4 steps)., 1121-79-5

1121-79-5 3-Chloro-6-methylpyridazine 227254, apyridazine compound, is more and more widely used in various fields.

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

65202-50-8, Methyl 6-chloropyridazine-3-carboxylate is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

65202-50-8, Step B. A solution of ethyl 2-amino-4-(acetylamino)benzoate (4.03 g, 18.13 mmol, Example 4, Step A), p-toluenesulfonic acid, monohydrate (0.5 g, 2.63 mmol) and methyl 6-chloro-3-pyridazinecarboxylate [3.13 g, 18.14 mmol, prepared according to the procedure of Barlin, G. B. and Yap, C. Y. (Aust. J. Chem. 1977, 30, 2319-2322)] in 500 mL of toluene was refluxed under Dean-Stark conditions for 12 h. The mixture was concentrated, dissolved into chloroform, washed with saturated sodium bicarbonate solution, dried (MgSO4), filtered and concentrated. Medium pressure chromatography (silica gel, 5percent methanol in chloroform) afforded methyl 7-acetylamino-10-oxo-10H-pyridazino[6,1-b]-quinazoline-2-carboxylate as a yellow solid, mp 281¡ã-285¡ã C., dec.

As the paragraph descriping shows that 65202-50-8 is playing an increasingly important role.

Reference£º
Patent; Warner Lambert Company; US5340808; (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.144294-43-9,3-Amino-5-methylpyridazine,as a common compound, the synthetic route is as follows.

0396-1 A mixture of 7-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-pyrazol-4-yl)-2-chloro-1,5-naphthyridine (25 mg), 5-methylpyridazine-3-amine (11 mg), tris (dibenzylideneacetone)dipalladium(0) (5 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mg), cesium carbonate (20 mg), and 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 7-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-pyrazol-4-yl)-N-(5-methylpyridazin-3-yl)-1,5-naphthyridine-2-amine (12 mg). 1H-NMR(CDCl3) delta: 8.97 (1H, brs), 8.78 (1H, brs), 8.73 (1H, brs), 8.37 (1H, s), 8.26 (1H, d, J=8.4 Hz), 7.71 (1H, s), 7.44 (1H, d, J=8.4 Hz), 4.84 (2H, s), 3.98 (3H, s), 2.45 (3H, s), 0.87 (9H, s), 0.11 (6H, s). MS m/z (M+H): 462., 144294-43-9

144294-43-9 3-Amino-5-methylpyridazine 14743344, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); 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

General procedure: To a solution of primary amine (0.192 mmol) and triethylamine (0.480 mmol) in tetrahydrofuran (3 mE) at 0 C. were added phenyl chloroformate (0.096 mmol) and the reaction mixture stirred for 60 mm. at RT. The reaction mixture was quenched with water and the phenyl carbamate formed was extracted and the Intermediate 4J (25 mg, 0.096 mmol) in THF was added to the extract and the resulting solution was stirred at room temperature for 2 h. Reaction progress wasmonitored by TLC. The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mE) The combined organic layer was washed with 10% NaHCO3 (2×5 mE), water, dried over Na2SO4 and concentrated to afford crude product as off-white solid. The crude product wasther purified by preparative HPLC.

20744-39-2, 20744-39-2 Pyridazin-4-amine 298492, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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

3-Cyano-6-(4-methylpiperazin-1-yl)pyridazine can be prepared from 6-(4-methylpiperazin-1-yl)-3-iodopyridazine (125 g) and cuprous cyanide (55.26 g) suspended in dimethylformamide (620 cc). 3-Cyano-6-(4-methylpiperazin-1-yl)pyridazine (52.1 g), melting at 149 C, is obtained. 3-Iodo-6-(4-methylpiperazin-1-yl)pyridazine can be obtained from 3,6-diiodopyridazine (158.5 g) and 4-methylpiperazine (120 g) suspended in methanol (1200 cc). 3-Iodo-6-(4-methylpiperazin-1-yl)pyridazine (138.7 g), melting at 149 C, is obtained., 20698-04-8

20698-04-8 3,6-Diiodopyridazine 250383, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Rhone-Poulenc Industries; US4110450; (1978); 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.825633-94-1,5-Iodo-2,3-dihydropyridazin-3-one,as a common compound, the synthetic route is as follows.

5-Iodopyridazin-3 (2H) -one (200 mg, 0.90 mmol) , potassium carbonate (249 mg, 1.80 mmol) , and anhydrous acetonitrile (4.5 mL) were charged to a round-bottom flask equipped with a rubber septum and magnetic stirbar. Methyl iodide (62.0 muL, 0.991 mmol) was charged dropwise via syringe. The flask was then equipped with a reflux condenser and heated at reflux for 1 hour. The reaction mixture was filtered through. The filtrate was evaporated to give the crude product, which was purified by silica gel column chromatography (0-10 MeOH/DCM) to afford 5-iodo-2-methylpyridazin-3 (2H) -one. LC/MS: (M+1) +: 236.80., 825633-94-1

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem