Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.,1260670-05-0

Step 1 To a stirred solution of intermediate D-7 (200 mg, 0.45 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (165 mg, 0.68 mmol) in THF (8 mL) was added LHMDS (1 M in THF, 1.13 mL, 1.13 mmol) at RT. The mixture was stirred at 45 C for 2 h, then an additional 1 eq. of LHMDS was added and the mixture was stirred at 45 C overnight. The mixture was diluted with saturated Nu0 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was rediluted with 5 mL of DCM and TFA (0.5 mL) was added. The resulting mixture was stirred at 25 C for 2 h, then neutralized with NaHC03, and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by prep-TLC (DCM: MeOH = 15 : 1) to afford compound L-1. MS for L-1 : m/e = 550 and 552 (M+l).

As the paragraph descriping shows that 1260670-05-0 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); A1;,
1,8-Naphthyridine – Wikipedia
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7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

0158-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (100 mg), 5-(2-morpholinoethoxyl)pyridine-3-amine (92 mg), tris(dibenzylideneacetone)dipalladium(0) (37 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (47 mg), and cesium carbonate (267 mg) in 1,4-dioxane (2 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-(2-morpholinoethoxyl)pyridin-3-yl)-1,5-naphthyridine-3-amine (5.4 mg). MS m/z (M+H): 386.

1309774-03-5, With the rapid development of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

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
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1,8-Diazanaphthalene, cas is 254-60-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Step C: 2-Chloro-3-cyclopropyl-[1,8]naphthyridine (4-5). A mixture of naphthyridine 4-4 (14 g, 77 mmol) and 100 mL POCl3 and 0.1 mL DMF was refluxed at 120 C. for 3 hr and concentrated. The residue was treated with 300 mL ice-water and solid K2CO3 until pH=9. The mixture was extracted with ethyl acetate (*3), washed with brine and dried over MgSO4. After solvent removal, the desired compound 4-5 was obtained as a yellowish solid. 1H NMR (400 MHz, CDCl3): delta 9.00 (q, 1H), 8.10 (q, 1H), 7.78 (s, 1H), 7.50 (q, 1H), 2.34 (m, 1H), 1.00 (m, 2H), 0.82 (m, 2H).

254-60-4, With the rapid development of chemical substances, we look forward to future research findings about 1,8-Diazanaphthalene

Reference£º
Patent; Merck & Co., Inc.; US6410526; (2002); B1;,
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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 solution of selenium dioxide (8.61 g, 77.56 mmol) in 1 ,4 dioxane (140 mL) with 0.5 mL of water was stirred at 100 ¡ãC for 5 min. The mixture was cooled down to 0 ¡ãC and 2-Methyl- 1 ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at 100 ¡ãC for 5 h. Completion of the reaction was monitored by TLC. The reaction mixture was filtered through celite bed, washed with EtOAc (50 mL) and concentrated. The resulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60 mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brown solid). 1H NMR (300 MHz, DMSO-d6): delta 10.18 (s, 1 H), 9.28-9.27 (m, 1 H), 8.74 (d, J = 8.1 Hz, 1 H), 8.63 (d, J = 8.1 Hz, 1 H), 8.1 1 (dd, J = 8.4, 1.2 Hz, 1 H), 7.83-7.79 (m, 1 H). LCMS: (Method B) 159.0 (M +H), Rt. 2.44 min, 91.59percent (Max). HPLC: (Method B) Rt 2.41 min, 87.86percent (Max).

1569-16-0, As the rapid development of chemical substances, we look forward to future research findings about 1569-16-0

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
1,8-Naphthyridine – Wikipedia
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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
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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
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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;,
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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