Month: March 2021

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.

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, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1569-16-0 ,2-Methyl[1,8]-Naphthyridine, other downstream synthetic routes, hurry up and to see

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

254-60-4, 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. 1,8-Diazanaphthalene, cas is 254-60-4,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A. A solution of [1,8]naphthyridine (0.2 mmol) and potassium amide (0.8 mmol) in liquid ammonia (20 mL) is stirred at -40 C. for 3 h. The solution is concentrated. Residue is partitioned between EtOAc and water. EtOAc layer is separated and washed successively with water and brine. EtOAc layer is dried over sodium sulfate, filtered and concentrated to give [1,8]naphthyridin-2-ylamine which is used as is for the next step.

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 1,8-Diazanaphthalene, 254-60-4

Reference£º
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, 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. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH. Ethyl 7-((benzo[d]thiazol-2-yl)thio)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (3) Yield: 86 %, M.P. = 184.7 C. HPLC: 99.6 % purity. FTIR (ATR, cm-1 ): 1736 (C=O, ester), 1624 (C=O, ketone), 1043, 806, 750. 1H-NMR (300 MHz, DMSO-d6): delta = 1.25 (3H, t, J= 7.05 Hz , -CH3), 4.22 (2H, q, J= 7.05 Hz , -CH2-), 6.96-7.08 (2H, m, phenyl H(3), H(5)), 7.54-7.59 (2H, m, benzothiazole H(5), H(6)), 7.60-7.69 (1H, m, phenyl H(6)), 7.96-8.00 (1H, s, benzothiazole H(4), H(7)), 8.40 (1H, d, J= 8.85 Hz, naphthyridine H(5)), 8.64 (1H, s, naphthyridine H(2).13C-NMR (75 MHz, DMSO-d6): delta = 14.60, 60.81, 105.14 (q, J= 23.5 Hz), 112.49 (d, J= 22.6 Hz), 113.04, 121.01 (d, J= 19.1 Hz), 121.77 (d, J= 2.9 Hz), 122.04, 123.26, 124.28 (d, J= 13.3 Hz), 126.65, 127.14, 131.69 (d, J= 10.3 Hz), 137.28, 146.16, 149.15 (d, J= 21.0 Hz), 149.62, 152.03, 152.98 (d, J= 253.5 Hz), 155.09 (d, J= 3.4 Hz), 157.97 (dd, J= 250.7 Hz- 13.4 Hz), 162.77 (dd, J= 248.1 Hz- 11.6 Hz), 163.80, 173.15. HRMS (m/z): [M+H]+ calcd for C24H14N3O3S2F3: 514.0501; found 514.0492.

The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, 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. 7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Example 0762 0762-1 60% sodium hydride (136 mg) was added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (300 mg), (4-methoxyphenyl)methanol, and N-methylpyrrolidone (12.3 mL) at a temperature of from 0 C. to 5 C., followed by stirring at room temperature for 2 hours in a nitrogen atmosphere. After water and ethyl acetate were added to the reaction mixture, the organic layer was washed sequentially with 0.01 mol/L hydrochloric acid and with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), thereby obtaining 7-bromo-2-((4-methoxybenzyl)oxy)-1,5-naphthyridine (204 mg) as a white solid. MS m/z (M+H): 345.

The chemical industry reduces the impact on the environment during synthesis,1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

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

Name is Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 100491-29-0, its synthesis route is as follows.

EXAMPLE 1 Ethyl 7-chloro-1-(2,4-difluoro-5-nitrophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate To 8 ml of conc. sulfuric acid was added 2.00 grams of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate. With ice cooling and stirring, to the solution was added 600 mg of potassium nitrate in portions. The solution was stirred at room temperature for 30 minutes to complete nitration. Then the reaction solution was poured into a stirred mixture of 150 ml of chloroform and 100 ml of ice water. After stirring at room temperature for 15 minutes, the reaction solution separated. The chloroform layer was dried over anhydrous magnesium sulfate and then concentrated in vacua. The precipitated crystals were dispersed in ethanol, collected by filtration and washed with ethanol and then with diisopropyl ether to give 2.08 g of the title compound.

100491-29-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,100491-29-0 ,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5910498; (1999); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7 its synthesis route is as follows.

Step 1: N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide In a screw cap test tube were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (281 mg, 1443 mumol), N-(5-aminopyrimidin-2-yl)benzamide (281 mg, 1312 mumol) and pyridinium p-toluenesulfonate (494 mg, 1968 mumol) in butan-2-ol (2623 mul, 1312 mumol) then heated at 100 C. The reaction turned black in a minute. After 1 h, the reaction mixture showed full conversion to product according to LCMS. The reaction mixture was diluted with CH2Cl2, neutralized with sat. NaHCO3. An emulsion was formed but the two layers eventually separated. The aqueous phase was extracted 3 times with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated under reduce pressure to give a tan solid. The solid was triturated with hexane, filtered, and dried under vacuo. Brown solid was collected. LCMS confirmed the presence of the product, N-(5-(7-methoxy-1,5-naphthyridin-4-ylamino)pyrimidin-2-yl)benzamide. MS Calcd for C20H16N6O2: [M]+=372. Found: [M+H]+=373.

952059-69-7, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,952059-69-7 ,8-Chloro-3-methoxy-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7 its synthesis route is as follows.

Example 13; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(6-methoxy-l,5-naphthyridin- 4~yloxy)phenyl] acetamide; A mixture of 4-chloro-6-methoxy-l,5-naphthyridine (0.08 g), JV-(I -ethyl-lH-pyrazol-4- yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide (0.113 g), 4-dimethylaminopyridine (0.151 g) and chlorobenzene (1 ml) was stirred and heated under argon to 140C for 14 hours. The resultant mixture was cooled to ambient temperature and partitioned between methylene chloride and 2N aqueous hydrochloric acid. The organic extract was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a solvent gradient from ethyl acetate to a 19:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound as a solid (0.018 g); 1H NMR Spectrum:5 (DMSOd6) 1.32 (t, 3H), 3.58 (s, 2H), 3.75 (s, 3H), 3.95 (s, 3H), 4.07 (q, 2H), 6.79 (m, IH), 6.91 (d, IH), 6.93 (d, IH), 7.29 (d, IH), 7.31 (d, IH), 7.41 (s, IH), 7.87 (s, IH), 8.28 (d, IH), 8.61 (d, IH), 10.01 (s, IH); Mass Spectrum: M+H+ 434.

249889-68-7, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,249889-68-7 ,8-Chloro-2-methoxy-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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.

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)+.

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; 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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,7-Naphthyridin-2(1H)-one, and cas is 54920-82-0, its synthesis route is as follows.

To a solution of lH-l,7-naphthyridin-2-one (1.6 g, 11.0 mmol) in MeOH (50 mL) was added BnBr (2.1 g, 12.1 mmol) at to 70 ¡ãC. The resulting mixture was stirred at 70 ¡ãC for 3 hrs and then cooled to 0 ¡ãC. To the cooled mixture was added NaBH4 (2.09 g, 55.0 mmol). The resulting mixture was slowly warmed to rt and stirred for 3 hrs at rt. The reaction was quenched with 6N HC1 (20 mL). The resulting mixture was stirred at rt for 2 hrs, then basified with 2 N NaOH to pH 10 and extracted with DCM (50 mL) twice. The combined organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by column (eluting with DCM: MeOH =40:1, v:v) to give 7-benzyl-l,5,6,8-tetrahydro-l,7-naphthyridin-2-one (700 mg) as a yellow solid.

54920-82-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,54920-82-0 ,1,7-Naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1260670-05-0, 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. 3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-bromo-8-chloro-1,7-naphthyridine (2.43g) in toluene (30 mL), EtOH (10 mL), and 10%Na 2CO 3 aq. (10 mL)pd (dppf) Cl 2. DCM (420 mg) was added. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.1g) was added dropwise under N 2 protection. The mixture was allowed to stir at 100C for 16h. The reaction was quenched by H 2O (50 mL)and extracted by EtOAc for 3 times. Organic layer was combined and washed with brine. The resulting solution was concentrated and purified by silicagel (eluting with hexane-EtOAc using a gradient from 8: 1 to 5: 1) to afford 8-chloro-3-vinyl-1,7-naphthyridine (1.1g)as a brown solid. 88%).

The chemical industry reduces the impact on the environment during synthesis,1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BETTA PHARMACEUTICALS CO., LTD; ZHANG, Yao; WANG, Yiqian; FU, Bang; CHEN, Jie; WANG, Jiabing; DING, Lieming; (43 pag.)WO2020/15716; (2020); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem