Category: phthalazine

1242156-59-7, 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred suspension of NaH (60%, 182 mg, 4.54 mmol) in DMF (1 mL) was added dropwise a solution of 6-tert-butyl-8-fluoro-2H-phthalazin-l-one (which may be prepared as described in Berthel, S. et al. US 20100222325 Column 139; 500 mg, 2.27 mmol) in DMF (1.5 mL) at 0 C. The mixture was heated to 70 C and stirred for 30 min. The mixture was cooled to room temperature, a solution of 5-bromo-2-bromomethyl-l,3-difluoro-benzene (715 mg, 2.5 mmol) in DMF (1.5 mL) was added and the mixture was stirred for 4 h at room temperature. The mixture was cooled and cold water (5 mL) was added. The mixture was extracted with EtOAc and the organic extract was dried, and evaporated. The residue was purified by chromatography (silica gel, 5-10% EtOAc/hexane) to give 2-(4-bromo-2,6-difluoro-benzyl)-6-tert-butyl-8-fluoro-2H- phthalazin-l-one (555 mg, 57%) as a yellow solid. MS calcd. for Ci9Hi7BrF3N20 [(M+H)+] 425, obsd. 425.

1242156-59-7 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one 59473765, aphthalazine compound, is more and more widely used in various.

Reference£º
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

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.

A solution of 6-bromophthalazine-1(2H)-one (0.25 g, 1.11 mmol), potassium vinyl trifluoroborate (0.446 g, 3.33 mmol) and K2CO3 (0.46 g, 3.33 mmol) in DMSO (2 mL) was degassed with argon for 20 min at RT. PdCl2(dppf) (0.04 g, 0.055 mmol) was added at RT, and the reaction mixture was heated to 80 C. for 2 h. The reaction mixture was cooled to RT and filtered through celite bed under vacuum and washed with ethyl acetate. The reaction mixture was extracted with ethyl acetate and the combined ethyl acetate layer dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. The crude compound was purified by column chromatography (SiO2, 100-200 mesh; 50% ethyl acetate/petroleum ether) to afford the title compound as a brown solid (0.12 g, 63%): 1H NMR (400 MHz, DMSO-d6) delta 13.61 (br, 1H), 8.33 (m, 1H), 8.19 (m, 1H), 8.01 (m, 2H), 6.97 (m, 1H), 6.15 (m, 1H), 5.56 (d, J=10.8 Hz, 1H); ESIMS m/z 172.93 ([M+H]+); IR (thin film) 1748, 1655, 3241 cm-1.

75884-70-7 6-Bromophthalazin-1(2H)-one 11535918, aphthalazine compound, is more and more widely used in various.

Reference£º
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

763111-47-3, 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAM PLE A.2. Compound c-1 (127l): 4-(4-fluoro-3-(4-(3-iodobenzoyl)piperazine-l-carbonyl)benzyl)- phthalazin-l(2H)-one. (0301) [0148] To a solution of 4-(4-fluoro-3-(piperazine-l-carbonyl)benzyl)phthalazin-l(2H)-one (10 mg, 0.0275 mmol), triethylamine (40 mu, 0.3 mmol) a nd H BTU (16 mg, 0.0413 mmol) in dimethyl formamide (DM F, 500 mu) was added to 3-iodobenzoic acid (6 mg, 0.0275 mmol). The mixtu re was stirred at room temperature for 20 h. The crude product was then purified by preparative HPLC and dried under vacuum, yielding a white solid (6.9 mg, 48% yield). 1H NM R (CDCIs) delta = 10.00 (s, 1H), 8.40-8.38 (m, 1H), 7.71-7.69 (m, 4H), 7.64-7.63 (m, 1H), 7.30-7.26 (m, 3H), 7.09 (m, 1H), 7.04-6.87 (m, 1H), 4.21 (s, 2H), 3.71-3.29 (m, 8H). LC-ESI-MS (+) m/z = 597.1 [M+H+]+. H RMS-ESI [M-H+]” m/z calculated for [C27H22FIN4O3]- 595.0642, found 595.0660.

The synthetic route of 763111-47-3 has been constantly updated, and we look forward to future research findings.

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;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.763111-47-3,4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one,as a common compound, the synthetic route is as follows.

EXAMPLE A.5. A solution of 4-iodophenyl acetic acid (6.5 mg, 0.048 mmol), EDC (10.5 mg, 0.055 mmol), NHS and 600 mu DMF was stirred for 30 min at room temperature. After this time, the 4-(4-fluoro-3- (piperazine-l-carbonyl)benzyl)phthalazin-l(2H)-one (10 mg, 0.0275 mmol) was added to the solution and the mixture was stirred at room temperature overnight. H20 (500 mu) was added, the mixture extracted with DCM (2 x 500 mu), and the combined extracts dried under vacuum. The crude mixture was purified by silica column chromatography (100% DCM), and the product obtained as a white solid (8.8 mg, 61%). 1H NMR (CDCI3) delta = 9.82 (s, 1H), 8.40-8.38 (m, 1H), 7.83-7.81 (d, 1H), 7.77- 7.75 (d, 1H), 7.70-7.69 (m, 2H), 7.63-7.56 (m, 3H), 7.00-6.89 (m, 3H), 4.20 (s, 2H), 3.63-3.11 (m, 8H), 2.84 (s, 2H). LC-ESI-MS (+) m/z = 632.9 [M+Na+]+. HRMS-ESI [M+H+]+ m/z calculated for [C28H24FIN403]+ 611.0955, found 611.0971.

763111-47-3 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one 11726399, aphthalazine compound, is more and more widely used in various.

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;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.76240-49-8,6-Bromophthalazine-1,4-diol,as a common compound, the synthetic route is as follows.

6-Bromo-2,3-dihydrophthalazine-1 ,4-dione (25. g, 0.10 mol) was added to a mixture of phosphorus oxychloride (100. mL, 1 .06 mol) and thionyl chloride (100. mL, 1 .37 mol) under nitrogen, cooled to 0 C. Once the initial exotherm had subsided the reaction mixture was allowed to warm to ambient temperature and then heated at 100 C for 4 h. The mixture was then cooled to ambient temperature and then concentrated in vacuo. The residue was dissolved in iPrOAc (350 mL) and washed with saturated sodium bicarbonate solution (added until effervescence stopped), a precipitate formed, the two layers were filtered to isolate the first crop of the intermediate. The organic layer was collected and distilled to dryness to give the second crop of the intermediate. The solids were combined and partitioned between 1 ,4-dioxane (200 mL) and 2 N NaOH (100 mL). The resulting mixture was heated at 40 C overnight and then cooled to ambient temperature and left to stand. The solid precipitate was filtered (first crop of product) and the resulting solution partitioned between EtOAc (250 mL) and water (200 mL). Further precipitate formed which was filtered and combined with the first crop of the product, the organic phase was separated and evaporated to dryness to give the second crop of the product. Product isolated is a mixture of two regioisomers, 7-bromo-4-chloro-2H-phthalazin-1 -one and 6- bromo-4-chloro-2H-phthalazin-1 -one, total yield isolated (17.6 g, 68.0 mmol, 66%).1 H NMR (300MHz, DMSO-d6) delta = 13.02 (s, 1 H), 12.98 (s, 1 H), 8.36 (d, J = 2.1 Hz, 1 H), 8.22 (dd, J = 2.1 , 8.6 Hz, 1 H), 8.17 – 8.1 1 (m, 3H), 7.93 (d, J = 8.7 Hz, 1 H). 1 :1 mixture of the two regioisomers.A stirred solution of 7-bromo-4-chloro-2H-phthalazin-1 -one and 6-bromo-4- chloro-2H-phthalazin-1 -one (8.82 g, 33.99 mmol) (-1 :1 mixture of isomers), tris(dibenzylideneacetone)dipalladium(0) (1 .56 g, 1 .7 mmol) and Xantphos (1 .97 g, 3.4 mmol) in 1 ,4-dioxane (200 mL) was degassed with nitrogen. N,N-Diisopropylethylamine (12.1 mL, 68.0 mmol) and benzyl mercaptan (7.98 mL, 68.0 mmol) were then added sequentially to the flask, and the resulting mixture was heated at 60 C for 18 h.The two flasks were combined and distilled to dryness, the residue was suspended in DCM (200 mL). The mixture was agitated for 30 min and filtered to give the desired product as a -1 :1 mixture of regioisomers 7-benzylsulfanyl-4-chloro-2H-phthalazin- 1 -one and 6-benzylsulfanyl-4-chloro-2H-phthalazin-1 -one. The mixture of isomers was recrystallised with acetic acid (200 mL), with a hot filtration to remove inorganic impurities. The resulting crystalline solid was filtered, washed with AcOH and minimal amount of ether, yielding a white solid which was dried in the vacuum oven at 40 C, 7-benzylsulfanyl-4- chloro-2H-phthalazin-1 -one (5.35 g, 17.7 mmol, 26%). 1H NMR (300MHz, DMSO-d6) delta = 12.86 (s, 1 H), 8.07 (d, J = 2.1 Hz, 1 H), 7.95 (dd, J = 2.1 , 8.6 Hz, 1 H), 7.87 (d, J = 8.6 Hz, 1 H), 7.49 – 7.44 (m, 2H), 7.37 – 7.24 (m, 3H), 4.49 (s, 2H)

The synthetic route of 76240-49-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.763111-47-3,4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one,as a common compound, the synthetic route is as follows.

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%.

The synthetic route of 763111-47-3 has been constantly updated, and we look forward to future research findings.

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

119-39-1, Phthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. Conventional Preparation of 1-Chlorophthalazine. One mole equivalent (10 g) of 1(2H)-phthalazinone and 7.7 mole equivalents (82.5 g, 50.1 mL) of phosphorus oxychloride were charged into a 100-mL, 3-necked flask fitted with a temperature probe and condenser. The slurry was stirred and heated to 70 C., and then the heat source was removed. The mixture was allowed to cool to room temperature, and then was poured in portions over 500 g of ice. After the initial addition of the reaction mixture, a violent exotherm was observed, and a portion of the solution spilled over the sides of the container. Ice quenching was completed with extreme caution but without further incident. Alternative workups were also examined. As a first alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. The resulting yellow slurry was added in portions to 3 volumes of cold, deionized water. Once again, control of exothermic reactions that occurred during this quenching step was difficult. As a second alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. To the resulting oily yellow paste was added 5 volumes of toluene, and the resulting biphasic solution was concentrated by heating at 45 C. under vacuum to remove the phosphorus oxychloridettoluene azeotrope. The process was repeated a second time. The resulting yellow paste solidified into an unworkable solid that was discarded. As a third alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. To the resulting oily yellow paste was added 2 volumes of toluene, and the resulting biphasic solution was concentrated by heating at 45 C. under vacuum to remove the phosphorus oxychloride/toluene azeotrope. The process was repeated a second time, and then 2 volumes of tetrahydrofuran were added. The resulting slurry was stirred and cooled to 0 C. and then was filtered to isolate a light yellow solid. The filtrate was treated as described in the following paragraph. The aqueous mixture was rendered basic by the addition of 5 N sodium hydroxide solution. A light yellow precipitate formed. The solid was isolated by extraction into dichloromethane and concentration of the resulting extracts to dryness. A moist cake of 1-chlorophthalazine was thus obtained in yields that ranged from 80% to 440% of theoretical. If the moist cake was allowed to dry, or if this material was not used immediately, it darkened and underwent degradation to a mixture of the desired product, 1-chlorophthalazine, and multiple by-products. To prevent this loss and contamination, freshly obtained, moist chloro compound was used immediately.

The synthetic route of 119-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nelson, Deanna J.; US2005/137397; (2005); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.119-39-1,Phthalazin-1(2H)-one,as a common compound, the synthetic route is as follows.

Example 1 Conventional Method of Preparation of Hydralazine Hydrochloride. A. Conventional Preparation of 1-Chlorophthalazine. One mole equivalent (10 g) of 1(2H)-phthalazinone and 7.7 mole equivalents (82.5 g, 50.1 mL) of phosphorus oxychloride were charged into a 100-mL, 3-necked flask fitted with a temperature probe and condenser. The slurry was stirred and heated to 70 C., and then the heat source was removed. The mixture was allowed to cool to room temperature, and then was poured in portions over 500 g of ice. After the initial addition of the reaction mixture, a violent exotherm was observed, and a portion of the solution spilled over the sides of the container. Ice quenching was completed with extreme caution but without further incident. Alternative workups were also examined. As a first alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. The resulting yellow slurry was added in portions to 3 volumes of cold, deionized water. Once again, control of exothermic reactions that occurred during this quenching step was difficult. As a second alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. To the resulting oily yellow paste was added 5 volumes of toluene, and the resulting biphasic solution was concentrated by heating at 45 C. under vacuum to remove the phosphorus oxychloride/toluene azeotrope. The process was repeated a second time. The resulting yellow paste solidified into an unworkable solid that was discarded. As a third alternative, after the reaction mixture reached room temperature, it was concentrated by heating at 45 C. under vacuum. To the resulting oily yellow paste was added 2 volumes of toluene, and the resulting biphasic solution was concentrated by heating at 45 C. under vacuum to remove the phosphorus oxychloride/toluene azeotrope. The process was repeated a second time, and then 2 volumes of tetrahydrofuran were added. The resulting slurry was stirred and cooled to 0 C. and then was filtered to isolate a light yellow solid. The filtrate was treated as described in the following paragraph. The aqueous mixture was rendered basic by the addition of 5 N sodium hydroxide solution. A light yellow precipitate formed. The solid was isolated by extraction into dichloromethane and concentration of the resulting extracts to dryness. A moist cake of 1-chlorophthalazine was thus obtained in yields that ranged from 80% to 440% of theoretical. If the moist cake was allowed to dry, or if this material was not used immediately, it darkened and underwent degradation to a mixture of the desired product, 1-chlorophthalazine, and multiple by-products. To prevent this loss and contamination, freshly obtained, moist chloro compound was used immediately.; Example 2 Novel Method for the Preparation of Hydralazine Hydrochloride. A. Novel Preparation of 1-Chlorophthalazine. One mole equivalent (250 g) of 1 (2H)-phthalazinone and 3.8 mole equivalents (775 g) of phosphorus oxychloride were charged into a 3-L, 3-necked flask fitted with a temperature probe and condenser. The slurry was stirred and heated to 80 C., maintained at that temperature for 30 minutes, and then the heat source was removed. Thin layer chromatographic analysis indicated that conversion to 1-chlorophthalazine was complete. The mixture was allowed to cool to room temperature, and 1.6 L of hexanes was added. The resulting slurry was stirred for several minutes, and the hexane layer was decanted. Addition of hexanes and decantation was repeated two more times. Then 1.6 L of tetrahydrofuran was added; as the solution was stirred, an off-white precipitate formed. The solid was isolated by filtration and washed with 250 mL of cold tetrahydrofuran to afford an 85-100% yield of 1-chlorophthalazine, the desired product, as an off-white powder that could be dried and characterized.;

The synthetic route of 119-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nelson, Deanna J.; Barbeau, Donald L.; US2005/137198; (2005); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

1242156-59-7, 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 100 mL round bottom flask series added compound 4-1 (1.77 g, 8.04 mmol), commercially available starting material 4-2 (1.40 g, 8.84 mmol) and cesium carbonate (1.90 g, 4.82 mmol). The flask was evacuated and back filled with nitrogen three times. Then ethoxytrimethylsilane (1.90 g, 16.07 mmol) and DMF (20 mL) were added to the reaction flask, and the resulting mixture was heated 62C. After 5 h stirring, the solution was allowed to cool down to ambient temperature and the reaction was quenched by addition 20 mL of water. The desired product started to precipitate from DMF and watermixture. The solid was collected by filtration after cooling down to 5C, and washed with water. The filter cake was dried under vacuum oven at 50C to afford crude compound 3 (2.88 g, yield:99.8%) as a light yellow solid which was used for next step without purification.

1242156-59-7 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one 59473765, aphthalazine compound, is more and more widely used in various.

Reference£º
Patent; CHEN, Yi; WO2015/50703; (2015); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem