Heterocyclic Building Blocks-phthalazine

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.

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

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.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

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

75884-70-7, 6-Bromophthalazin-1(2H)-one is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 60: Synthesis of 6-(4-Methoxy-benzylamino)-2H-phthalazin-l-one; A mixture of 6-bromo-2H-phthalazin- 1 -one (50mg, 0.22 mmol), 4- methoxybenzylamine (0.03OmL, 0.24 mmol), Pd2(dba)3 (20mg, 0.022 mmol), rac-BINAP (41mg, 0.066 mmol) and NaOt-Bu (52mg, 0.55 mmol) in toluene (1OmL) was heated at reflux for 3h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with NaHCO3 (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound (22mg, 35%). 1H-NMR (DMSO-J6) delta: 12.1 (s, IH), 8.05 (s, IH), 7.88 (d, IH), 7.30 (m, 3H), 7.10 (dd, IH), 6.90 (d, 2H), 6.75 (s, IH), 4.20 (d, 2H), 3.85 (s, 3H); m/z (M+l) = 282.22.

As the paragraph descriping shows that 75884-70-7 is playing an increasingly important role.

Reference£º
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

76240-49-8, 6-Bromophthalazine-1,4-diol is a phthalazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 78: ^Chloro-beta-tS-piperidin-l-ylmethyl-benzylaminoJ-lH-phthalazin-l- one; 6-Bromo-4-chloro-2H-phthalazin-l-one; A mixture of 6-bromo-2,3-dihydro-phthalazine-l,4-dione (42.8 g, 178 mmol) in POCl3 (300 mL) was heated at reflux for 3h. The mixture was allowed to cool and concentrated. The residue was taken up in EtOAc (400 mL) and water (200 mL), and neutralized with sodium bicarbonate. The layers were separated, aqueous layer was extracted with EtOAc (3×200 mL), and combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in dioxane (300 mL) and 2N NaOH (25OmL). The mixture was heated at 500C for 30min, poured into water (3L), and stirred for 15 min. Solid was filtered and dried in vacuum at room temperature to give title compound as a greenish solid (12.0 g, 24.3%). M/z (M+l) = 259.32.

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

Reference£º
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
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

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.

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
Article; Zhou, Dong; Chu, Wenhua; Voller, Thomas; Katzenellenbogen, John A.; Tetrahedron Letters; vol. 59; 20; (2018); p. 1963 – 1967;,
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

To the solution of sodium methoxide (0,0151 mol of Na in dry methanol 40 ml) was added 2/f-phthalazin-l-on (0,01368 mol). The mixture was stirred and heated at reflux for 30 minutes. Then solvent was evaporated and the obtained sodium salt of phthalazinone was dried in vacuum dessicator. To the dried salt anhydrous dimethylformamide (20 ml) and N-2-bromoethyl)phthalimide (0,01505 mol) were added and the mixture was refluxed for 6 hours. After cooling to ambient temperature water (100 ml) was added to the reaction mixture. The product was filtrated and purified by recrystallization.2-[2-(l-Oxo-leta-phthalazin-2-yl)-ethyl]-isoindole-l,3-dione (compound no. 9) Found: C 67.65; H 4.15, N 13.19.

As the paragraph descriping shows that 119-39-1 is playing an increasingly important role.

Reference£º
Patent; UNIWERSYTET LODSKI; WO2009/51504; (2009); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem