Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.254-60-4,1,8-Diazanaphthalene,as a common compound, the synthetic route is as follows.

A. A solution of [1,8]naphthyridine (0.2 mmol) and potassium amide (0.8 mmol) in liquid ammonia (20 mL) is stirred at -40 C. for 3 h. The solution is concentrated. Residue is partitioned between EtOAc and water. EtOAc layer is separated and washed successively with water and brine. EtOAc layer is dried over sodium sulfate, filtered and concentrated to give [1,8]naphthyridin-2-ylamine which is used as is for the next step., 254-60-4

The synthetic route of 254-60-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (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.100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.

EXAMPLE 1 Ethyl 7-chloro-1-(2,4-difluoro-5-nitrophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate To 8 ml of conc. sulfuric acid was added 2.00 grams of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate. With ice cooling and stirring, to the solution was added 600 mg of potassium nitrate in portions. The solution was stirred at room temperature for 30 minutes to complete nitration. Then the reaction solution was poured into a stirred mixture of 150 ml of chloroform and 100 ml of ice water. After stirring at room temperature for 15 minutes, the reaction solution separated. The chloroform layer was dried over anhydrous magnesium sulfate and then concentrated in vacua. The precipitated crystals were dispersed in ethanol, collected by filtration and washed with ethanol and then with diisopropyl ether to give 2.08 g of the title compound.

100491-29-0, As the paragraph descriping shows that 100491-29-0 is playing an increasingly important role.

Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5910498; (1999); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 63 In 10 ml of conc. hydrochloric acid was suspended 500 mg of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and the resulting suspension was subjected to reaction under reflux for 1 hour. The reaction mixture was diluted with 10 ml of water, and the crystals thus deposited were collected by filtration, and then washed with 2 ml of water to obtain 450 mg (yield 97.1%) of 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid having a melting point of 238-242 C. Melting point: 242.5-243.5 C. (recrystallized from chloroform-ethanol (2:1 by volume))., 100491-29-0

As the paragraph descriping shows that 100491-29-0 is playing an increasingly important role.

Reference£º
Patent; Toyama Chemical Co., Ltd.; US4704459; (1987); A;,
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.1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,1309774-03-5

0393-3 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (80 mg), 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (231 mg), sodium carbonate (87 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (23 mg), water (0.3 mL), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate-hexane), thereby obtaining 7-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-pyrazol-4-yl)-2-chloro-1,5-naphthyridine (76 mg). MS m/z (M+H): 389.

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

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.959558-28-2,4-Bromo-2,7-naphthyridin-1-amine,as a common compound, the synthetic route is as follows.,959558-28-2

A solution of Bromo compound 6a (100 mg, 0.45 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 2b (150 mg, 0.37 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 55 C and allowed to stir 12 h. The reaction was diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL), saturated NH4Cl (1 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 16 was obtained by flash column chromatography. Yield = 35%; TLC Rf = 0.1 (10 % MeOH/CH2Cl2) 1H NMR (500 MHz, DMSO-d6) delta 10.77 (s, 1H), 9.60 (s, 1H), 9.05 (d, J = 2.2 Hz, 1H), 9.00 (d, J = 2.0 Hz, 1H), 8.73 (d, J = 5.7 Hz, 1H), 8.54 (t, J = 2.1 Hz, 1H), 8.38 (s, 1H), 8.20 (s, 1H), 8.04 (d, J = 9.9 Hz, 1H), 7.96 (d, J = 5.7 Hz, 1H), 7.93 (s, 2H), 7.73 (s, 1H), 3.57 (s, 2H), 2.39 (s, 8H), 2.17 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.06, 158.62, 154.11, 152.24, 149.60, 148.90, 148.03, 140.47, 138.31, 137.37, 132.96, 131.83, 130.34, 128.86, 124.01, 120.21, 117.56, 112.05, 100.80, 90.37, 89.95, 57.87, 55.11, 53.02, 46.03; HRMS (ESI+): calcd. for C29H27F3N7O (MH+) 546.2224, found 546.2221

959558-28-2 4-Bromo-2,7-naphthyridin-1-amine 23727075, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

72754-05-3, 6-Bromo-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,72754-05-3

Boronic acid 7: To a solution of compound 6 (10 g, 44.44 mmol) in dry tetrahydrofuran (350 mL) was added sodium hydride (2 g, 66.66 mmol, 80% dispersion) at 0 C. After the mixture was stirred at room temperature for 30 min, the mixture was cooled below -60 C. in a dry ice/acetone bath, and n-butyllithium (70 mL, 112 mmol, 1.6 M in hexane) was added over 30 min. The mixture was kept stirring for another 30 min, then triisopropyl borate (40 mL, 177 mmol) was added dropwise. The reaction mixture was stirred for 10 min, and then warmed to 0 C. slowly in an ice bath. HCl (5 N) was added to the mixture to adjust pH=3-4, and the mixture was stirred for 20 min. Aq. NaOH was added to the mixture to adjust pH=10. After filtration, the organic layer was separated. The aqueous layer was extracted with a mixture of ethyl acetate/THF (4/1; 2¡Á120 mL) and EtOAc (100 mL). The aqueous layer was adjusted to pH=5-6 with HCl. The precipitate thus formed was collected by filtration and dried to give boronic acid 7 (3.5 g, 41%) as a white solid

The synthetic route of 72754-05-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (2014); A1;,
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

To a microwave vial (10-20 mL) was added (6- (3-methylisoxazol-5-yl) – [1, 2, 4] triazolo [4, 3-b] pyridazin-3 -yl) methanamine (1.00 g, 4.34 mmol) and 8-chloro-3-methoxy-l, 5-naphthyridine (1.10 g, 5.65 mmol) in 2-butanol (12 mL) . The suspension was stirred at 1200C under microwave irradiation for four hours . The mixture was concentrated and taken up in ammonia in methanol (2.0 M) then purified by MPLC chromatography (eluted with 0-10% methanol in dichloromethane) to yield the product as a tan solid. MS m/z = 389.0 [M+l] + . CaIc ‘d for Ci9Hi6N8O2: 388.1

The synthetic route of 952059-69-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

959558-28-2, 4-Bromo-2,7-naphthyridin-1-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,959558-28-2

A solution of Bromo compound 6a (96 mg, 0.43 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL, 10.8 mmol, 30 equiv) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 3b (150 mg, 0.36 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 50 C and allowed to stir 12 h. The reaction was quenched by addition of NH4Cl (5 mL) at room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 15 was obtained by flash column chromatography. Yield = 49%.; TLC Rf = 0.1 (10 % MeOH/CH2Cl2). 1H NMR (500 MHz, DMSO-d6) delta 10.65 (s, 1H), 9.60 (s, 1H), 8.93 (s, 1H), 8.74 (d, J = 5.7 Hz, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.92 (s, 2H), 7.88 (d, J = 5.7 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 3.55 (s, 2H), 2.80 (s, 3H), 2.37 (s, 8H), 2.14 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.01, 162.28, 158.58, 152.20, 149.63, 148.92, 147.44, 140.37, 138.34, 137.81, 132.86, 131.74, 127.93, 127.77, 123.97, 118.86, 117.71, 117.37, 112.05, 101.07, 92.66, 90.47, 57.90, 55.19, 53.17, 46.19, 24.28; HRMS (ESI+): calcd. for C30H29F3N7O (MH+) 560.2380, found 560.2380

As the paragraph descriping shows that 959558-28-2 is playing an increasingly important role.

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15944-34-0, 7-Chloro-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,15944-34-0

EXAMPLE 1; 7-Oxo-5 ,6,7,8-tetrahydro-ri,81naphthyridine-2-carboxylic acid methyl ester; 7-Chloro-lH-[l,8]naphthyridin-2-one (2 g, 11 mmol) was combined with triethylamine (1.1 g, 11 mmol) and bis (dppf) Pd (II) dichloride-dichloromethane complex (0.84 g, 1.0 mmol) in a 100 cc ss-reactor, purged with nitrogen and then with carbonmonoxide, pressurized to 500 psi, stirred and heated to 100 0C for 15 h. The solution was purged with nitrogen and concentrated then triturated in ethanol. The product was isolated as a solid, (2.1 g, 10 mmol, 92.9%). MS: APCI: M+l: 205.1 (Exact Mass: 204.2). 7-Oxo-5,6,7, 8-tetrahydro-[l,81naphthyridine-2-carboxylic acid7-Oxo-5,6,7,8-tetrahydro-[l,8]naphthyridine-2-carboxylic acid methyl ester (9.71 g, 47.1 mmol) and LiOH (3.9 g, 164 mmol) were stirred overnight in THF at room temperature. TLC showed disappearance of starting material so the reaction was concentrated and the residue was poured over ice water and neutralized withHCl then NH4OH. The solid that formed was collected via vacuum filtration and dried in vacuo then concentrated in toulene to remove water. The product was isolated as a white solid (8.56 g, 44.54 mmol, 94.5%). MS: APCI: M+l: 193.0 (Exact Mass: 192.17).

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

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90273; (2006); A2;,
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.72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

72754-05-3, 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one To a solution of 6-bromo-1,8-naphthyridin-2(1H)-one (0.1 g, 0.444 mmol) in DMF (2 mL) was added sodium hydride (0.021 g, 0.889 mmol) at 0 C. The reaction was stirred at 0 C. for 30 min, then SEM-Cl (0.118 mL, 0.667 mmol) was added. The reaction was stirred at room temperature overnight, then diluted with ammonium chloride solution, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether to give 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one (0.12 g, 76%). 1HNMR 400 MHz (CDCl3): 0.034 (s, 9H), 0.95-0.99 (m, 2H), 3.73-3.77 (m, 2H), 5.92 (s, 2H), 6.75-6.77 (m, 1H), 7.56-7.58 (m, 1H), 7.96-7.98 (m, 1H), 8.63-8.64 (m, 1H).

As the paragraph descriping shows that 72754-05-3 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem