Category: 1569-16-0

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO216,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

To a solution of 2-methyl-l,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35mL) 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 wasconcentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) 5 7.07 (d, 1H, J= 7.38 Hz), 6.32 (d, 1H, J = 7.25 Hz), 3.36-3.33 (m, 2H), 2.76-2.65 (m, 2H), 2.22 (s, 3H),25 1.87-1.82 (m, 2H). M+H=149.15.

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

Reference£º
Patent; PHARMACIA CORPORATION; WO2005/51904; (2005); A2;,
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

Int-19B. Ethyl (?)-4-(2-(l,8-naphthyridin-2-yl)vinyl)-lH-pyrrole-2-carboxylate: 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. The precipitate was collected, triturated with DCM (2x) and the solid air-dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid. NMR (500 MHz, DMSO-c) delta 12.14 (br. s., 1H), (0504) 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 = (0505) 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]+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (117 pag.)WO2018/89360; (2018); A1;,
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 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)+.

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

Reference£º
Patent; SmithKline Beecham Corporation; EP1218005; (2004); B1;,
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

In a 25 mL microwave reaction tube,Adding 2-methylnaphthyridine,Salicylaldehyde 0.5 g (4 mmol) and 10 ml acetic anhydride,Forming an orange-red solution,At a controlled temperature of 130 ¡ã C,Microwave power 50W, microwave reaction 40min,With the thin layer of the reaction process to monitor;After the reaction,The solvent was concentrated under reduced pressure to remove acetic anhydride,Oil-like viscous liquid,Dissolved with hot ethanol,Then recrystallized from acetone,Precipitation of yellow powder,That is, 2- (2′-hydroxystyryl) naphthyridine probe reagent,Yield 35percent.

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

Reference£º
Patent; Guizhou University; Ceng, Xi; Ruan, Qin; Mou, Lan; Li, Zhao; Zhang, Hong; (29 pag.)CN106045996; (2016); A;,
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.

2-methyl-1,8-naphthyridine (288 mg, 2 mmol) and twice the equimolar amount of selenium dioxide (221.92 mg-443.84 mg, 2 mmol-4 mmol) was dissolved in 50 ml of 1,4-dioxane under nitrogen or without nitrogen protection at 80 ¡ã C to 130 ¡ã C for 8-16 hours. During the reaction, the silica gel plate was detected at any time until the basic reaction of 2-methyl-1,8-naphthyridine was completed and a new point was generated. After completion of the reaction, the reaction mixture was suspended, purified on silica gel column with dichloromethane to obtain 1,8-naphthyridine-2-aldehyde., 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; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY, CHINESE ACADEMY OF SCIENCES; FU, WENFU; ZHAO, CHUNCHAO; (14 pag.)CN104974181; (2017); B;,
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 solution of 2-Methyl-l ,8-naphthyridine (0.037 g, 0.257 mmol), Intermediate 25 (0.100 g, 0.257 mmol) and 4-methylbenzenesulfonamide (0.044 g, 0.257 mmol) in toluene (0.555 mL) was stirred at 110 C for 14 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was purified by preparative HPLC (Phenomenex Luna AXIA 5u21.2xl00 mm, 10 min gradient, 15 min run, 10% to 100% Solvent B = 90% MeOH-10% H2O-0.1%TFA, Solvent A = 10% MeOH-90% H2O-0.1%TFA) to afford TFA salts of IB and IE, respectively. These salts were individually dissolved in MeOH (1.000 mL) and 250 mg Dianion WA21J resin was added. After stirring at room temperarture for 1 h, the resin was removed by filtration and washed well with MeOH. The filtrates were concentrated in vacuo to afford IB (25.8 mg, 20%) as an orange-brown oil and IE (32.5 mg, 19%) as a brown oil, respectively. IB: NMR (500MHz, CDCb) 59.06 (dd,J=4.1, 1.9 Hz, 1H), 8.16-8.05 (m, 2H), (0395) 7.92 (d,J= 16.0 Hz, 1H), 7.54 (d,J= 8.3 Hz, 1H), 7.39 (dd,J= 8.0, 4.1 Hz, 1H), 7.25 (d, J= 1.4 Hz, 1H), 7.13-7.04 (m, 3H), 6.98 – 6.86 (m, 2H), 6.32 (dd,J=8.8, 7.2 Hz, 1H), 4.17 – 4.05 (m, 3H), 4.02 – 3.95 (m, 1H), 3.88 (s, 3H), 3.64 – 3.55 (m, 1H), 3.34 – 3.25 (m, 1H), 3.05 – 2.92 (m, 2H), 1.20 (t, J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 515.1 [M+H]+ (0396) IE.: NMR (500MHz, CDCB) delta 9.04 (dd,J=4.1, 1.9 Hz, 1H), 8.07 (dt,J=8.0, 1.5 Hz, 2H), 7.95 (d, J= 8.3 Hz, 2H), 7.48 – 7.31 (m, 4H), 7.08 – 7.00 (m, 2H), 6.93 – 6.83 (m, 1H), 6.81 (d,J=1.7Hz, 1H), 6.52 (d,J=1.7Hz, 1H), 6.23 (dd,J=8.7, 7.3 Hz, 1H), 4.26 (t, J= 7.4 Hz, 1H), 4.07 (q, J= 7.1 Hz, 2H), 3.92 – 3.79 (m, 4H), 3.77 – 3.68 (m, 1H), 3.48 – 3.33 (m, 5H), 3.20 – 3.08 (m, 1H), 3.02 – 2.81 (m, 3H), 1.12 (t,J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 659.2 [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; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (95 pag.)WO2019/94319; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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]+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Methyl[1,8]-Naphthyridine, 1569-16-0

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

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; Nagarajan, Srinivasan R.; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; Yi, Yu; Huff, Renee M.; Desai, Bipinchandra N.; Devadas, Balekudru; Parikh, Mihir D.; Penning, Thomas; US2004/92538; (2004); 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

To a solution of 2-methyl-1,8-naphthyridine (6.024 g, 41.8 mmol) (from step 1) in anhydrous THF (140 mL) at -40 ¡ãC under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (88.0 mL) and the reaction mixture was stirred at -40 ¡ãC for 30 min to give a blood-red solution. After stirring for 30 min at – 40 ¡ãC, neat diethyl carbonate (5.60 mL) was added drop wise to above solution in 5 min and the reaction mixture was warmed up to 0 ¡ãC (ice-bath) and stirred at that temperature for 2 h to give a dark reddish-orange solution. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (60.0 mL) to give an orange-red solution and the THF was removed in vacuo to give an orange-red mixture. The resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4/MgSO4, filtered and evaporated in vacuo to afford a dark orange-red crystalline solid (8.65 g). The crude residue was purified by Silica-gel flash chromatography using a Varian SF-40-120 g Super Flash silica gel column and elution with 10-100percent ethyl acetate in n-heptane to afford the desired product as a yellow-orange crystalline solid (7.76 g, yield 85percent). LC-MS analysis of the solid shows the desired product’s mass: m/z 217 (M+H) and m/z 239 (M+Na); Calculated for C12H12N2O2: 216.23. 1H NMR (400 MHz, DMSO-d6): delta 1.21 (t, J = 7.0 Hz, 3H), 4.10 (q, 2H), 4.89 (s, 1H), 6.77 (d, J = 9.38 Hz, 1H), 7.14 (m, 1H), 7.46 (d, J = 9.36 Hz, 1H), 7.89 (d, 1H), 8.36 (d, 1H), 11.80 (brs, 1H, -OH). 1H NMR of the isolated product was superimposable with that of an authentic sample of the product.

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

Reference£º
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
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

The mixture of 2-methyl-l,8-naphthyridine (115 mg, 0.799 mmol), E6A (148 mg, 0.799 mmol), and 4-methylbenzenesulfonamide (137 mg, 0.799 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu Omicron18 30 chi 100 mm; 10 min gradient from 85percent A: 15percent B to 0percent A: 100percent B (A = 90percent H2O/10 percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E6B (170 mg, 68percent yield). LCMS (ES): m/z 312.2 [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; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem