Category: 1569-16-0

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.,1569-16-0

The compound was prepared according to the procedure as described in WO 0033838. To a solution of 2-methyl-1,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35 ml) was added 10percent Pd/C, and the reaction mixture was stirred under H2 (10 psi) for 24 hours. Palladium was filtered out through celite and washed with excess ethanol. The filtrate was concentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) delta 1.82-1.87 (m, 2H), 2.22 (s, 3H), 2.65-2.76 (m, 2H), 3.33-3.36 (m, 2H), 6.32 (d,1H, J=7.25 Hz), 7.07 (d, 1H, J=7.38 Hz). Mass spectrometry: 149.15 (M+H)+.

The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nagarajan, Srinivasan R.; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; Yi, Yu; Huff, Renee M.; Desai, Bipinchandra N.; Devadas, Balekudru; Parikh, Mihir D.; Penning, Thomas; US2004/92538; (2004); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

To a solution of 2-methyl-1 ,8-naphthyridine (3.0 g, 20.7 mmol) in CH2CI2 (300 ml) was added Lambda/-chlorosuccimide (11.1 g, 81.6 mmol) and AIBN (15 mg). The reaction was refluxed for 4h with additional AlBN (7mg) added each hour, followed by reflux for 3Oh. The cooled reaction solution was washed well with aqueous Na2COs, brine, dried over MgSO4, and concentrated to give the desired product (5.12g, 100percent) as a tan solid:LC/MS (ES) m/z 247.2 [M+H]+

1569-16-0, The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/16610; (2007); A2;,
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

The mixture of 2-methyl-l,8-naphthyridine (85 mg, 0.586 mmol), E25A (128 mg, 0.586 mmol), and 4-methylbenzenesulfonamide (100 mg, 0.586 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by reverse phase ISCO (26 g C18 30 min gradient from 100percent A: 0percent B to 0percent A: 100percent B (A = 90percent H2O/10 percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E25B (18 mg, 5percent) as a minor byproduct. LCMS (ES): m/z 516.2 [M+H]+.

The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); 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

In a 25 mL microwave reaction tube,Adding 2-methylnaphthyridine,Salicylaldehyde 0.5 g (4 mmol) and 10 ml acetic anhydride,Forming an orange-red solution,At a controlled temperature of 130 ¡ã C,Microwave power 50W, microwave reaction 40min,With the thin layer of the reaction process to monitor;After the reaction,The solvent was concentrated under reduced pressure to remove acetic anhydride,Oil-like viscous liquid,Dissolved with hot ethanol,Then recrystallized from acetone,Precipitation of yellow powder,That is, 2- (2′-hydroxystyryl) naphthyridine probe reagent,Yield 35percent.

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

Reference£º
Patent; Guizhou University; Ceng, Xi; Ruan, Qin; Mou, Lan; Li, Zhao; Zhang, Hong; (29 pag.)CN106045996; (2016); A;,
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 stirred solution of 2-methyl-l,8-naphthyridine (57.5 g, 399 mmol) (available from Manchester Organics) and ( ?)-fe/ -butyl 3-(iodomethyl)pyrrolidine-l-carboxylate (124.2 g, 399 mmol) (Intermediate 1) in THF (1 L) was cooled to 0 ¡ãC and treated under nitrogen with a solution of lithium bis(trimethylsilyl)amide in THF (1M, 399 ml_, 399 mmol) over 20 min and the reaction mixture was stirred at 0 ¡ãC for 3 h. The reaction was quenched with saturated ammonium chloride solution (500 ml.) and water (500 ml.) and ethyl acetate (1 L) was added. The layers were separated and the aqueous phase was extracted with further ethyl acetate (1 L). The combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The residual brown oil (162 g) was purified by chromatography on a silica cartridge (750 g) eluting with a gradient of 0 – 100 percent [ethyl acetate in (5percent MeOH – 95 percent ethyl acetate)] over 8 column volumes. The appropriate fractions were combined and evaporated in vacuo to give the title compound (46.65 g, 36percent) as an orange solid: LCMS (System A) RT = 0.99 min, 97percent, ES+ve m/z 32S (M+H)+, [a]D20 = + 22 (c 1.00 in EtOH).

The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; FALLON, Brendan John; PRITCHARD, John Martin; WO2014/154725; (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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.,1569-16-0

a 2-Methyl-8-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,8-naphthyridine A mixture of 2-methyl-1,8-naphthyridine (J. Chem. Soc. (C) 1966, 315; 5.13 g, 35.58 mmole), 10percent Pd/C (1.14 g, 1.07 mmole), and absolute EtOH (70 mL) was deoxygenated through three evacuation/H2 purge cycles, then was stirred briskly under a balloon of H2. After 18.5 hr, the mixture was filtered through celite.(R)., and the filter pad was washed sequentially with absolute EtOH and EtOAc. The filtrate was concentrated to dryness, and the residue was reconcentrated from EtOAc to leave an off-white solid (5.25 g). A solution of the above material (5.25 g), di-tert-butyl dicarbonate (15.53 g, 71.16 mmole), and CH2Cl2 (10 mL) was concentrated on the rotavap to remove the solvent, and the oily residue was heated under N2 in an oil bath set at 55-60¡ã C. After 45 hr, the reaction was cooled to RT, and the residue was flash chromatographed on silica gel (40percent EtOAc/hexanes). The title compound (4.90 g, 55percent) was obtained as a light yellow solid: 1H NMR (300 MHz, CDCl3) delta7.27 (d, J=7.6 Hz, 1H), 6.81 (d, 7.6 Hz, 1H), 3.69 -3.79 (m, 2H), 2.65-2.75 (m, 2H), 2.48 (s, 3H), 1.83-1.98 (m, 2H), 1.52 (s, 9H), MS (ES) m/e 249 (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; SmithKline Beecham Corporation; US6495560; (2002); B1;,
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

2-Methyl-1,8-naphthyridine (1.1592 g, 8.0 mmol) and SeO2 (1.2452 g, 11.2 mmol) were added to 20 mL of 1,4-dioxane. The mixture were refluxed for 4 h in nitrogen atmosphere and filtered. The filtrate was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, ethyl acetate) (0.71 g, 56.6percent yield). Characterization of 1,8-naphthyridine-2-aldehyde: HRMS (EI) m/z: calcd for C9H7N2O [M+H]+, 159.0588; found, 159.0561. 1H NMR: (400 MHz; DMSO; TMS) 10.15 (s, 1H), 9.24-9.26 (m, 1H), 8.71 (d, 1H), 8.60-8.62 (m, 1H), 8.08 (d, 1H), 7.78-7.80 (m, 1H). 13C NMR (100 MHz, DMSO): 194.3, 155.8, 155.5, 155.0, 140.5, 138.3, 125.6, 124.9, 118.5.

1569-16-0, As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Article; Liu, Xingjiang; Chen, Mingxing; Liu, Ziping; Yu, Mingming; Wei, Liuhe; Li, Zhanxian; Tetrahedron; vol. 70; 3; (2014); p. 658 – 663;,
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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.,1569-16-0

The mixture of 2-methyl-l,8-naphthyridine (51 mg, 0.352 mmol), E5B (69 mg, 0.352 mmol), and 4-methylbenzenesulfonamide (60 mg, 0.352 mmol) in DME (5 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu C18 30 x l00 mm; 10 min gradient from 85percent A: 15percent B to 0percent A: 100percent B (A = 90percent H2O/I O percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E5C (16 mg, 14percent). LCMS (ES): m/z 323.3 [M+H]+.

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

A stirred solution of 2-methyl-1,8-naphthyridine (57.5 g, 399 mmol) (available from Manchester Organics) and (R)-tert-butyl 3-(iodomethyl)pyrrolidine-1-carboxylate (124.2 g, 399mmcl) (Intermediate 1) in THF (1 L) was cooled to 0 ¡ãC and treated under nitrogen with a solution of lithium bis(trimethylsilyl)amide in THE (1M, 399 mL, 399 mmcl) over 20 mm and the reaction mixture was stirred at 0 ¡ãC for 3 h. The reaction was quenched with saturated ammonium chloride solution (500 mL) and water (500 mL) and ethyl acetate (1 L) was added. The layers were separated and the aqueous phase was extracted with further ethyl acetate (1 L). The combinedorganic layers were dried (MgSO4), filtered and evaporated in vacuo. The residual brown oil (162 g) was purified by chromatography on a silica cartridge (750 g) eluting with a gradient of 0 ? 100percent [ethyl acetate in (5percent MeOH ? 95percent ethyl acetate)] over 8 column volumes. The appropriate fractions were combined and evaporated in vacuo to give the title compound (46.65 g, 36percent) as an orange solid: LCMS (System A) RT=0.99 mm, 97percent, ES+ve m/z328 (M+H)?, [aiD2¡ã = + 22 (c 1.00in EtOH).

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; CAMPBELL, Ian Baxter; CAMPBELL-CRAWFORD, Matthew Howard James; HANCOCK, Ashley Paul; LEMMA, Seble; MACDONALD, Simon John Fawcett; PRITCHARD, John Martin; PROCOPIOU, Panayiotis Alexandrou; (64 pag.)WO2016/46230; (2016); 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

[00228] A solution of 2-methyl-l,8-naphthyridine (5.0 g, 34.7 mmol) in tetrahydrofuran (60 mL) was stirred at -78 ¡ãC and MeLi (2 M solution in tetrahydrofuran, 52 mL, 104 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with water (50niL), extracted with ether (3 x 50 rnL) and the combined the organic layers were dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by flash chromatography eluting with ethyl acetate:petrol ether (1 : 10) to give the title compound as a white solid (4.55 g, 82percent). MS (ESI): m/z 161 [M + H]+.

1569-16-0, The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John Emmerson; JONES, Philip; WO2014/85284; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem