Category: 1569-16-0

Name is 2-Methyl[1,8]-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine 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)+.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; Pharmacia Corporation; US6921767; (2005); B2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2-Methyl[1,8]-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

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]+

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/16610; (2007); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.,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).

With the complex challenges of chemical substances, we look forward to future research findings about 1569-16-0,belong naphthyridine compound

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

As a common heterocyclic compound, it belong naphthyridine compound,2-Methyl[1,8]-Naphthyridine,1569-16-0,Molecular formula: C9H8N2,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

STEP 2. SYNTHESIS OF (E)-1-ETHOXY-2- (1, 8-NAPHTHYRIDIN-2- YL) ethanol. To the product from step 1, (81.5 G, 0.57 mol) in anhydrous THF (1.9 L) at – 40 C under Ar gas was added lithium bis (trimethylsilyl) amide (1 M in THF, 1.2 L, 1.2 MOL). After stirring for 30 min at-40 C, DIETHYLCARBONATE (72.5 mL, 0.60 mol) was added. The temperature of the reaction mixture was warmed up to 0 C and stirred for 2 h. The reaction mixture was quenched into saturated aq. NH4CI (700 mL) and the THF removed under reduced pressure. The resulting mixture was extracted with EtOAc (3 x 700 mL). The organic layers were combined, washed with brine, dried over NA2SO4, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography using 50percent EtOAc/hexane to give a yellow solid (81.2 g, 0.38 mol, 66percent).APOS;H NMR (400 MHz, DMSO-d6) 8 1.22 (t, 3H), 4.11 (q, 2H), 4.89 (s, 1H), 6.78 (d, 1H), 7.15 (dd, 1H), 7.47 (d, 1H), 7.80 (d, 1H), 8.36 (d, 1H), 11.8 (bs, 1H). LC-MS (MH+) = 217.

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

Reference£º
Patent; PHARMACIA CORPORATION; WO2004/58761; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

1569-16-0, A solution of Int-19A (0.300 g, 2.08 mmol), commercially available ethyl 4-formyl-lH- pyrrole-2-carboxylate (0.348 g, 2.08 mmol), and 4-methylbenzenesulfonamide (0.356 g, 2.08 mmol) in toluene (4.5 mL) was stirred at reflux for 21 h. After cooling to room temperature, the precipitate was collected by filtration, triturated with DCM (2x) and dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid which was used in the next step without further purification. NMR (500MHz, DMSO-cfe) delta 12.14 (br. s., 1H), 9.01 (dd, J = 4.3, 2.1 Hz, 1H), 8.41 – 8.28 (m, 2H), 7.82 (d, J = 16.2 Hz, 1H), 7.76 (d, J= 8.5 Hz, 1H), 7.52 (dd, J= 8.0, 4.1 Hz, 1H), 7.46 (s, 1H), 7.24 – 7.16 (m, 2H), 4.27 (q, J= 7.2 Hz, 2H), 1.31 (t, J= 7.0 Hz, 3H). HPLC retention time (Method 1): 1.973 mia; LCMS (ES): m/z 294.0 [M+H]+.

1569-16-0 is used more and more widely, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (95 pag.)WO2019/94319; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

: 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

With the rapid development of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

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

As a common heterocyclic compound, it belong naphthyridine compound,2-Methyl[1,8]-Naphthyridine,1569-16-0,Molecular formula: C9H8N2,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

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).

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

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

It is a common heterocyclic compound, the naphthyridine compound, 2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0 its synthesis route is as follows.,1569-16-0

A solution of selenium dioxide (8.61 g, 77.56 mmol) in 1,4 dioxane (140 mL) with 0.5 mL ofwater was stirred at 100 ¡ãC for 5 mm. The mixture was cooled down to 0 ¡ãC and 2-Methyl-I ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at100 ¡ãC for 5 h. Completion of the reaction was monitored by TLC. The reaction mixturewas filtered through celite bed, washed with EtOAc (50 mL) and concentrated. Theresulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brownsolid). 1H NMR (300 MHz, DMSO-d6): 6 10.18 (5, IH), 9.28-9.27 (m, IH), 8.74 (d, J = 8.1 Hz, IH), 8.63 (d, J= 8.1 Hz, IH), 8.11 (dd, J= 8.4, 1.2 Hz, IH), 7.83-7.79 (m, IH). LCMS:(Method B) 159.0 (M +H), Rt. 2.44 mm, 91 .59percent (Max). HPLC: (Method B) Rt 2.41 mm, 87.86percent (Max).

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2-Methyl[1,8]-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

Step 1: 2-Chloromethyl-1,8-naphthyridine A solution of 2-methyl-1,8-naphthyridine (Chem. Pharm. Bull., 19, 1857 (1971)), N-chlorosuccinimide (1.1 equivalent), and a catalytic amount of benzoylperoxide in CCl4 were irradiated at reflux with a 225 watt lamp for 5 hours. After cooling, the solid was filtered and the filtrate evaporated to dryness. The crude residue was chromatographed to give the title product.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; Merck Frosst Canada Inc.; US5273980; (1993); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine 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)+.

With the complex challenges of chemical substances, we look forward to future research findings about 1569-16-0,belong naphthyridine compound

Reference£º
Patent; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan F.; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; US2002/77321; (2002); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem