Month: September 2020

17965-71-8, 3-Bromo-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 1 ,5-naphthyridin-3-amine:[0589] Commercial 3-bromo-[l,5]naphthyridine (1.00 g, 4.8 mmol) was dissolved in 50 mL dioxane. To it were added t-butyl carbamate (0.85 g, 7.2 mmol), cesium carbonate (3.13 g, 9.6 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol) and XantPhos (0.42g, 0.72 mmol). The mixture was degassed with Ar stream and stirred under Ar in 85C bath for 5 h. The mixture was concentrated, taken into 400 mL EtOAc and 200 mL water. The organic phase was separated, dried, concentrated and subjected to flash column (0-30% EtOAc in DCM) to obtain tert- butyl l,5-naphthyridin-3-ylcarbamate (1.04 g, 88% yield). This compound was treated with 50 mL 4N HCl in dioxane for overnight. To the suspension was poured diethyl ether 300 mL. The suspension was vigorously stirred. The solid product was collected by filtration as 1,5- naphthyridin-3 -amine di-HCl salt

17965-71-8, As the paragraph descriping shows that 17965-71-8 is playing an increasingly important role.

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 8-Chloro-3-methoxy-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

952059-69-7, General procedure: (Method C4) Synthesis of N’-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine In a 20 mL sealed tube was dissolved 8-chloro-3-methoxy-1,5-naphthyridine (70 mg, 360 mumol) in DMF (2.00 mL). To this was added N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine (124 mg, 396 mumol) and the reaction mixture was stirred at 70 C. for 17 h. Upon cooling to RT, the mixture was dissolved in DMF and purified using Gilson reverse phase chromatography. The product fractions were combined, concentrated and the resulting crude was extracted into DCM, washed 1* sodium carbonate, 1*H2O, dried with Na2SO4, filtered through fritted funnel, concentrated to yield N1-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as light yellow solid. MS [M+H]=471.0; Calc’d 470.5 for C29H22N60.

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

17965-71-8, 3-Bromo-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,17965-71-8

General procedure: To a solution of aryl bromide (0.3mmol) in anhydrous 1,4-dioxane (10mL) was added boronic acid (0.45mmol) and a solution of K3PO4 (130mg, 0.61mmol) in water (2mL). The mixture was purged with nitrogen gas for 5min. Pd(dppf)Cl2.CH2Cl2 (12mg, 0.015mmol) was added and the mixture was heated at 100C. After 5h, the reaction mixture was cooled to room temperature, filtered through celite and washed with ethyl acetate. The filtrate was washed with water (50mL), brine (50mL), dried (anhydrous Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC (C18 column, 20:80 acetonitrile/water with 0.1% formic acid). Compound containing fractions were lyophilized to afford the product. 5.1.2 1-(5-(1,5-Naphthyridin-3-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)-3-ethylurea (6) (0026) Synthesized from 4 and 5 following the general procedure for Suzuki coupling in 58% yield as a pale yellow solid. 1H NMR (400MHz, DMSO-d6) delta 9.52 (s, 1H), 9.05-9.04 (m, 1H), 8.82-8.81 (m, 1H), 8.50-8.46 (m, 4H), 8.26 (s, 1H), 7.85-7.82 (m, 1H), 7.62-7.59 (m, 1H), 3.27-3.19 (m, 2H), 1.12 (t, 3H, J=7.2Hz); 13C NMR (100MHz, DMSO-d6) delta 165.7, 153.7, 153.5, 151.6, 151.3, 149.1, 142.8, 142.4, 142.2, 142.0, 141.8, 138.7, 136.4, 136.1, 132.7, 125.7, 125.6, 124.5, 123.6, 120.9, 118.3, 115.6, 109.6, 33.4, 14.7. MS (ESI) m/z 445.1 (M+H)+; HRMS: calcd for C20H15F3N6OS (M+H)+, 445.1053; found, 445.1046. mp: 232.4-232.7C.

17965-71-8 3-Bromo-1,5-naphthyridine 12878818, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Article; Ho, Soo Yei; Wang, Weiling; Ng, Fui Mee; Wong, Yun Xuan; Poh, Zhi Ying; Tan, Sum Wai Eldwin; Ang, Shi Hua; Liew, Si Si; Joyner Wong, Yin Sze; Tan, Yvonne; Poulsen, Anders; Pendharkar, Vishal; Sangthongpitag, Kanda; Manchester, John; Basarab, Gregory; Hill, Jeffrey; Keller, Thomas H.; Cherian, Joseph; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 610 – 621;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.,15944-34-0

Intermediate 139: fert-Butyl ll-[2-f7-chloro-2-oxo-1.8-naphthyridin-l(2H)- yl)ethyl]piperidin-4-yl)carbamateA solution of 7-chloro-l,8-narhohthyridin-2(lH)-one FJ. Ore. Chem. 1990, 55, 4744- 4750] in dry DMF (20 mL) (540 mg, 3.0 mmol) at O0C was treated with sodium hydride (144 mg, 60% in mineral oil, 3.6 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction was cooled using an ice bath. A solution of 2- {4-[(fert-butoxycarbonyl)amino]piperidin-lyl} ethyl methanesulfonate in DMF (Intermediate 6), 0.33 mmol/ mL, 10 mL, 3.3 mmol) was then added over 1 hour. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with water and extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed with saturated sodium chloride solution (3 x 10 mL), dried over sodium sulfate and evaporated. Chromatography on silica gel using methanol in dichloromethane (0-15%) gave the title compound as a brown foam (711 mg, 58%).MS TES): 407 (MH)+ for C20H27ClN4O3 1H NMR rCDChU 1.42 (s, HH); 1.84 – 1.99 (m, 2H); 2.12 – 2.22 (m, IH); 2.22 -2.37 (m, 2H); 2.66 – 2.80 (m, 2H); 3.03 – 3.19 (m, IH); 3.39 – 3.55 (m, IH); 4.34 – 4.48 (m, IH); 4.62 (t, 2H); 6.72 (d, IH); 7.15 (d, IH); 7.61 (d, IH); 7.78 (d, IH).

The synthetic route of 15944-34-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/134378; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,952059-69-7

Step 1: N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide In a screw cap test tube were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (281 mg, 1443 mumol), N-(5-aminopyrimidin-2-yl)benzamide (281 mg, 1312 mumol) and pyridinium p-toluenesulfonate (494 mg, 1968 mumol) in butan-2-ol (2623 mul, 1312 mumol) then heated at 100 C. The reaction turned black in a minute. After 1 h, the reaction mixture showed full conversion to product according to LCMS. The reaction mixture was diluted with CH2Cl2, neutralized with sat. NaHCO3. An emulsion was formed but the two layers eventually separated. The aqueous phase was extracted 3 times with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated under reduce pressure to give a tan solid. The solid was triturated with hexane, filtered, and dried under vacuo. Brown solid was collected. LCMS confirmed the presence of the product, N-(5-(7-methoxy-1,5-naphthyridin-4-ylamino)pyrimidin-2-yl)benzamide. MS Calcd for C20H16N6O2: [M]+=372. Found: [M+H]+=373.

952059-69-7 8-Chloro-3-methoxy-1,5-naphthyridine 59427340, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.337958-60-8,5,7-Dichloro-1,6-naphthyridine,as a common compound, the synthetic route is as follows.

Intermediate 16: 1,1-Dimethylethyl (3S)-3-{[(7-chloro-1,6-naphthyridin-5-yl)oxy]methyl}-3-fluoro-1-piperidinecarboxylate[0413]1,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1-piperidinecarboxylate (1.406 g, 6.03 mmol) in DMF (20 ml) was added sodium hydride (0.313 g, 7.84 mmol) (60% dispersion in mineral oil). This was stirred for 15 min before adding 5,7-dichloro-1,6-naphthyridine (1.2 g, 6.03 mmol). This was warmed to room temp and stirred for 4 h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50 g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).[0415]LCMS: Rt=1.18 min, MH+=395.85, 337958-60-8

337958-60-8 5,7-Dichloro-1,6-naphthyridine 12204233, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.27225-00-9,2,7-Naphthyridin-1-amine,as a common compound, the synthetic route is as follows.,27225-00-9

4-Bromo-2,7-naphthyridin-1-ylamine32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25% aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

As the paragraph descriping shows that 27225-00-9 is playing an increasingly important role.

Reference£º
Patent; Merck Patent GmbH; Jonczyk, Alfred; Zenke, Frank T.; Amendt, Christiane; US2015/252041; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1569-16-0

: A mixture of 2-methyl-1,8-naphthyridine (250 mg, 1.734 mmol), 1H-indazole-5-carbaldehyde (253 mg, 1.734 mmol) and 4-methylbenzenesulfonamide (297 mg, 1.734 mmol) in toluene (4 mL) was heated at 110 ¡ãC overnight. The reaction was cooled to rt and diluted with EtOAc (15 mL). The solid was collected via filtering and rinsed with EtOAc (2 x 2 mL) and dried in vacuum to afford Intermediate E2A (415 mg, 1.524 mmol, 88percent yield). The crude product was used in the next reaction without further purification. LCMS (ES): m/z 273.2 [M+H]+.

1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; MORALES, Christian L.; HIGGINS, Mendi A.; MULL, Eric; (318 pag.)WO2018/89357; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

To a solution of 7-chloro-l,8-naphthyridin-2(lH)-one (2.7 g, 15.2 mmol) (J.Org.Chem. 1990, 55, 4744-4750) in N,N-dimethylformamide (4OmL) under nitrogen at O0C was added sodium hydride (0.73 g, 18.3 mmol). The slurry was stirred for ten minutes and then (2- bromoethoxy)-t-butyl dimethylsilane (4.3 g, 18.3 mmol) was added. The mixture was heated at 8O0C for two hours then cooled to room temperature. The reaction mixture was quenched with water and the product extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with 20% acetone in n-hexane gave the product as an oil (3.2 g, 62%).MS CES): 338 (MH+) for C16H23N2SiClO21H NMR fDMSO-d): delta ppm -0.00 (s, 6H); 0.81 (s, 9H); 3.91 (t, 2H); 4.53 (t, 2H); 6.80 (d,IH); 7.45 (d, 1 H); 8.06 (d, IH); 8.29 (d, IH).

15944-34-0, 15944-34-0 7-Chloro-1,8-naphthyridin-2-ol 13302322, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71964; (2008); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

EXAMPLESEXAMPLE l7-(4-Hydroxy-butoxy)-lH-[l,8]naphthyridin-2-one; To 1 liter (L) of n-methylpyrrolidinone was added 60% sodium hydride suspension (83.6g, 2.09moles). With external cooling to maintain 50C, 1,4-butanediol (3.39 moles) was added dropwise, causing offgassing. The mixture was stirred for 15 minutes at 60C, followed by addition of 7-Chloro-lH-[l,8]naphthyridin-2-one (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 146g, 0.813 moles) while stirring at 680C for 20 hours (h). To the mixture was added 5 liters of acetonitrile followed by filtration of a solid which was washed with a 50:50 mixture of acetonitrile and tetrahydrofuran. The solid was resuspended in 3 liters of tetrahydrofuran, to which was EPO added 3N HCl in methanol (290ml, 0.870 moles). After heating for 1 hour at 6O0C, the mixture was filtered thru celite, washed with 1 liter of tetrahydrofuran and concentrated to 500ml in volume. To the residue was added 1.5 liters of tetrahydrofuran, 1Og Darco activated charcoal, and 100ml Magnesol. After stirring at 40C for 30 minutes (min.), the mixture was filtered and washed with tetrahydrofuran and concentrated to 500ml in volume. To this residue was added 1 liter of acetonitrile followed by concentration of the mixture to 1 liter in volume. The resulting solid precipitate was filtered, washed with acetonitrile and ether, and dried at 50C giving 7-(4-Hydroxy-butoxy)-lH- [l,8]naphthyridin-2-one, 101g, (53% yield)., 15944-34-0

As the paragraph descriping shows that 15944-34-0 is playing an increasingly important role.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem