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Analyzing the synthesis route of 763111-47-3

The chemical industry reduces the impact on the environment during synthesis,763111-47-3,4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one,I believe this compound will play a more active role in future production and life.

763111-47-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, cas is 763111-47-3,the phthalazine compound, it is a common compound, a new synthetic route is introduced below.

Orapanib intermediate (B) (0.77 kg, 2.10 mol) obtained in step (1) and triethylamine (0.88 kg, 6.32 mol) were added to methylene chloride (5.0 L) and stirred to control temperature 15 CAdd dropwise cyclopropyl carbonyl chloride (0.35L, 3.83mo 1), the dropwise addition, the reaction was stirred at 20-30 C 3h.Add appropriate amount of water, stirring 2h, suction filtration to obtain olaparib (0.79kg, a yield of 87%, a purity of 99.7%).

Reference£º
Patent; Shiyao Group Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; Wang Liwei; Zhang Hongfen; Zheng Ligang; Ji Dehua; Sun Xiaowei; Yu Pu; Guo Xiaofeng; (8 pag.)CN106928149; (2017); A;,
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Some tips on 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one

763111-47-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,763111-47-3 ,4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, other downstream synthetic routes, hurry up and to see

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

Reference£º
Article; Yuan, Zigao; Chen, Shaopeng; Sun, Qinsheng; Wang, Ning; Li, Dan; Miao, Shuangshuang; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 25; 15; (2017); p. 4100 – 4109;,
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Application of (2S,3S)-Butane-2,3-diol

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%.

Reference£º
Patent; Shanghai Bobang Pharmaceutical Technology Co., Ltd.; Gao Heyong; Liu Zhende; Zhang Wensheng; (28 pag.)CN108383798; (2018); A;,
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New learning discoveries about 763111-47-3

example 2 B (1 eq) dissolved in anhydrous second grade nitrile, then adding to bromine methyl cinnamic acid methyl ester (1 eq) and DIEA (2 eq), under the protection of nitrogen reaction at room temperature 2 hours, the reaction produces a large amount of white precipitate. Slightly static delayed filtering and washing the filter cake to a small amount of acetonitrile, the title compound obtained (white solid, yield 64%).

Reference£º
Patent; Graduate School at Shenzhen, Tsinghua University; Jiang Yuyang; Yuan Zigao; Gao Chunmei; Chen Shaopeng; (23 pag.)CN106946792; (2017); A;,
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The important role of 763111-47-3

Glutaric anhydride (0.50 g, 4.37 mmol) and N,Ndiisopropylethylamine (2.28 mL, 13.11 mmol) were added to a solution of 4-[[4-Fluoro-3-(piperazine-1-carbonyl)phenyl]methyl]-2H-phthalazin-1-one (2) (1.60 g, 4.37 mmol) in dichloromethane (50 mL) and the reaction mixture and stirred for 30 minutes. Water (50 mL) was then added and the reaction mixture stirred for another 30 minutes. The reaction mixture was acidified with HCl to pH 2, the organic phase separated and the aqueous phase extracted with dichloromethane (3*30 mL). The combined organic phases were dried over MgSO4 and volatiles removed in vacuo. The resulting crude material was purified using silica chromatography (0%-30% MeOH/DCM), yielding the pure product as an off-white solid (1.52 g, 3.16 mmol, 72%).

Reference£º
Patent; THE GENERAL HOSPITAL CORPORATION; Reiner, Thomas; Keliher, Edmund J.; Weissleder, Ralph; US2013/309170; (2013); A1;,
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Application of 7-Nitro-1,2,3,4-tetrahydroquinoline

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, 763111-47-3

General procedure: Compound 4 (400 mg, 1.09 mmol, 1 eq) was dissolved in acetonitrile(10 ml), and then 5a-c (1 eq) and DIEA (2 eq) were added.The mixture was stirred at room temperature for 2 h, and then theprecipitate was filtered, washed with water, acetonitrile and ethylether, and dried to give products 6a-c.4.1.2.1. Methyl (E)-3-(4-((4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl) benzoyl)piperazin-1-yl)methyl)phenyl)acrylate(6a). White powder; yield 64%; mp 160-162 C; 1H NMR(400 MHz, DMSO-d6) d 12.60 (s, 1H), 8.26 (dd, J = 7.7, 1.5 Hz, 1H),7.96 (d, J = 7.7 Hz, 1H), 7.91-7.85 (m, 1H), 7.85-7.78 (m, 1H),7.72-7.60 (m, 3H), 7.46-7.40 (m, 1H), 7.36 (d, J = 8.0 Hz, 2H),7.31 (dd, J = 6.5, 2.3 Hz, 1H), 7.26-7.17 (m, 1H), 6.63 (d,J = 16.1 Hz, 1H), 4.32 (s, 2H), 3.73 (s, 3H), 3.67-3.56 (m, 2H), 3.51(s, 2H), 3.23-3.10 (m, 2H), 2.45-2.34 (m, 2H), 2.32-2.18 (m, 2H).19F NMR (376 MHz, DMSO-d6) d-119.83. 13C NMR (101 MHz,DMSO-d6) d 166.6, 163.63, 159.2, 156.2 (d, J = 245.4 Hz), 144.7,144.2, 140.4, 134.7 (d, J = 3.2 Hz), 133.3, 132.8, 131.4,, 129.2,129.0, 128.6 (d, J = 3.9 Hz), 128.2, 127.8, 126.0, 125.3, 123.7 (d,J = 18.3 Hz), 117.4, 115.9, 115.7, 61.2, 52.6, 52.0, 51.3, 46.5, 41.3,36.3. HRMS (ESI) m/z calculated for [M+H]+ 541.2251, found541.2227.

Application of Copper(I) bromide

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

4,4′-(((4,4′-(4,4′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(butanoyl))bis(piperazine-4,1- diyl-1-carbonyl))bis(4-fluoro-3,1-phenylene))bis(methylene))bis(phthalazin-1(2H)-one): (0224) [3]: (0225) [00132] A solution of 4,4′-(1,1,3,3-tetramethyldisiloxane-1,3-diyl)dibutyric acid (250 mg, 0.816 mmol) in dichlromethane(5 mL) was charged EDCI-HCl (396 mg, 2.042 mmol) and 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one (598 mg, 1.633 mmol) at room temperature and stirred for 1hh. After completion of the reaction (monitored by TLC), water (5 mL) was added in the reaction mixture and organic layer was separated to obtain crude compound. The crude compound was purified by CombiFlash chromatography using 1-10% MeOH in DCM to obtain 286mg, 38% yield of the title compound as an off white solid.1H NMR (400 MHz, DMSO-d6): delta 12.57 (s, 2H), 8.55 (d, J = 10.27 Hz, 2H), 8.23 (d, J = 7.83 Hz, 1H), 7.92-7.96 (m, 1H), 7.84-7.89 (m, 2H), 7.78-7.83 (m, 2H), 7.38-7.44 (m, 2H), 7.33 (br. s, 2H), 7.21 (t, J = 8.80 Hz, 2H), 4.44 (s, 2H), 4.30 (s, 2H), 3.49-3.62 (m, 14H), 3.33-3.38 (m, 4H), 3.08-3.18 (m, 2H), 2.25-2.38 (m, 4H), 1.44-1.55 (m, 2H), 0.46-0.54 (m, 2H), 0.14 (br. s, 3H), 0.13 (br. s, 3H), 0.04 (br. s, 3H), 0.03 (br. s, 3H); MS (ES+): m/z = 493.20 [Monomer M – 18]+; LCMS: tR = 0.792 min.

Reference£º
Patent; BLINKBIO, INC.; WANNER, Jutta; NGUYEN, Hanh, Nho; WERNER, Douglas, S.; OFORI, Leslie, Odame; (167 pag.)WO2017/214491; (2017); A1;,
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Some tips on 763111-47-3

4-(4-Fluoro-3-(piperazine-l-carbonyl)benzyl)phthalazin-l(2H)-one (10 mg, 0.0275 mmol) was mixed with HBTU (16 mg, 0.0413 mmol) triethylamine (40 mu, 0.3 mmol) and 4-iodo 3 phenyl propionic acid (7.6 mg, 0.0275 mmol) in 400 mu of acetonitrile, and the solution was stirred overnight at room temperature. The crude product was then purified by preparative HPLC and the isolated product dried at vacuum to obtain a white solid (7.5 mg, 45%). H NM R (CDCI3) delta = 9.71 (s, 1H), 8.40-8.38 (d, 1H), 7.70-7.69 (m, 2H), 7.64-7.63 (m, 1H), 7.55-7.52 (m, 2H), 7.27-7.25 (m, 2H), 7.00-6.97 (m, 1H), 6.91-6.87 (m, 2H), 4.20 (s, 2H), 3.64-3.11 (m, 8H), 2.87-2.85 (m, 2H), 2.63-2.47 (m, 2H). LC-ESI-MS (+) m/z = 647.1 [M+Na+]+. HRMS-ESI [M+Na+]+ m/z calculated for [C29H26FI N403Na]+ 647.0931, found 647.0941.

Reference£º
Patent; MEMORIAL SLOAN KETTERING CANCER CENTER; REINER, Thomas; LEWIS, Jason S.; WEBER, Wolfgang; RODRIGUEZ, Beatriz Salinas; CARNEY, Brandon; CARLUCCI, Giuseppe; (89 pag.)WO2016/33293; (2016); A1;,
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The important role of 763111-47-3

4-[[4-Fluoro-3-(piperazine-1-carbonyl)phenyl]methyl]-2H-phthalazin-1-one (11) (250 mg, 0.68 mmol), HBTU (337 mg, 0.89 mmol) and triethylamine (285 muL, 1.18 mmol) were added to a solution of 6-hydroxyhexanoic acid (180 mg, 1.36 mmol) in DMF (3.0 mL) and the reaction mixture was stirred at room temperature for 60 minutes, before dichloromethane (8 mL) and water (8 mL) were added, the organic phase separated and washed with water (3*8 mL). The organic phase was dried over MgSO4, volatiles removed in vacuo and the resulting crude material purified via HPLC, yielding the title compound as a clear solid (55.6 mg, 0.12 mmol, 17%).

Reference£º
Patent; THE GENERAL HOSPITAL CORPORATION; Reiner, Thomas; Keliher, Edmund J.; Weissleder, Ralph; US2013/309170; (2013); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

New learning discoveries about 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, 2-butenyl chloride (268 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 37%.