Month: October 2020

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Chloro-1,5-naphthyridine, and cas is 7689-62-5, its synthesis route is as follows.,7689-62-5

0001-3 A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was added dropwise to a mixture of 2-chloro-1,5-naphthyridine (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) at 85 C., and acetic acid (2 mL) was added thereto, followed by stirring at 85 C. for 3 hours. The reaction mixture was cooled to room temperature, and added dropwise to a 6 mol/L sodium hydroxide aqueous solution (60 mL) under ice-cooling. The solid matter was collected by filtration, suspended in methanol (5 mL), and subjected to an ultrasonic treatment. The solid matter was collected by filtration, and washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v % methanol aqueous solution (8 mL), the resultant product was subjected to an ultrasonic treatment, and the solid matter was collected by filtration, thereby obtaining 7-bromo-2-chloro-1,5-naphthyridine (3.33 g) as a pale yellow solid. MS m/z (M+H): 243.

7689-62-5 is used more and more widely, we look forward to future research findings about 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
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO251,mainly used in chemical industry, its synthesis route is as follows.,55716-28-4

B. 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0 C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3*500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101 C.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Methoxy-1,7-naphthyridin-6-amine,belong naphthyridine compound

Reference£º
Patent; Novartis AG; US6136821; (2000); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

6-Bromo-1,8-naphthyridin-2-ol, cas is 72754-05-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis 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).

With the rapid development of chemical substances, we look forward to future research findings about 6-Bromo-1,8-naphthyridin-2-ol

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

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

10g and 11.1gThe 1,5-naphthyridine derivative is dissolved in DMF.2.51 g of sodium hydride was added in portions on an ice bath.Add 5 minutes at room temperature after adding,After stirring for 2 hours at 50C,TLC showed that the raw material spots almost disappeared.Cool the reaction solution to ice bathIn an ice bath,Add 2.51g of sodium hydride,After stirring for 5 minutes,Add 4.5 ml acetyl chloride,There are a lot of white solids in the solution,After stirring for 3h at room temperature,Add 200ml of water to quench unreacted sodium hydride,Add 400ml of ethyl acetate to extractThe organic layer is washed three times,100ml each time.The organic layer is dry,concentrate,The concentrated oil was dissolved in 200 ml of THF.Join 37g TBAF,Stir at room temperature,The reaction gradually turned black.Stop the reaction after 30 minutes,Diluted the reaction with 100 ml of ethyl acetateWash 3 times,30ml each time.After the ethyl acetate layer is dry,concentrate,Get crude product.

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

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 7-Chloro-1,8-naphthyridin-2-ol, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 15944-34-0, its synthesis route is as follows.,15944-34-0

To a solution of 3.2 g of 7-chloro-1,8-naphthyridin-2(1H)-one in 32 mL of N,N-dimethylformamide, 3.7 g of potassium carbonate was added, and the mixture was stirred at 50 to 60C for 23 minutes, and then, thereto was added 2.2 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 60 to 78C for 25 minutes. Thereto were added 16 mL of N,N-dimethylformamide and 1.1 mL of 2-bromomethyl-1,3-dioxolan, the mixture was stirred at 90 to 95C for 2 hours 15 minutes, 3.7 g of potassium carbonate was added thereto, and the mixture was stirred for 20 minutes. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate = 1:1 to obtain 3.6 g of 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one as a yellow solid. 1H-NMR (CDCl3) delta: 3.86-3.96 (2H, m), 4.10-4.20 (2H, m), 4.63 (2H, t, J = 5.4 Hz), 5.60 (1H, t, J = 5.4 Hz), 6.75 (1H, d, J = 9.6 Hz), 7.17 (1H, d, J = 8.0 Hz), 7.62 (1H, d, J = 9.6 Hz), 7.79 (1H, d, J = 8.0 Hz)

With the complex challenges of chemical substances, we look forward to future research findings about 7-Chloro-1,8-naphthyridin-2-ol

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); 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 flask was charged with SeO2 (1.3 g, 11.7 mmol), 1,4-dioxane (20 mL) and a few drops of water. After the solution was refluxed for a few minutes, 2-methyl-1,8-naphthyridine (1 g, 6.9 mmol) was slowly added and the mixture turned red. The solution was then maintained at then continuing refluxed for another 3 h and during this time the red solution changed to brownish black. The hot solution was then filtered and the solvent was removed in vacuum. The resulting residue was dissolved in CH2Cl2, washed with water (3 x 30 mL), dried over Na2SO4 and concentrated under vacuum to give a brown solid. m.p. 65-68 ¡ãC. Yield: 60percent (0.67 g, 4.2 mmol). 1H-NMR (400 MHz, CDCl3) delta (ppm): 10.32 (s, 1H), 9.28-9.27 (m, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.32 (dd, J = 8.4 Hz, J = 1.2 Hz, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.63 (dd, J = 8.4 Hz, J = 4 Hz, 1H). 13C-NMR (100 MHz, CDCl3) delta: 193.5, 155.6, 155.4, 154.9, 138.8, 137.1, 125.2, 124.0, 118.3 ppm. Anal. Calcd for C9H6N2O: C 68.35; H 3.82, N 17.71. Found: C 68.21; H 3.56, N 17.85.

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
Article; Liu, Guiyan; Liu, Chengxin; Han, Fangwai; Wang, Zhongliang; Wang, Jianhui; Tetrahedron Letters; vol. 58; 8; (2017); p. 726 – 731;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,7-Chloro-1,8-naphthyridin-2-ol,15944-34-0,Molecular formula: C8H5ClN2O,mainly used in chemical industry, its synthesis route is as follows.,15944-34-0

To a solution of 7-chloro-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1.80 g, 10.0 mmol) and bromoacetaldehyde diethyl acetal (4.92 g, 25.0 mmol) in DMF (25 ml_) was added CS2CO3 (4.90 g, 15.0 mmol) and the mixture heated at 70C under N2 overnight. The mixture was diluted with H2O (200 ml_), extracted with EtOAc (100 ml_ x 3) and the combined organic extracts were washed with H2O (200 ml_ x 2), brine (100 ml_) and concentrated under reduced pressure. The residue was purified by chromatography (EtOAc/petroleum ether, 1 :5 to 1 :2, v/v) to afford a white solid of 7-chloro-1-(2,2-diethoxyethyl)-1 ,2-dihydro-1 ,8- naphthyridin-2-one 5a (1.80 g, 61 %). TLC: Rf = 0.45 (silica gel, petroleum ether/EtOAc = 2 : 1 , v/v). 1 H NMR (Method E) (CDC ): delta ppm 7.78 (d, J = 8.0 Hz, 1 H), 7.61 (d, J = 9.6 Hz, 1 H), 7.15 (d, J = 8.0 Hz, 1 H), 6.72 (d, J = 9.6 Hz, 1 H), 5.10 (t, J = 5.6 Hz, 1 H), 4.67 (d, J = 5.6 Hz, 2H), 3.79 (m, 2H), 3.54 (m, 2H), 1.1 1 (t, J = 7.2 Hz, 6H).

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Chloro-1,8-naphthyridin-2-ol,belong naphthyridine compound

Reference£º
Patent; REDX PHARMA PLC; COOPER, Ian; LYONS, Amanda; ORR, David; KIRKHAM, James; BLADES, Kevin; (267 pag.)WO2017/137744; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO345,mainly used in chemical industry, its synthesis route is as follows.,215523-34-5

To a suspension of 1,8-naphthyridine-2-carboxylic acid (2?g, 0.011?mol) in dry benzene (50?mL), was added oxalyl chloride (1.4?mL, 0.017?mol) drop wisely at 0?C. Then few drops of DMF were added and the reaction began immediately. It was then slowly brought to room temperature and heated at 65?C for 3?h until the gas evolution subsided. The solvent and excess oxalyl chloride was removed under reduced pressure to afford a light yellow residue of 1,8-naphthyridine-2-carbonyl chloride in almost quantitative yield which was directly used for the next step without further purification.

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

Reference£º
Article; Sarkar, Mithun; Pandey, Pragati; Bera, Jitendra K.; Inorganica Chimica Acta; vol. 486; (2019); p. 518 – 528;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,6-Naphthyridin-5(6H)-one, and cas is 23616-31-1, its synthesis route is as follows.,23616-31-1

[0622] A suspension of XI-3 (2.36 g, 15.7 mmol, 1 eq), N-bromosuccinimide (3.1 g, 17.3 mmol, 1 eq), and 50 mL of 1,2-dichloroethane was stirred at rt for 3.5 hrs. The mixture was filtered; the solids were washed successively with small amounts of chloroform, water, and diethyl ether, and then dried to leave XI-4 (0.8 g, 23percent yield). MS (ESI) m/z (M+H)+ 226.8.

With the complex challenges of chemical substances, we look forward to future research findings about 23616-31-1,belong naphthyridine compound

Reference£º
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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.

0421-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (48 mg), bis(pinacolato)diboron (58 mg), a 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride-dichloromethane complex (16 mg), potassium acetate (42 mg), and 1,4-dioxane (1.9 mL) was stirred at 100 C. for 2 hours. N-(4-bromopyridin-2-yl)acetamide (42 mg), sodium carbonate (45 mg), a bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (14 mg), 1,4-dioxane (0.3 mL), and water (0.19 mL)) were added to the reaction mixture, followed by stirring at 100 C. for 2 hours. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining N-(4-(6-chloro-1,5-naphthyridin-3-yl)pyridin-2-yl)acetamide (12.6 mg) as a pale brown solid. MS m/z (M+H): 299., 1309774-03-5

1309774-03-5 is used more and more widely, 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
1,8-Naphthyridine | C8H6N2 – PubChem