Category: 1569-16-0

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

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,1569-16-0

In the second step, 2-methyl-1,8-naphthyridine (27 mmol, 3.8 g) was dissolved in diethyl ether (50 mL) under a nitrogen atmosphere, and then cooled to -78¡ã C., and added dropwise with stirring (0.5 h increments). (b) Diethyl ether solution (20mL) of CH3-Li (32mmol, 1.6M, purchased from JV of BAHL Technology, Inc.), and then warmed to room temperature (25¡ãC) and stirred for 12h. The reaction was quenched by adding 15mL of saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with chloroform three times. The organic layers were combined and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give an orange-red oil. KMnO4 (96 mmol, 15.2 g, purchased from Beijing Chemical Industry Plant) was added at room temperature. After stirring for 6 h at 25¡ã C., the mixture was suction filtered, and the filtrate was evaporated under reduced pressure to obtain a crude solid product, which was further purified by column chromatography (petroleum ether/ethyl acetate mixture with a volume ratio of 100/1). A compound (known compound) having the structure represented by the formula (1-1) is obtained,The yield was 75percent.

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

Reference£º
Patent; Chinese Academy Of Sciences Chemical Institute; Fan Qinghua; Ma Wenpeng; Chen Fei; He Yanmei; (51 pag.)CN105111208; (2018); B;,
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

To a mixture of 10percent palladium on carbon (0.369 g, 0.347 mmol) in MeOH (20 mL) under nitrogen in a 500 mL Parr reaction vessel was added 2-methyl-l,8-naphthyridine (0.500 g, 3.47 mmol). The reaction mixture was vacuum flushed with nitrogen (3x), then with hydrogen (3x) and vigorously shaken under hydrogen at 60 psi at -25 ¡ãC for 23 h. The reaction was filtered through a pad of Celite and thoroughly washed with MeOH. The filtrated was concentrated in vacuo to afford a mixture of the title compounds (506.1 mg) as a white solid. NMR indicated a mixture of two products in a ratio of 1 :0.18 which was used without further purification. LC-MS retention time = 1.70 min; m/z = (0434) 149.06 [M+H]+. (Column: Phenomenex Luna CI 8 50 x 2.0 mm 3 muiotaeta. Solvent A = 90percent Water : 10percent MeOH : 0.1percent TFA. Solvent B = 10percent Water : 90percent MeOH : 0.1percent TFA. Flow Rate = 0.8 mL/min. Start percent B = 0. Final percent B = 100. Gradient Time = 4 minutes, then a 1 minute hold at 100percent B. Oven temperature = 40 ¡ãC. Wavelength = 220 nm). Major product: NMR (400 MHz, DMSO-d6) delta 6.99 (d, J=7.3 Hz, 1H), 6.24 (d, J=7.0 Hz, 1H), 6.21 (br s, 1H), 3.26 – 3.19 (m, 2H), 2.59 (t, J=6.3 Hz, 2H), 2.16 (s, 3H), 1.74 (dt, J=l 1.7, 6.0 Hz, 2H). Minor product: NMR (400 MHz, DMSO-d6) delta 7.76 – 7.69 (m, 1H), 7.12 (d, J=7.0 Hz, 1H), 6.39 (dd, J=7.2, 4.9 Hz, 1H), 3.49 – 3.33 (m, 1H), 2.70 – 2.61 (m, 2H), 1.89 – 1.78 (m, 1H), 1.47 – 1.33 (m, 1H), 1.15 (d, J=6.3 Hz, 3H).

1569-16-0 is used more and more widely, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); 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: C8H14ClNO37,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

The mixture of 2-methyl-l,8-naphthyridine (51 mg, 0.352 mmol), E5B (69 mg, 0.352 mmol), and 4-methylbenzenesulfonamide (60 mg, 0.352 mmol) in DME (5 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu C18 30 x l00 mm; 10 min gradient from 85percent A: 15percent B to 0percent A: 100percent B (A = 90percent H2O/I O percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E5C (16 mg, 14percent). LCMS (ES): m/z 323.3 [M+H]+.

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
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

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

Step 1: 2-Chloromethyl-1,8-naphthyridine A solution of 2-methyl-1,8-naphthyridine (Chem. Pharm. Bull., 19, 1857 (1971)), N-chlorosuccinimide (1.1 equivalent), and a catalytic amount of benzoylperoxide in CCl4 were irradiated at reflux with a 225 watt lamp for 5 hours. After cooling, the solid was filtered and the filtrate evaporated to dryness. The crude residue was chromatographed to give the title product., 1569-16-0

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

Reference£º
Patent; Merck Frosst Canada Inc.; US5273980; (1993); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

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. After cooling to room temperature, the precipitate was collected by filtration, triturated with DCM (2x) and dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid which was used in the next step without further purification. NMR (500MHz, DMSO-cfe) delta 12.14 (br. s., 1H), 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= 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]+.

1569-16-0, The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

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., 1569-16-0

1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various fields.

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

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
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

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,1569-16-0

: A mixture of 2-methyl-1,8-naphthyridine (250 mg, 1.734 mmol), 1H-indazole-5-carbaldehyde (253 mg, 1.734 mmol) and 4-methylbenzenesulfonamide (297 mg, 1.734 mmol) in toluene (4 mL) was heated at 110 ¡ãC overnight. The reaction was cooled to rt and diluted with EtOAc (15 mL). The solid was collected via filtering and rinsed with EtOAc (2 x 2 mL) and dried in vacuum to afford Intermediate E2A (415 mg, 1.524 mmol, 88percent yield). The crude product was used in the next reaction without further purification. LCMS (ES): m/z 273.2 [M+H]+.

1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; MORALES, Christian L.; HIGGINS, Mendi A.; MULL, Eric; (318 pag.)WO2018/89357; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem