Month: August 2020

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

Example 109a 3-Bromo-5-(6-tert-butyl-8-fluoro-1-oxo-1,2-dihydrophthalazin-2-yl)pyridine-4-carbaldehyde 109a A sealed tube equipped with a magnetic stirrer was charged with 6-tert-butyl-8-fluoro-1,2-dihydrophthalazin-1-one 101h (220 mg, 1.0 mmol), 3,5-dibromopyridine-4-carbaldehyde (530 mg, 2.0 mmol), CuI (190 mg, 1.0 mmol), 4,7-dimethoxy-1,10-phenanthroline (244 mg, 1.0 mmol), Cs2CO3 (652 mg, 2.0 mmol) and dioxane (8 mL). After three cycles of vacuum/argon flush, the mixture was heated at 110 C. for 5 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3, V/V) to afford 109a (118 mg, 29.3%) as a solid. LCMS: [M+H]+ 406

With the synthetic route has been constantly updated, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong phthalazine compound,6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,1242156-59-7,Molecular formula: C12H13FN2O,mainly used in chemical industry, its synthesis route is as follows.,1242156-59-7

In a 1 L round-bottomed flask, 6-tert-butyl-8-fluorophthalazin-1(2H)-one (5.6 g, 25.4 mmol, Eq: 1.00) was combined with THF (300 ml) to give a colorless solution. Sodium hydride (1.12 g, 28.0 mmol, Eq: 1.1) was added. The reaction mixture was stirred at ambient temperature for 10 min 2-Fluoro-4-iodonicotinaldehyde (7.02 g, 28.0 mmol, Eq: 1.1) was added and the reaction mixture was stirred at ambient temperature for 1 h. The reaction was complete as determined by LCMS analysis. The reaction mixture was quenched with saturated NH4Cl. The reaction mixture was poured into 200 mL H2O and extracted 3X with CH2Cl2. The organic layers were washed with brine, then dried over Na2SO4 and concentrated in vacuo. The resultant bright yellow solid was transferred into a filter funnel and the flask washed twice with a small volume of EtOAc to ensure complete transfer of the solid into the funnel. The liquid was filtered through. The solid was triturated twice with Et2O and dried under vacuum to afford the desired product as a cream-colored solid (8.09 g, 17.9 mmol, 70.5 % yield). (M+H) = 452 m/e. H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.44 (s, 9 H) 7.49 – 7.54 (m, 1 H) 7.54 (d, J=1.77 Hz, 1 H) 8.03 (d, J=5.31 Hz, 1 H) 8.30 (d, J=2.53 Hz, 1 H) 8.37 (d, J=5.31 Hz, 1 H) 9.98 (s, 1 H).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong phthalazine compound,6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,1242156-59-7,Molecular formula: C12H13FN2O,mainly used in chemical industry, its synthesis route is as follows.,1242156-59-7

Example 101i 2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde 101i To a 10 mL round bottom flask were added 6-tert-butyl-8-fluoro-2H-phthalazin-1-one 101h (640 mg, 2.9 mmol), 2-chloro-6-fluorobenzaldehyde (506 mg, 3.2 mmol), and cesium carbonate (488 mg, 1.5 mmol). The flask was evacuated and backfilled with nitrogen three times then ethoxytrimethylsilane (684 mg, 5.8 mmol) and DMF (5 mL) were added to the reaction flask. The resulting mixture was heated to 60 C. After 4 h of stirring, the solution was allowed to cool down to ambient temperature and the reaction was quenched by addition of 2 mL of H2O drop-wise. The desired product started to precipitate from the DMF and water mixture. The solid was collected by filtration after cooling down to 5 C., and washed with DMF/water (2/1, 2 mL, pre-cooled to 6 C.) and H2O (2 mL). The filter cake was dried under vacuum oven at 65 C. for overnight to afford 519 mg (52%) of 101i as a yellow solid. MS: [M+H]+: 359

With the synthetic route has been constantly updated, we look forward to future research findings about 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO275,mainly used in chemical industry, its synthesis route is as follows.,75884-70-7

A dry 2-neck flask was evacuated and backflushed with argon (3X). Sodium t-butoxide (360 mg, 3.75 mmol), 6-bromophthalazin-l(2H)-one (338 mg, 1.5 mmol), (4-cyclohexylphenyl)methanamine (340 mg, 1.8 mmol), (+/-)BINAP (280 mg, 0.45 mmol) and Pd2(dba)3 (137 mg, 0.15 mmol) were added to the flask. Toluene (30 mL) was then added and the mixture was degassed with stirring under vacuum and backflushed with argon (3X). The reaction mixture was stirred at reflux for 3 hours and then allowed to cool to room temperature. The reaction mixture was poured onto water and EtOAc and extracted with EtOAc (3X) and then extracted with DCM (2X). The combined organic extract was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was slurred in DCM and filtered and the solid cake washed several times with DCM. The combined filtrate and washes were concentrated in vacuo to provide crude product, 6-((4-cyclohexylbenzyl)amino)phthalazin-l(2H)-one, as an off-white powder (118 mg).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO274,mainly used in chemical industry, its synthesis route is as follows.,75884-70-7

6-Bromo-l-chloro-phthalazine; A mixture of 6-Bromo-2H-phthalazin-l-one (2.5g), phosphorous oxychloride (11 mL) and diisopropyl ethyl amine (2 mL) was stirred at RT for 30 min then at 90 0C for3h. The reaction was then concentrated under reduced pressure, diluted with ethyl acetate and washed with a saturated solution OfNaHCO3, NH4Cl, and brine to afford the desired compound (2.0 g). TLC lambda/0.8 (EA/hexane 2/3).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazin-1(2H)-one,belong phthalazine compound

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

As a common heterocyclic compound, it belong phthalazine compound,6-Bromophthalazin-1(2H)-one,75884-70-7,Molecular formula: C8H5BrN2O,mainly used in chemical industry, its synthesis route is as follows.,75884-70-7

In a 50 mL pear-shaped flask, 6-bromophthalazin-l(2H)-one (214 mg, 951 muiotaetaomicron, Eq: 1.00) and CS2CO3(372 mg, 1.14 mmol, Eq: 1.20) were combined with DMF (3 ml) to give a light brown suspension. Methyl iodide (202 mg, 89.0 mu, 1.43 mmol, Eq: 1.50) was added and the reaction mixture was stirred at 25 C for 20 h. The reaction was diluted with dichloromethane and water. The aqueous layer was back-extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed with H20 (1 x 25 mL), dried over Na2S04and concentrated in vacuo. The crude material was recrystallized from dichloromethane to give a light yellow solid. The solid was dried under vacuum to afford 112 mg (49%) of the desired product as a light yellow crystalline solid.MS +m/z: 239/241 (M+l)

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
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

As a common heterocyclic compound, it belong phthalazine compound,6-Bromophthalazin-1(2H)-one,75884-70-7,Molecular formula: C8H5BrN2O,mainly used in chemical industry, its synthesis route is as follows.,75884-70-7

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).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
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

As a common heterocyclic compound, it belong phthalazine compound,6-Bromophthalazine,19064-74-5,Molecular formula: C8H5BrN2,mainly used in chemical industry, its synthesis route is as follows.,19064-74-5

A glass microwave reaction vessel was charged with 6-bromophthalazine (1.0 g, 5 mmol), tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (4.0 g, 7 mmol), DMF (4 mL), cesium fluoride (1.0 g, 10 mmol), copper(I) iodide (0.2 g, 1.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.2 mmol). The reaction mixture was stirred and heated at 100 C. overnight. The mixture was diluted with DCM (20 mL) and water (5 mL) and filtered through Celite. The organic solution was evaporated under reduced pressure, and the residue was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 10% MeOH in DCM to provide the title compound (1.19 g, 76%). LCMS (M+H+) 329.3 calc. for C16H16N4O2S 329.3; 1H NMR (400 MHz, CDCl3) delta ppm 9.50 (s, J=13.69 Hz 1H), 9.46 (s, 1H), 8.01 (d, J=1.37, Hz 1H), 7.92 (d, J=8.41 Hz, 1H), 7.81 (s, 1H), 7.58 (s, 1H) 1.40 (s, 9H).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazine,belong phthalazine compound

Reference£º
Patent; AMGEN INC.; US2007/173506; (2007); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong phthalazine compound,6-Bromophthalazine-1,4-diol,76240-49-8,Molecular formula: C8H5BrN2O2,mainly used in chemical industry, its synthesis route is as follows.,76240-49-8

To a solution of 6-bromo-2,3-dihydrophthalazine-1,4-dione (CAS 76240-49-8, 36.0 g, 150 mmol) and Et3N (37.5 g, 375 mmol) in DCM (1.0 L) was added Tf20 (42.3 g, 150 mol) dropwise over 1 h. The mixture was stirred at 0 C for 2 h and then kept at 15 C for 16 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by flash column(petroleum ether: EtOAc from 5:1 to 3:1) to give a mixture of the title compounds (9.0 g, 16% yield) as a white solid; A solution of (6-bromo-4-oxo-3H-phthalazin- 1 -yl) trifluoromethanesulfonate and (7-bromo-4-oxo-3H-phthalazin-1-yl) trifluoromethanesulfonate (9.0 g, 24.1 mmol), (4-tert-butylphenyl)boronic acid (CAS 123324-71-0, 4.2 g, 24.1 mmol), Cu(AcO)2 (8.6 g, 48.2 mmol) and TEA (7.2 g, 72.3 mol) in THF (100 mL) was stirred at 15 C for 16 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether: EtOAc from 20:1 to 10:1) to give [6-bromo-3-(4-tert-butylphenyl)-4-oxo-phthalazin- 1 -yl] trifluoromethanesulfonate (4.0 g, 33.0% yield) and [7- bromo-3 -(4-tert-butylphenyl)-4-oxo-phthalazin- 1 -yl] trifluoromethanesulfonate (3.0 g, 25% yield) as white solids. MS (m/e): 505.1 and 507.1 (M+H)+

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromophthalazine-1,4-diol,belong phthalazine compound

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CUMMING, John G.; LIN, Xianfeng; LIU, Haixia; NAJERA, Isabel; QIU, Zongxing; SANDRIN, Virginie; TANG, Guozhi; WU, Guolong; (204 pag.)WO2018/1948; (2018); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong phthalazine compound,7-Bromophthalazin-1(2H)-one,152265-57-1,Molecular formula: C8H5BrN2O,mainly used in chemical industry, its synthesis route is as follows.,152265-57-1

A mixture of compound 50-d (600mg, 2.67mmol) and POCl3 (8mL) was heated to reflux for 1.5h, cooled toroom temperature and concentrated under reduced pressure. The residue was dissolved in DCM (40mL), washed inturn with saturated sodium bicarbonate (40mL) and saturated brine (10mL), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure. The residue was purified by silica column chromatography (PE:EA = 3:1) togive compound 50-c (500mg, yield 75%). LC-MS (ESI): m/z = 243 [M+H]+.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Bromophthalazin-1(2H)-one,belong phthalazine compound

Reference£º
Patent; Shanghai Yingli Pharmaceutical Co. Ltd.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WU, Tianzhi; (104 pag.)EP3275867; (2018); A1;,
Phthalazine – Wikipedia
Phthalazine | C8H6N2 – PubChem