March 2021 | Page 33 of 57 | Heterocyclic Building Blocks-Naphthyridine

Downstream synthetic route of 7-Bromo-2-chloro-1,5-naphthyridine

1309774-03-5, 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.,1309774-03-5 ,7-Bromo-2-chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Bromo-2-chloro-1,5-naphthyridine, and cas is 1309774-03-5, its synthesis route is as follows.

0607-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (46 mg), 3-methyl-4-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propyl)morpholine (64 mg), sodium carbonate (40 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg), 1,4-dioxane (5 mL), and water (1 mL) was stirred at 80 C. for 5 hour in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)propyl)-3-methylmorpholine (77 mg). MS m/z (M+H): 372.

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

Some tips on 1309774-03-5

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 7-Bromo-2-chloro-1,5-naphthyridine, 1309774-03-5

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.

0022-1 Several drops of a 4 mol/L hydrogen chloride-1,4-dioxane solution (3 mL) and water were added to 7-bromo-2-chloro-1,5-naphthyridine (250 mg), followed by stirring at 100 C. overnight. The reaction mixture was cooled to room temperature, and water was added thereto. The solid matter was collected by filtration, and washed with a mixture solution of water and hexane-ethyl acetate (1:1), thereby obtaining 7-bromo-1,5-naphthyridin-2-ol (190 mg) as a grey solid. 1H-NMR (DMSO-d6) delta: 11.96 (1H, brs), 8.56 (1H, d, J=2.3 Hz), 7.93 (1H, d, J=9.9 Hz), 7.85 (1H, d, J=2.30 Hz), 6.79 (1H, d, J=9.9 Hz).

Some tips on 15944-34-0

15944-34-0, 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.,15944-34-0 ,7-Chloro-1,8-naphthyridin-2-ol, other downstream synthetic routes, hurry up and to see

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

Preparation B 7-methoxy-1H-[1,8]naphthyridin-2-one To a solution of 7-chloro-1H-[1,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 mL) was added NaOMe (25 wt % in MeOH, 161 mL). The resulting solution was stirred at reflux for 15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added. The phases were separated and the aq. layer was extracted with EA (8*80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid (5.22 g, 100% yield). 1H NMR (d6DMSO) delta: 11.96 (s, 1H); 7.96 (d, J=8.5 Hz, 1H); 7.81 (d, J=9.4 Hz, 1H); 6.63 (d, J=8.5 Hz, 1H); 6.34 (d, J=9.4 Hz, 1H); 3.90 (s, 3H).

Reference£º
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Share a compound : 7689-62-5

The chemical industry reduces the impact on the environment during synthesis,7689-62-5,2-Chloro-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

7689-62-5, 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. 2-Chloro-1,5-naphthyridine, cas is 7689-62-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A glass microwave reaction vessel was charged with 1-(trans-4-aminocyclohexyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.1050 g, 0.339 mmol), 2-chloro-1,5-naphthyridine (0.067 g, 0.407 mmol, 00358), and diisopropylethylamine (0.177 ml, 1.017 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (0.484 ml) and heated to 120 C. for 2 days. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, 100*50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 15 min. Fractions containing product were collected and concentrated. The product was taken up in DCM and loaded onto a Silicycle Si-carbonate cartridge and washed with DCM and MeOH to remove any salts to give the title compound (6.4 mg, 0.016 mmol, 4.7% yield). LCMS showed product peak at 1.434 min (m+1=402.0). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.09-1.24 (m, 4H) 1.37-1.53 (m, 2H) 1.94 (d, J=11.93 Hz, 2H) 2.39 (d, J=12.13 Hz, 2H) 2.68 (qd, J=12.91, 3.13 Hz, 2H) 2.97-3.09 (m, 1H) 4.08-4.24 (m, 1H) 4.47 (tt, J=12.32, 3.91 Hz, 1H) 6.85 (d, J=9.19 Hz, 1H) 7.45 (dd, J=8.41, 4.30 Hz, 1H) 7.91-7.96 (m, 2H) 7.97 (d, J=8.61 Hz, 1H) 8.03 (d, J=9.19 Hz, 1H) 8.60 (d, J=3.33 Hz, 1H)

The chemical industry reduces the impact on the environment during synthesis,7689-62-5,2-Chloro-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

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

The important role of 7689-62-5

7689-62-5, 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.,7689-62-5 ,2-Chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Chloro-1,5-naphthyridine, and cas is 7689-62-5, its synthesis route is as follows.

(3) N-(2-chloro-5-(l,5-naphthyridin-2-yl)-3-pyridinyl)-4- fluorobenzenesulfonamide.; To a 50 mL round-bottomed flask was added 2-chloro-l,5- naphthyridine (54 mg, 328 mumol), N-(2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (135 mg, 328 mumol), tetrakis(triphenylphosphine)palladium (38 mg, 33 mumol), sodium carbonate (70 mg, 656 mumol), dioxane (3 mL). The reaction mixture was stirred at 100 0C for 30 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (3 mL) and extracted with EtOAc (2 X 30 mL). The organic extract was washed with saturated NaCl (2 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 80% EtOAc/hexanes to give N-(2-chloro-5-(l,5-naphthyridin-2- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (78 mg, 57% yield) as a white solid. MS (ESI pos. ion) m/z calc’d for Cl9H12ClFN4O2S: 414.0; found 415.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 7.07 (s, 1 H) 7.16 (t, J=8.55 Hz, 2 H) 7.73 (dd, J=8.55, 4.17 Hz, 1 H) 7.88 (dd, J=8.92, 4.97 Hz, 2 H) 8.11 (d, J=8.77 Hz, 1 H) 8.49 (d, J=8.48 Hz, 1 H) 8.55 (d, J=8.77 Hz, 1 H) 8.83 (d, ./=2.19 Hz, 1 H) 8.94 (d, ./==2.19 Hz, 1 H) 9.03 (dd, J=4.09, 1.61 Hz, 1 H)

Reference£º
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

New learning discoveries about 1375301-90-8

1375301-90-8, 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-1,7-naphthyridin-8(7H)-one, cas is 1375301-90-8,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A mixture of compound E3 (2.0 g, 8.89 mmol), sodium methanolate (2.40 g, 44.4 mmol) and copper(I) iodide (846 mg, 4.44 mmol) in DMF (20 mL) was stirred at 100 C for 16 h under N2. Then mixture was concentrated to give crude E4 which was used in the next step without further purification.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; SCOTT, Jack, D.; (65 pag.)WO2016/40226; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Introduction of a new synthetic route about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid

100361-18-0, 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. 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolidine dimethanesulfonate (12. 5g), 2-chlorobenzaldehyde (lO. Og) and triethylamine (12.2g) were in turn introduced into a reaction vessel at room temperature. After stirring the mixture for about 0. 5h, 7- chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8- naphthyridine-3-carboxylic acid (10. Og) was introduced thereto. The resultant reaction mixture was stirred for about 15h at room temperature, cooled to 0~5&degC, and stirred for about 3h. The title compound in the form of solid was filtered, washed with acetonitrile, and dried to prepare 16.3g of the title compound (Yield: 90.0%). ‘H NMR (o, CDC13) : 8.74 (s, 1H), 8.66 (s, 1H), 7.96 (d, J=12. 4Hz, 1H), 7.84 (d, J=7. 3Hz, 1H), 7.29 (m, 2H), 7.16 (m, 1H), 4.59 (bs, 2H), 4.18 (m, 2H), 4.02 (m, 1H), 3.94 (s, 3H), 3.93 (m, 1H), 3.59 (m, 1H), 3.42 (m, 1H), 1.22 (m, 2H), 1.01 (m, 2H) Mass (FAB): 512 (M+H)

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2003/87100; (2003); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Extracurricular laboratory: Synthetic route of 254-79-5

254-79-5, 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.,254-79-5 ,1,5-Naphthyridine, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,5-Naphthyridine, and cas is 254-79-5, its synthesis route is as follows.

1,5-naphthyridine (111.6 g, 0.85 mol) was dissolved in acetic acid (1000 mL), sodium acetate (140.9 g, 1.72 mol) was added and heated to 80 C.A solution of bromine (153 g, 0.96 mol) in 150 mL was added dropwise thereto, maintaining the temperature of the reaction mixture at 80 C – 90 C, and the reaction was completed at 85 C for 3 h.After cooling, the reaction solution was spun and H2O (1000 mL) was added.The mixture was made alkaline with 50% aqueous sodium hydroxide solution, stirred for 30 min, suction filtered, and the filter cake was washed with water and dried.Crude product added to ethyl acetate (1600 mL)Heated to reflux for 3 h.After cooling to room temperature, filtration, the filter cake was washed with ethyl acetate and dried to give 3,7-dibromo-1,5-naphthyridine.The filtrate was spun dry to give a crude 3-bromo naphthyridine (84 g, white yellow solid, yield 47%).Purification by petroleum ether: ethyl acetate = 20:1 – 10:1 yielded pure 3-bromonaphthalene (67 g, white solid, yield 37%).

Reference£º
Patent; Suzhou Kangrun Pharmaceutical Co., Ltd.; Jin Haowen; Xu Weiliang; Xu Weizheng; (8 pag.)CN108658977; (2018); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The important role of 100491-29-0

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.

EXAMPLE 63 In 10 ml of conc. hydrochloric acid was suspended 500 mg of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and the resulting suspension was subjected to reaction under reflux for 1 hour. The reaction mixture was diluted with 10 ml of water, and the crystals thus deposited were collected by filtration, and then washed with 2 ml of water to obtain 450 mg (yield 97.1%) of 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid having a melting point of 238-242 C. Melting point: 242.5-243.5 C. (recrystallized from chloroform-ethanol (2:1 by volume)).

Reference£º
Patent; Toyama Chemical Co., Ltd.; US4704459; (1987); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Downstream synthetic route of 8-Chloro-3-methoxy-1,5-naphthyridine

952059-69-7, 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. 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Five 20 mL microwave vials were each charged with 4-aminophenol (0.700 mg, 33 mmol) and 3 equivalents of cesium carbonate in 6.0 ml of DMF. The mixture was stirred at RT for 10 minutes. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (1 g, 26 mmol), the reaction vessels were capped and irradiated at 150 C. for 15 min in the microwave, at which time the reaction was determined complete by LCMS. The mixture was allowed to cool to ambient temperature and material from the five vessels was combined. A deep brown solid crashed out with addition of water. Filtered solids, washed with water and dried overnight in the vacuum oven to afford 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as a brown solid. [0359] Alternatively, the title compound may be prepared by the following method: In a nitrogen purged sealed pressure vessel, dissolved 4-aminophenol (0.617 g, 5.65 mmol) in DMF (0.030 L). Cesium carbonate (3.68 g, 11.3 mmol) was added and the mixture was stirred at RT for 5 min. Added 8-chloro-3-methoxy-1,5-naphthyridine (1.00 g, 5.14 mmol), heated to 90 C., stirred for 17 h. The mixture was allowed to cool to RT and was concentrated. The crude material was triturated with methanol, filtered, washed with methanol followed by water, and air dried to yield 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as brown solid. MS [M+H]=268.1; Calc’d 267.3 for C15H13N3O2.

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