Month: September 2020

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.

0391-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (79 mg), bis(pinacolato)diboron (99 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (26 mg), potassium acetate (64 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-Iodo-3-propyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (113 mg), sodium carbonate (69 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (23 mg), and water (0.2 mL) were added thereto, followed by stirring at 80 C. for 3 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, NH silica), thereby obtaining 2-chloro-7-(3-propyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (53 mg). MS m/z (M+H): 384.

1309774-03-5, As the rapid development of chemical substances, we look forward to future research findings about 1309774-03-5

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.10261-82-2,1,5-Naphthyridin-2(1H)-one,as a common compound, the synthetic route is as follows.,10261-82-2

A 250 mL round bottomed flask charged with 1,5-naphthyridin-2(1H)-one (2.98 g, 20.37 mmol) and phosphorus oxychloride (40 ml, 437 mmol) was heated at 100 C. for 3 h. The reaction was cooled to room temperature and excess POCl3 was removed in vacuo. The residue was poured onto ice and neutralized with NaHCO3. The mixture was extracted with DCM (4*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (ISCO (80 gram)) eluting with EtOAc:DCM (0:1?1:4) to give 1.08 g (32%, 2 steps) of a light-yellow amorphous solid. ESI-MS 164.9, 166.9 [M+1].

As the paragraph descriping shows that 10261-82-2 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

A mixture of 7-chloro-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1 g, 5.53 mmol), 3-bromo-1 , 1- dimethoxypropane (1.1 g, 6.09 mmol) and K2CO3 (1.1 g, 8.31 mmol) in DMF (20 mL) was heated at 70C for 4 h. The mixture was then allowed to cool to room temperature, poured into H2O (30 mL) and extracted with EtOAc (30 mL x 3). The combined organic extracts were washed with H2O (50 mL x 2), brine (50 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 30% EtOAc/petroleum ether to give a yellow solid of 7-chloro-1-(3,3- dimethoxypropyl)-1 ,2-dihydro-1 ,8-naphthyridin-2-one 6a (1 g, 64%). TLC : Rf = 0.54 (silica gel, EtOAc/petroleum ether = 1 : 1 , v/v).

15944-34-0, As the rapid development of chemical substances, we look forward to future research findings about 15944-34-0

Reference£º
Patent; REDX PHARMA PLC; COOPER, Ian; LYONS, Amanda; (102 pag.)WO2017/137743; (2017); 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.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,952059-69-7

A 0.5 – 2 mL microwave vial was charged with 1- (4- (3- (aminomethyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) -2- fluorophenyl)pyrrolidin-2-one (0.0792 g, 0.243 mmol), 8-chloro- 3-methoxy-l, 5-naphthyridine (0.0590 g, 0.303 mmol), and butan- 2-ol (1.00 ml, 0.243 mmol), sealed, then placed in a Personal Chemistry Microwave for 4 hours at 1200C. The mixture was concentrated, then triturated with MeOH to give 1- (2-fluoro-4- (3- ( (7-methoxy-l, 5-naphthyridin-4-ylamino) methyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) phenyl)pyrrolidin-2-one as the hydrochloric salt .MS (ESI pos. ion) m/z: 485 (MH+). Calc’d exact mass for C25H2IFN8O2: 484.

952059-69-7 8-Chloro-3-methoxy-1,5-naphthyridine 59427340, anaphthyridine compound, is more and more widely used in various fields.

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

3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Method N B-9 Ex. 3 To a stirred solution of Intermediate B-9 (400 mg, 0.937 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (252 mg, 1.03 mmol) in THF (10 mL) was added LHMDS (1 M in THF, 3.28 mL, 3.28 mmol) at RT. The mixture was stirred at 45 C overnight, quenched with NH CI (sat.) and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The residue was treated with 5 mL of DCM and 0.5 mL of TFA and stirred at 25 C for 2 h. The mixture was neutralized with NaHC03 and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica column chromatography (PE: EtOAc = 1 : 1) to afford example 3. MS for example 3: m/e = 533 and 535 (M+l).

1260670-05-0, As the rapid development of chemical substances, we look forward to future research findings about 1260670-05-0

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,5-Naphthyridin-2(1H)-one, cas is 10261-82-2, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

To a solution of 1.2 g of 1,5-naphthyridin-2(1H)-one in 24 mL of N,N-dimethylformamide, 0.82 g of 60% sodium hydride was added at 60C, and the mixture was stirred at the same temperature for 20 minutes, and then stirred at 55 to 80C for 30 minutes. Thereto was added 1.3 mL of 2-bromomethyl-1,3-dioxolan at 60C, the temperature of the reaction mixture was increased to 100C over 4 hours, and to the reaction mixture, 2.3 g of potassium carbonate was added, and the mixture was stirred at the same temperature for 3 hours. After leaving overnight, 0.85 mL of 2-bromomethyl-1,3-dioxolan and 0.33 g of 60% sodium hydride were added thereto, and the mixture was stirred at 70 to 75C for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, water, sodium chloride and chloroform were then added thereto, and the organic layer was separated. The aqueous layer was extracted with chloroform. 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 chloroform:methanol = 49:1 to obtain 1.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one as a light yellow solid. 1H-NMR (CDCl3) delta: 3.82-3.94 (2H, m), 3.96-4.05 (2H, m), 4.52 (2H, d, J = 4.2 Hz), 5.22 (1H, t, J = 4.2 Hz), 6.94 (1H, d, J = 9.8 Hz), 7.45 (1H, dd, J = 8.6, 4.5 Hz), 7.90-7.98 (2H, m), 8.54 (1H, dd, J = 4.5, 1.2 Hz)

10261-82-2, As the rapid development of chemical substances, we look forward to future research findings about 10261-82-2

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

3-Bromo-1,5-naphthyridine, cas is 17965-71-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

To a solution of 3-bromo-l,5-naphthyridine (C-2) (4.181 g, 20.0 mmol, 1.0 eq ) in 1,4-dioxane (100 mL), tert-butylcarbamate (2.812 g, 24.0 mmol, 1.2 eq), cesium carbonate (9.132 g, 28.0 mmol, 1.4 eq), tris(benzylideneacetone)dipalladium (183 mg, 0.20 mmol, 0.01 eq) and Xantphos (347 mg, 0.60 mmol, 0.03 eq) were added. The mixture was heated at reflux for 16 h under an argon atmosphere. After the reaction mixture was cooled to RT, it was diluted with water (300 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2S04 and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (15 – 25%o ethyl acetate- petroether) to afford the desired product, tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) (4.047 g, 82.5% yield) as a yellow oil. ‘H NMR (300 MHz, DMSO-17965-71-8, As the rapid development of chemical substances, we look forward to future research findings about 17965-71-8

Reference£º
Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); A1;,
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, Example 7 Synthesis of boronic acid 7Reaction reagents and conditions: a. 1 ) NaH, THF, r.t.; 2) nBuLi, B(OiPr)3, -70C to 0C7.1 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 0C. After the mixture was stirred at room temperature for 30 min, the mixture was cooled below -60C 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 0C slowly in an ice bath. HC1 (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 x 120 mL) and EtOAc (100 mL) . The aqueous layer was adjusted to pH = 5-6 with HC1. The precipitate thus formed was collected by filtration and dried to give boronic acid 7 (3.5 g, 41%) a white solid.

As the rapid development of chemical substances, we look forward to future research findings about 72754-05-3

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; WO2013/29548; (2013); 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.,1569-16-0

a 2-Methyl-8-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,8-naphthyridine A mixture of 2-methyl-1,8-naphthyridine (J. Chem. Soc. (C) 1966, 315; 5.13 g, 35.58 mmole), 10percent Pd/C (1.14 g, 1.07 mmole), and absolute EtOH (70 mL) was deoxygenated through three evacuation/H2 purge cycles, then was stirred briskly under a balloon of H2. After 18.5 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, and the residue was reconcentrated from EtOAc to leave an off-white solid (5.25 g). A solution of the above material (5.25 g), di-tert-butyl dicarbonate (15.53 g, 71.16 mmole), and CH2Cl2 (10 mL) was concentrated on the rotavap to remove the solvent, and the oily residue was heated under N2 in an oil bath set at 55-60¡ã C. After 45 hr, the reaction was cooled to RT, and the residue was flash chromatographed on silica gel (40percent EtOAc/hexanes). The title compound (4.90 g, 55percent) was obtained as a light yellow solid: 1H NMR (300 MHz, CDCl3) delta7.27 (d, J=7.6 Hz, 1H), 6.81 (d, 7.6 Hz, 1H), 3.69 -3.79 (m, 2H), 2.65-2.75 (m, 2H), 2.48 (s, 3H), 1.83-1.98 (m, 2H), 1.52 (s, 9H), MS (ES) m/e 249 (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; SmithKline Beecham Corporation; US6495560; (2002); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,8-Diazanaphthalene, cas is 254-60-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Synthesis of 2-[1-(2-tert-butyl-6-chloro-5-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridine 20 ml of dimethylacetamide and 5 ml (17.8 mmoles) of diisopropylethylamine are added into a single-necked flask containing 1.5 g (6.84 mmoles) of 2-tert-butyl-4,6-dichloro-5-methyl-pyrimidine and 1.46 g (6.84 mmoles) of 2-piperidin-4-yl-[1,8]naphthyridine. This mixture is heated at 100 C. overnight. The next day 0.2 equivalent of naphthyridine is added and the mixture is heated for another 6 hours. The reaction mixture is returned to ambient temperature before concentrating to dryness. The residue obtained is taken up in a mixture of water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The collected organic phases are dried over magnesium sulphate then the solvent is evaporated off under reduced pressure (2 kPa). The residue is chromatographed on silica gel eluding with a gradient of heptane-ethyl acetate (70-30) to heptane-ethyl acetate (50-50). 1.77 g of expected product is obtained. TLC: Rf=0.50 [silica gel, eluent heptane-ethyl acetate (50-50). 1H-NMR (CDCl3): delta 1.37 (s, 9H, tert-butyl); 2.1 (m, 1H, cyclopropyl); 2.15 (m, 4H, N-CH2–CH–CH2); 2.27 (s, 3H, CH3); 3.1 and 4.05 (2m, 4H, CH2–N–CH2); 3.25 (m, 1H, N-CH2-CH2–CH2-CH2); [(7.48; 8.18; 9.12), 3m, 5H, naphthyridine]. MS: 396 (MH+).

254-60-4, As the rapid development of chemical substances, we look forward to future research findings about 254-60-4

Reference£º
Patent; Proskelia SAS; US2008/58348; (2008); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem