Category: 1569-16-0

New learning discoveries about 1569-16-0

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

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

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

New learning discoveries about 1569-16-0

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

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.,1569-16-0

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine 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)+.

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

Reference£º
Patent; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan F.; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; US2002/77321; (2002); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

New learning discoveries about 1569-16-0

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

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.

To a solution of (R)-tert-butyl 3-(1,1-difluoro-4-iodobutyl)pyrrolidine-1-carboxylate (700 mg, 1.88 mmol) and 2-methyl-1,8-naphthyridine (407 mg, 2.82 mmol) in THF (12 mL) at 0¡ã C. was added LiHMDS (2.82 mL, 1M, 2.82 mmol). The reaction mixture was stirred at 0¡ã C. for 3 h, then quenched with saturated ammonium chloride solution (6 mL), diluted with water (15 mL) and extracted with EtOAc (30 mL¡Á2). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-TLC to give the desired product tert-butyl 3-(5-(1,8-naphthyridin-2-yl)pentyl)-3-fluoropyrrolidine-1-carboxylate as a light yellow solid (350 mg). Yield 48percent (ESI 388 (M+H)+).

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

Reference£º
Patent; Lazuli, Inc.; Harrison, Bryce A.; Bursavich, Matthew G.; Brewer, Mark; Gerasyuto, Aleksey I.; Hahn, Kristopher N.; Konze, Kyle D.; Lin, Fu-Yang; Lippa, Blaise S.; Lugovskoy, Alexey A.; Rogers, Bruce N.; Svensson, Mats A.; Troast, Dawn M.; (172 pag.)US2018/244648; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Brief introduction of 1569-16-0

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

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 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]+., 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

Application of Phthalazine

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

The naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine,cas is 1569-16-0, mainly used in chemical industry, its synthesis route is as follows.

2-Methyl-1,8-naphthyridine (1.1592 g, 8.0 mmol) and SeO2 (1.2452 g, 11.2 mmol) were added to 20 mL of 1,4-dioxane. The mixture were refluxed for 4 h in nitrogen atmosphere and filtered. The filtrate was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, ethyl acetate) (0.71 g, 56.6percent yield). Characterization of 1,8-naphthyridine-2-aldehyde: HRMS (EI) m/z: calcd for C9H7N2O [M+H]+, 159.0588; found, 159.0561. 1H NMR: (400 MHz; DMSO; TMS) 10.15 (s, 1H), 9.24-9.26 (m, 1H), 8.71 (d, 1H), 8.60-8.62 (m, 1H), 8.08 (d, 1H), 7.78-7.80 (m, 1H). 13C NMR (100 MHz, DMSO): 194.3, 155.8, 155.5, 155.0, 140.5, 138.3, 125.6, 124.9, 118.5.

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

Reference£º
Article; Liu, Xingjiang; Chen, Mingxing; Liu, Ziping; Yu, Mingming; Wei, Liuhe; Li, Zhanxian; Tetrahedron; vol. 70; 3; (2014); p. 658 – 663;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Application of 7-Bromo-2-chloro-1,5-naphthyridine

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

The naphthyridine compound, cas is 1569-16-0 name is 2-Methyl[1,8]-Naphthyridine, mainly used in chemical industry, its synthesis route is as follows.

The starting material tert-butyl 7-(2-hydroxyethyl)-2-methyl-3,4-dihydro-l,8- naphthyridine-l(2H)-carboxylate was prepared as follows: To a stirred solution of 2-methylnaphthyridine (2.0 g, 13.9 mmol) in THF (5 ml) was added at -78¡ãC MeLi 1.6M (7.2 ml, 41.7 mmol) over 5 minutes. The reaction mixture was left to stir at -780C for 2 hours, then at room temperature for 2 hours. Then a careful5 hydrolysis at 0¡ãC with water was followed by extraction of the aqueous layer with diethyl ether. The organic layer was dried and concentrated to give 2,7-dimethyl-l,2-dihydro-l,8- naphthyridine as a red oil (1.98 g, 90percent); Mass Spectrum [M+H]+ = 161; 1H NMR Spectrum (DMSO-d6) 1.20 (d, 3H), 2.14 (s, 3H), 4.41-4.49 (m, IH), 5.46 (ddd, IH), 6.17 (dd, IH), 6.20 (d, IH), 6.44 (s, IH), 6.90 (d, IH)., 1569-16-0

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/141473; (2007); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

New learning discoveries about 1569-16-0

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

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.,1569-16-0

STEP 2. SYNTHESIS OF (E)-1-ETHOXY-2- (1, 8-NAPHTHYRIDIN-2- YL) ethanol. To the product from step 1, (81.5 G, 0.57 mol) in anhydrous THF (1.9 L) at – 40 C under Ar gas was added lithium bis (trimethylsilyl) amide (1 M in THF, 1.2 L, 1.2 MOL). After stirring for 30 min at-40 C, DIETHYLCARBONATE (72.5 mL, 0.60 mol) was added. The temperature of the reaction mixture was warmed up to 0 C and stirred for 2 h. The reaction mixture was quenched into saturated aq. NH4CI (700 mL) and the THF removed under reduced pressure. The resulting mixture was extracted with EtOAc (3 x 700 mL). The organic layers were combined, washed with brine, dried over NA2SO4, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography using 50percent EtOAc/hexane to give a yellow solid (81.2 g, 0.38 mol, 66percent).APOS;H NMR (400 MHz, DMSO-d6) 8 1.22 (t, 3H), 4.11 (q, 2H), 4.89 (s, 1H), 6.78 (d, 1H), 7.15 (dd, 1H), 7.47 (d, 1H), 7.80 (d, 1H), 8.36 (d, 1H), 11.8 (bs, 1H). LC-MS (MH+) = 217.

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

Reference£º
Patent; PHARMACIA CORPORATION; WO2004/58761; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Application of 2-Chloro-10H-phenothiazine

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

The naphthyridine compound, it is a common heterocyclic compound, 1569-16-0,2-Methyl[1,8]-Naphthyridine,mainly used in chemical industry, its synthesis route is as follows.

The mixture of 2-methyl-l,8-naphthyridine (85 mg, 0.586 mmol), E25A (128 mg, 0.586 mmol), and 4-methylbenzenesulfonamide (100 mg, 0.586 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by reverse phase ISCO (26 g C18 30 min gradient from 100percent A: 0percent 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 E25B (18 mg, 5percent) as a minor byproduct. LCMS (ES): m/z 516.2 [M+H]+., 1569-16-0

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

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

Some tips on 1569-16-0

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

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.

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]+.

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

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

Analyzing the synthesis route of 1569-16-0

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

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.

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).

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; 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