Month: September 2020

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 13; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(6-methoxy-l,5-naphthyridin- 4~yloxy)phenyl] acetamide; A mixture of 4-chloro-6-methoxy-l,5-naphthyridine (0.08 g), JV-(I -ethyl-lH-pyrazol-4- yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide (0.113 g), 4-dimethylaminopyridine (0.151 g) and chlorobenzene (1 ml) was stirred and heated under argon to 140C for 14 hours. The resultant mixture was cooled to ambient temperature and partitioned between methylene chloride and 2N aqueous hydrochloric acid. The organic extract was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a solvent gradient from ethyl acetate to a 19:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound as a solid (0.018 g); 1H NMR Spectrum:5 (DMSOd6) 1.32 (t, 3H), 3.58 (s, 2H), 3.75 (s, 3H), 3.95 (s, 3H), 4.07 (q, 2H), 6.79 (m, IH), 6.91 (d, IH), 6.93 (d, IH), 7.29 (d, IH), 7.31 (d, IH), 7.41 (s, IH), 7.87 (s, IH), 8.28 (d, IH), 8.61 (d, IH), 10.01 (s, IH); Mass Spectrum: M+H+ 434., 249889-68-7

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-2-methoxy-1,5-naphthyridine

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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

A mixture of 2-methyl-1,8-naphthyridine (18.5 g, 128 mmole), 10percent Pd/C (5 g), and absolute EtOH (150 mL) was shaken under hydrogen (15 psi) on a Parr apparatus. After 24 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 to leave the title compound (18.85 g, 99percent) as an off-white solid: 1H NMR (300 MHz, CDCl3) delta 7.02 (d, J = 7.5 Hz, 1 H), 6.34 (d, J = 7.5 Hz, 1 H), 4.80 (br s, 1 H), 3.38 (m, 2 H), 2.74 (m, 2 H), 2.30 (s, 3 H), 1.88 (m, 2 H); MS (ES) m/e 149 (M + H)+.

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

Reference£º
Patent; SmithKline Beecham Corporation; EP1218005; (2004); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Chloro-1,8-naphthyridine, cas is 15936-10-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Description 94; 6-(1 8-Naphthyridin-2-yl) pvrimidin-4-amine; To a mixture of Description 92 (2.52 g, 15. 3 mmol), hexamethylditin (5.0 g, 15.3 mmol), lithium chloride (1.95 g, 45.9 mmol), and copper (I) iodide (291 mg, 1.53 mmol) in anhydrous 1,4-dioxane (50 ml) was added Pd (PPh3) 4 (884 g, 0.77 mmol). The mixture was de-gassed three times, and heated at 100C overnight. The mixture was cooled and diluted with EtOAc (120 ml) and washed with a 10% potassium fluoride solution (200 ml). The organic layer was washed with sat. NaCl (50 ml), dried over Na2SO4, filtered, and evaporated. The residue was taken up in anhydrous 1,4-dioxane (75 ml), and Description 93 (1.55 g, 7 mmol), lithium chloride (1.78 g, 42 mmol), and copper (I) iodide (266 mg, 1.4 mmol) added, followed by Pd (PPh3) 4 (808 mg, 0.7 mmol). The mixture was de-gassed 3 times and heated at 100C for 3 days. The mixture was poured into water (200 ml), and extracted with EtOAc (2 x 100 ml), the combined EtOAc layers were washed with water (150 ml), sat. NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica (eluent: 2% MeOH in DCM + 0.5% NH40H) to give the title compound (100 mg, 3%).’H NMR (360 MHz, DMSO-d6) 7.18 (2 H, br s), 7.66-7. 86 (3 H, m), 8.55 (1 H, dd, J 8.1 and 1. 8), 8. 58 (1 H, d, J4. 2), 8.64 (1 H, d, J8. 4), 9.16 (1 H, dd, J4. 2 and 2.1)., 15936-10-4

With the rapid development of chemical substances, we look forward to future research findings about 2-Chloro-1,8-naphthyridine

Reference£º
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

2-(2-(7-Methoxyquinolin-4-ylamino)ethyl)-6-phenylpyridazin-3(2H)- one. A mixture of 2-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one (60 mg, 743 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (55 mg, 282 mumol) in iPrOH (2 mL) was heated to 150 0C for 15 min under microwave. The mixture was filtered and the filtrate was chromatographed on silica with 2-5% (2N NH3-MeOH) in CH2Cl2 to give the product as a white solid (60 mg). MS (ESI pos. ion) calc’d for C2IHi9N5O2: 373.1; found 374.2 (MH+). 1H NMR (400 MHz, Chloroform-d) delta ppm 3.81 – 3.89 (m, 2 H) 3.92 (d, J=I.37 Hz, 3 H) 4.64 (t, J=5.48 Hz, 2 H) 6.54 (dd, 1 H) 7.03 (dd, J=9.78, 1.57 Hz, 1 H) 7.10 (s, 1 H) 7.39 – 7.48 (m, 4 H) 7.66 (dd, J=9.59, 1.56 Hz, 1 H) 7.70 – 7.79 (m, 2 H) 8.38 (t, 1 H) 8.46 (dd, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH. Ethyl 7-((benzo[d]thiazol-2-yl)thio)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (3) Yield: 86 %, M.P. = 184.7 C. HPLC: 99.6 % purity. FTIR (ATR, cm-1 ): 1736 (C=O, ester), 1624 (C=O, ketone), 1043, 806, 750. 1H-NMR (300 MHz, DMSO-d6): delta = 1.25 (3H, t, J= 7.05 Hz , -CH3), 4.22 (2H, q, J= 7.05 Hz , -CH2-), 6.96-7.08 (2H, m, phenyl H(3), H(5)), 7.54-7.59 (2H, m, benzothiazole H(5), H(6)), 7.60-7.69 (1H, m, phenyl H(6)), 7.96-8.00 (1H, s, benzothiazole H(4), H(7)), 8.40 (1H, d, J= 8.85 Hz, naphthyridine H(5)), 8.64 (1H, s, naphthyridine H(2).13C-NMR (75 MHz, DMSO-d6): delta = 14.60, 60.81, 105.14 (q, J= 23.5 Hz), 112.49 (d, J= 22.6 Hz), 113.04, 121.01 (d, J= 19.1 Hz), 121.77 (d, J= 2.9 Hz), 122.04, 123.26, 124.28 (d, J= 13.3 Hz), 126.65, 127.14, 131.69 (d, J= 10.3 Hz), 137.28, 146.16, 149.15 (d, J= 21.0 Hz), 149.62, 152.03, 152.98 (d, J= 253.5 Hz), 155.09 (d, J= 3.4 Hz), 157.97 (dd, J= 250.7 Hz- 13.4 Hz), 162.77 (dd, J= 248.1 Hz- 11.6 Hz), 163.80, 173.15. HRMS (m/z): [M+H]+ calcd for C24H14N3O3S2F3: 514.0501; found 514.0492.

100491-29-0, With the rapid development of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

253-72-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.253-72-5,1,6-Naphthyridine,as a common compound, the synthetic route is as follows.

EXAMPLE 3 Preparation of 5,6,7,8-tetrahydro-6-(3-butenyl)-1,6-naphthyridine (Compound No. 14) A mixture of 1,6-naphthyridine (3.9 g, 0.03 mol) and 4-bromo-1-butene (4.9 g, 0.036 mol) was heated at 70¡ã-80¡ã C. for 5 hours. The reaction mixture was washed with a small quantity of ether, dissolved in methanol (200 ml) and water (60 ml). To the mixture, sodium borohydride (5.7 g, 0.15 mol) was added portionwise over the internal temperature range 0¡ã to 20¡ã C. After stirring overnight at room temperature, the mixture was evaporated in vacuo, water added and extracted with benzene. The benzene layer was dried over anhydrous potassium carbonate and evaporated in vacuo. The resulting residue was purified by alumina column chromatography (eluted successively with petroleum ether, benzene and chloroform) and distilled, bp. 100¡ã-103¡ã C./0.9 mmHg, to afford the Compound No. 14 (1.6 g, 28.4percent) as a colorless oil.

253-72-5,1,6-Naphthyridinebelongs to naphthyridine compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Patent; Nippon Kayaku Kabushiki Kaisha; US4308273; (1981); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0157-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 5-methoxypyridine-3-amine (25 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg), and cesium carbonate (33 mg) in 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 6-chloro-N-(5-methoxypyridin-3-yl)-1,5-naphthyridine-3-amine (5.4 mg). MS m/z (M+H): 287.

1309774-03-5, The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); 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.91870-15-4,2,5-Dichloro-1,8-naphthyridine,as a common compound, the synthetic route is as follows.,91870-15-4

Example 2 Preparation of 5-chloro-2-phenyl-1,8-naphthyridine 19.7 mg (0.028 mmol) of bis(triphenylphosphine)palladium(II) chloride are added to a suspension of 279 mg (1.40 mmol) of 2,5-dichloro-1,8-naphthyridine, 171 mg (1.40 mmol) of benzeneboronic acid and 141 mg (1.68 mmol) of sodium hydrogencarbonate in 2.8 ml of DMF and 1.4 ml of water, and the mixture is heated to 80¡ã C. under nitrogen. The reaction mixture is stirred at this temperature for 23 hours. The reaction mixture is evaporated and chromatographed on a silica-gel column with ethyl acetate/petroleum ether as eluent: 5-chloro-2-phenyl-1,8-naphthyridine as colourless solid; MS (EI) 240 [M]+; 1H-NMR (CDCl3, 300 MHz): delta [ppm]=9.02 (d, J=4.7 Hz, 1H), 8.65 (d, J=8.7, 1H), 8.35-8.30 (m, 2H), 8.11 (d, J=8.7, 1H), 7.57-7.52 (m, 3H).

91870-15-4 2,5-Dichloro-1,8-naphthyridine 15588316, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK PATENT GMBH; Dorsch, Dieter; Sirrenberg, Christian; Mueller, Thomas J.J.; Merkul, Eugen; Karapetyan, Gnuni Amatunu; US2013/310391; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,7-Naphthyridin-2(1H)-one, cas is 54920-82-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

54920-82-0, Example 29 7-benzyl-5,6,7,8-tetrahydro-1,7-naphthyridine-2(1H)-one Ethanol (20 mL) and benzyl bromide (0.8 mL) were added to 1,7-naphthyridine-2(1H)-one (CAS registration No: 54920-82-0) (900 mg), and the mixture was heated and stirred at 80¡ãC for 18 hours. The mixture was cooled to 0¡ãC, and then sodium borohydride (1100 mg) was added to the mixture. The mixture was stirred at 0¡ãC for 10 minutes, then hydrochloric acid was added thereto, and the mixture was stirred for 90 minutes at room temperature, followed by neutralization with sodium hydroxide. Then, ethyl acetate was added to the mixture, and the organic layer was extracted. The organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and a solvent was removed by evaporation under reduced pressure. Thereafter, the resulting solid was washed with ethyl acetate to obtain the title compound (900 mg) having the following physical property values. 1H-NMR (CD3OD): delta 2.66, 2.80, 3.45, 3.75, 6.40, 7.29-7.44.

With the rapid development of chemical substances, we look forward to future research findings about 1,7-Naphthyridin-2(1H)-one

Reference£º
Patent; Ono Pharmaceutical Co., Ltd.; INUKAI, Takayuki; TAKEUCHI, Jun; YASUHIRO, Tomoko; (50 pag.)EP3239147; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (31.83 mg, 163.56 umol, 2.00 eq), 6-[4-(4-methylpiperazin-l-yl)-l-piperidyl]-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrazolo[l,5-a]pyrimidine (74.19 mg, 81.78 umol, 1.00 eq), Pd(dppf)Cl2 (11.97 mg, 16.36 umol, 0.20 eq), K2CO3 (33.91 mg, 245.34 umol, 3.00 eq) in dioxane/H20 (6.00 mL/0.9 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 120C for 1 hour under N2 atmosphere until LCMS showed the starting material was consumed completely. The reaction mixture was concentrated in vacuo to give a residue, which was purified by Biotage flash reversed-phase C-18 column chromatography eluting with MeOH/H20 (MeOH in water from 10% to 100%) to give the product of 2-methoxy-8-[6-[4-(4-methylpiperazin-l- yl)-l-piperidyl]pyrazolo[l,5-a]pyrimidin-3-yl]-l,5-naphthyridine (60) as a yellow solid. LC/MS (method 3): fe = 2.22 min, mlz (M + H)+ = 459.2; NMR (400 MHz, MeOD) delta 9.50 (s, 1H), 8.88 (d, J= 5.2 Hz, 1H), 8.77 (d, J= 2.4 Hz, 1H), 8.67 (d, J = 4.8 Hz, 1H), 8.41 (d, J = 2.8 Hz, 1H), 8.19 (d, J = 9.2 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 4.15 (s, 3H), 3.77-3.74 (m, 2H), 2.82-2.40 (m, 11H), 2.30 (s, 3H), 2.10-2.07 (m, 2H), 1.80-1.69 (m, 2H).

249889-68-7, As the rapid development of chemical substances, we look forward to future research findings about 249889-68-7

Reference£º
Patent; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; YU, Paul, B.; HUANG, Wenwei; SANDERSON, Philip, Edward; JIANG, Jian-kang; SHAMIM, Khalida; ZHENG, Wei; HUANG, Xiuli; TAWA, Gregory; LEE, Arthur; ALIMARDANOV, Asaf; HUANG, Junfeng; (357 pag.)WO2018/200855; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem