Category: phthalazine

4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, cas is 763111-47-3, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,763111-47-3

General procedure: Intermediates 8 (1 eq) and respective 9-chloroacridine derivatives 4a-4f (1.1 eq) were added to a round flask, and then excessphenol was added as solvent. The reaction system was warmed up to 60 C until phenol was melted and stirred for 0.5 h under argonprotection. Then the mixture was warmed up to 120 C and continued to reaction for more 2 h. After the reaction was completed, themixture was added to ethyl ether drop by drop [2]. The precipitate was filtered and washed twice with new ethyl ether to give pureproducts 9a-9f, which were then characterized by 1H NMR, 13C NMR, melting point and high resolution mass spectrum (HRMS, ESI).

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Reference£º
Article; Dai, Qiuzi; Chen, Jiwei; Gao, Chunmei; Sun, Qinsheng; Yuan, Zigao; Jiang, Yuyang; Chinese Chemical Letters; vol. 31; 2; (2020); p. 404 – 408;,
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75884-70-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.75884-70-7,6-Bromophthalazin-1(2H)-one,as a common compound, the synthetic route is as follows.

To a stirred solution of commercially available 2a (100mg, 0.444 mmol) in DMF was added NaH (32 mg, 1.333 mmol) at 0 oC. After stirring for 20 min, 3-methoxybenzyl bromide (62 muL, 0.444 mmol) was added into the cooled solution. Then the reaction was transferred to RT and kept stirring for 12h. The reaction mixture was concentrated to dryness under vacuum and then partitioned between CH2Cl2 and water. The organic layer was washed with brine and dried over MgSO4. The organic phase was concentrated to dryness under vacuum and puried via a ash chromatography silica gel plate (20 ¡Á 20 cm) to afford intermediate 3a (petroleum ether/ethyl acetate, 2/1) in 45% yield as a pale yellow solid. 1H NMR (400 MHz, DMSO) delta 8.42 (s, 1H), 8.26 (d, J = 1.8 Hz, 1H), 8.18 (d, J = 8.5 Hz, 1H), 8.03 (dd, J = 8.5, 1.9 Hz, 1H), 7.24 (t, J = 7.8 Hz, 1H), 6.87 (s, 2H), 6.85 (dd, J = 7.7, 2.9 Hz, 1H), 5.28 (s, 2H), 3.72 (s, 3H).

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Article; Miao, Zhuang; Sun, Yu-meng; Zhao, Lan-ying; Li, Yue-shan; Wang, Yi-fei; Nan, Jin-shan; Qiao, Ze-en; Li, Lin-li; Yang, Sheng-yong; Bioorganic and Medicinal Chemistry Letters; vol. 30; 6; (2020);,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one, cas is 1242156-59-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,1242156-59-7

2-(4-Bromo-2-fluoro-benzyl)-6-tert-butyl-8-fluoro-2H-phthalazin-1-one To a 20 mL reaction vial with stirbar was added 6-(tert-butyl)-8-fluorophthalazin-1(2h)-one (200.00 mg; 0.91 mmol; 1.00 eq.), 4-bromo-2-fluorobenzyl bromide (267.63 mg; 1.00 mmol; 1.10 eq.), and cesium carbonate (591.75 mg; 1.82 mmol; 2.00 eq.) in ACN (6.00 ml; 114.88 mmol; 126.50 eq.). The reaction vial was sealed and heated to 80 C. overnight. Concentrated and purified by flash chromatography (KP-sil column, 10 g; 5-50% EtOAc/hexanes 15 CV). Concentrated product fractions and dried to afford 218 mg (59%) of the title compound as a orange solid. HPLC: 97% purity. MS: 408 [M+H]+

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Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, cas is 763111-47-3, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,763111-47-3

A reaction mixture of amine precursor (51 mg, 0.139 mmol), 4-carboxylphenylboronic acid pinacol ester (38 mg, 0.153 mmol), HATU (60 mg, 0.158 mmol) and DIPEA (50 muL) in DMF (1 mL) was stirred at room temperature overnight. Water (10 mL) was added, and precipitate was filtered and rinsed with water, and then dissolved in ethyl acetate. After drying by magnesium sulfate, the solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford final product (37 mg) as white solid. M.P.: 288-291 C; 1H NMR (400MHz, CDCl3) delta 10.66 (s, 1H), 8.47 (s, 1H), 7.85-7.72 (m, 5H), 7.38-7.33 (m, 4H), 7.04 (m, 1H), 4.29 (s, 2H), 3.73 (m, 4H), 3.37 (m, 4H), 1.35 (s, 9H), 1.27 (s, 3H). 13C NMR (100MHz, CDCl3) delta 160.4, 145.5, 142.2, 135.0, 134.4, 133.7, 131.6, 129.5, 129.2, 128.3, 127.2, 126.1, 125.0, 121.5, 84.1, 37.7, 29.7, 24.8; HRMS m/z: calcd for C33H34BFN4O5+H, 597.2679; found 579.2661.

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Reference£º
Article; Zhou, Dong; Chu, Wenhua; Voller, Thomas; Katzenellenbogen, John A.; Tetrahedron Letters; vol. 59; 20; (2018); p. 1963 – 1967;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, cas is 763111-47-3, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,763111-47-3

General procedure: Intermediates 8 (1 eq) and respective 9-chloroacridine derivatives 4a-4f (1.1 eq) were added to a round flask, and then excessphenol was added as solvent. The reaction system was warmed up to 60 C until phenol was melted and stirred for 0.5 h under argonprotection. Then the mixture was warmed up to 120 C and continued to reaction for more 2 h. After the reaction was completed, themixture was added to ethyl ether drop by drop [2]. The precipitate was filtered and washed twice with new ethyl ether to give pureproducts 9a-9f, which were then characterized by 1H NMR, 13C NMR, melting point and high resolution mass spectrum (HRMS, ESI).

As the rapid development of chemical substances, we look forward to future research findings about 763111-47-3

Reference£º
Article; Dai, Qiuzi; Chen, Jiwei; Gao, Chunmei; Sun, Qinsheng; Yuan, Zigao; Jiang, Yuyang; Chinese Chemical Letters; vol. 31; 2; (2020); p. 404 – 408;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

6-Bromophthalazin-1(2H)-one, cas is 75884-70-7, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,75884-70-7

In a 10ml seal tube, 6-bromo-2H-pyridazin-l-one (108 mg, 480 muetaiotaomicron, Eq: 1.00), NH4OH (931 mg, 1.03 ml, 7.97 mmol, Eq: 16.6) and copper powder (30.5 mg, 480 muiotaetaomicron, Eq: 1.00) were combined with isopropyl alcohol (1 ml) to give a light brown suspension. The tube was sealed and the reaction was heated to 100 C overnight. The crude reaction mixture was concentrated in vacuo. The reaction mixture was diluted with sat NH4C1 and dichloromethane. The 2 phase mixture was filtered, the filtrate was separated and the aqueous extracted with dichloromethane (3X30 ml). SiC”2 was added to the aqueous phase and concentrated. The solid was suspended in hot dichloromethane/methanol 9: 1 and sonicated. Filtered and washed the filter cake with warm dichloromethane/methanol 9: 1. The filtrate was combined with the dichloromethane extracts and stripped to a light yellow powder. The powder was dried under vacuum at 25C for 1 hour to afford 62 mg (80%) of the desired product. MS +m/z: 162.1. (M+l)

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Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Zhi; CHIN, Elbert; ERICKSON, Shawn David; GABRIEL, Stephen Deems; MERTZ, Eric; WEIKERT, Robert James; WO2014/135483; (2014); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, cas is 763111-47-3, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,763111-47-3

4-(4-Fluoro-3-(piperazin-1-yl-carbonyl)-benzyl)pyridazine-1(2H)one (5) (0.78 g, 2.13 mmol) was added to a 25 ml three-necked flask.Dichloromethane (6.5 ml) and triethylamine (0.52 g, 5.14 mmol) were added, and the mixture was stirred and cooled to 1-10 C.Further, 3-methyl crotonyl chloride (304 mg, 2.56 mmol) was added dropwise, and the mixture was warmed to room temperature and stirred for 1 hour.TLC showed the reaction was complete; the reaction mixture was directly concentrated to dryness, and the residue was mixed with water and then stirred for 1 hour and then filtered.Obtained as an off-white solid.The yield was 63%.

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Patent; Shanghai Bobang Pharmaceutical Technology Co., Ltd.; Gao Heyong; Liu Zhende; Zhang Wensheng; (28 pag.)CN108383798; (2018); A;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

7-Bromophthalazin-1(2H)-one, cas is 152265-57-1, it is a common heterocyclic compound, the phthalazine compound, its synthesis route is as follows.,152265-57-1

10198] 7-l3romo- 1 -chlorophthalazine (9a) In a flame dried25 mE round bottom flask was added 7-bromophthalazin-1 (2H)-one (205 mg, 0.91 mmol), anhydrous acetonitrile (9 mE), and phosphorus oxychloride (0.3 mE, 3.22 mmol). The mixture was refluxed for 2 hours, then cooled to 00 C., diluted with dichloromethane (20 mE), and quenched with a drop- wise addition of sat. aq. NaHCO3 (20 mE). The biphasic mixture was stirred vigorously and allowed to warm to room temperature. Afier 1 hour the layers were separated and the aqueous was extractedwith dichioromethane (2×30 mE). The combined organic layers were washed with sat. aq. NaHCO3 (25 mE), washed with brine (20 mE), dried over Na2SO4, and concentrated to yield 9a as an orange solid in 91% yield. ?HNMR (500 MHz, CDC13) oe 9.45 (s, 1H), 8.49-8.5 1 (m, 1H), 8.10 (dd, J=8.8, 2.0 Hz, 1H), 7.91 (d, J=8.8 Hz, 1H). ECMS found 242.9 [M+H].

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Patent; Northeastern University; POLLASTRI, Michael P.; MEHTA, Naimee; DEVINE, William; WOODRING, Jennifer; SWAMINATHAN, Uma; US2015/259331; (2015); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

A common heterocyclic compound, the phthalazine compound, name is 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one,cas is 763111-47-3, mainly used in chemical industry, its synthesis route is as follows.,763111-47-3

4-(4-Fluoro-3-(piperazin-1-yl-carbonyl)-benzyl)pyridazine-1(2H)one (5) (0.78 g, 2.13 mmol) was added to a 25 ml three-necked flask.Dichloromethane (6.5 ml) and triethylamine (0.52 g, 5.14 mmol) were added, and the mixture was stirred and cooled to 1-10 C.Further, acryloyl chloride (230 mg, 2.56 mmol) was added dropwise, and the mixture was warmed to room temperature and stirred for 1 h.TLC showed the reaction was complete; the reaction mixture was directly concentrated to dryness, and the residue was mixed with water and then stirred for 1 hour and then filtered.Obtained as an off-white solid.The yield was 37%.

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Reference£º
Patent; Shanghai Bobang Pharmaceutical Technology Co., Ltd.; Gao Heyong; Liu Zhende; Zhang Wensheng; (28 pag.)CN108383798; (2018); A;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

A common heterocyclic compound, the phthalazine compound, name is 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,cas is 1242156-59-7, mainly used in chemical industry, its synthesis route is as follows.,1242156-59-7

NaH (60%), 108 mg, 2.72 mmol) was added portionwise to a solution of 6-tert-butyl-8-fiuoro- 2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 300.0 mg, 1.36 mmol) in DMF (3 mL) at 0 C. The mixture was heated at 70 C for 30 min. The mixture was cooled to room temperature, a solution of (2-bromo-5- bromomethyl-4-fiuoro-phenyl)-methanol (203 mg, 0.68 mmol) in DMF (2 mL) was added and the mixture was stirred for 2.5 h at room temperature. Water (5 mL) was added, and the mixture was extracted with EtOAc (3 x 15 mL). The combined organic layers were dried (Na2S04), filtered, and evaporated. The residue was purified by preparative HPLC to give 2-(4-bromo-2- fluoro-5-hydroxymethyl-benzyl)-6-tert-butyl-8-fluoro-2H-phthalazin-l-one (59 mg, 10%). MS calcd. for CzoftoB^NzC^ [(M+H)+] 437, obsd. 436.8.

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Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DOMINIQUE, Romyr; LOPEZ-TAPIA, Francisco Javier; MERTZ, Eric; SO, Sung-Sau; WO2014/76104; (2014); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem