Heterocyclic Building Blocks-Naphthyridine

959558-28-2, 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. 4-Bromo-2,7-naphthyridin-1-amine, cas is 959558-28-2,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A solution of Bromo compound 6a (96 mg, 0.43 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL, 10.8 mmol, 30 equiv) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 3b (150 mg, 0.36 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 50 C and allowed to stir 12 h. The reaction was quenched by addition of NH4Cl (5 mL) at room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 15 was obtained by flash column chromatography. Yield = 49%.; TLC Rf = 0.1 (10 % MeOH/CH2Cl2). 1H NMR (500 MHz, DMSO-d6) delta 10.65 (s, 1H), 9.60 (s, 1H), 8.93 (s, 1H), 8.74 (d, J = 5.7 Hz, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.92 (s, 2H), 7.88 (d, J = 5.7 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 3.55 (s, 2H), 2.80 (s, 3H), 2.37 (s, 8H), 2.14 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.01, 162.28, 158.58, 152.20, 149.63, 148.92, 147.44, 140.37, 138.34, 137.81, 132.86, 131.74, 127.93, 127.77, 123.97, 118.86, 117.71, 117.37, 112.05, 101.07, 92.66, 90.47, 57.90, 55.19, 53.17, 46.19, 24.28; HRMS (ESI+): calcd. for C30H29F3N7O (MH+) 560.2380, found 560.2380

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 959558-28-2, 4-Bromo-2,7-naphthyridin-1-amine

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15944-34-0, 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-1,8-naphthyridin-2-ol, cas is 15944-34-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 300 mg (1.66 mmole) OF7-CHLORO-LH- [1, 8] naphthyridin-2-one (J. ORG. Chem. 1990, 55, 4744-4750) in 5 ML of anhydrous DMF was cooled to 0 C in an ice bath under a N2 atmosphere. A solution of 1.0 M lithium bis (trimethylsilyl) amide in THF (2.0 mL, 2.0 mmole) was added in a dropwise fashion. After stirring at 0 C for 5 min. , 381 mg (2.49 mmole) of 1-bromo-3-methoxypropane was added. The ice bath was removed, and the reaction mixture was stirred at room temperature for 5 min. An additional 5 ML of anhydrous DMF was added, and the heterogeneous mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with EtOAc, and washed with H20 (3x) and brine. The organic layer was dried over MGS04, filtered, and concentrated. Purification by flash column chromatography (SIO2, 40% EtOAc/hexanes gradient to 60% EtOAc/hexanes) gave 304 mg (72 %) of 7-chloro- 1-(3-methoxypropyl)-1H-[1,8]naphthyridin-2-one. MS : NEZ 253. 1,255. 1 (M+I)

The chemical industry reduces the impact on the environment during synthesis,15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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.

To a microwave vial (10-20 mL) was added (6- (3-methylisoxazol-5-yl) – [1, 2, 4] triazolo [4, 3-b] pyridazin-3 -yl) methanamine (1.00 g, 4.34 mmol) and 8-chloro-3-methoxy-l, 5-naphthyridine (1.10 g, 5.65 mmol) in 2-butanol (12 mL) . The suspension was stirred at 1200C under microwave irradiation for four hours . The mixture was concentrated and taken up in ammonia in methanol (2.0 M) then purified by MPLC chromatography (eluted with 0-10% methanol in dichloromethane) to yield the product as a tan solid. MS m/z = 389.0 [M+l] + . CaIc ‘d for Ci9Hi6N8O2: 388.1

The chemical industry reduces the impact on the environment during synthesis,952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
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.

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.

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
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

Name is 7-Chloro-1,8-naphthyridin-2-ol, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 15944-34-0, 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, 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

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

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.

Step 1. Ethyl 1- (2, 4-difluorophenyl)-6-fluoro-4-oxo-7- (piperazin-1-yl)-1, 4-dihydronaphthyridine-3- carboxylate: Ethyl 7-chloro-1- (2, 4-difluorophenyl)-6-fluoro-4-oxo-1, 4-dihydronaphthyridine- 3-carboxylate (766 mg, 2.0 mmol) and piperazine (430 mg, 5. 0 mmol, 2.5 equiv) were dissolved in 20 mL of pyridine and allowed to stir at room temperature for 24 h. The solvent was removed in vacuo, and the crude product was taken up in CH2C12, washed with 5% aq Na2CO3, then water. The organic layer was dried (Na2SO4), evaporated in vacuo, and the resulting white solid was purified on silica gel column using a linear gradient (100% CH2C12 to 10% MeOH in CH2C12) to give a white solid. ESI MS m/z 433 (M+H+), 887 (2M+Na+) ; IH NMR (400 MHz, CDC13) : 8 8. 94 (s, 1H, quinolone), 8.12 (d, J= 12. 5 Hz, 1H, quinolone), 7.39 (app dd, J= 13. 3 Hz, 7.04 Hz, 1H, Ph), 7.26 (s, 1H, Ph), 7.04 (app q, J= 15. 7, 8. 6 Hz, 1H, Ph), 4.36 (q, J= 7.0, 2H, Et), 3.50 (app t, J= 4.7 Hz, 4H, piperazine), 2.87 (app t, J= 4.7 Hz, 4H, piperazine), 1. 38 (t, J= 7.0 Hz, 3H, Et).

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; CUMBRE INC.; WO2005/70940; (2005); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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.

A SOLUTION OF AMINE 31 (612 MG, 1.57 MMOL) and triethylamine (0.7 mL, 5.0 MMOL) in ACETONITRILE (4 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4-dihydro-naphthpyridine- 3-carboxylic acid (222 mg, 0.787 MMOL) under nitrogen and the reaction mixture was allowed to stir for 12 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3 X 10 mL). The residue was allowed to dry for 15 min. The solid was collected, resuspended in methanol (5 mL) and the reaction mixture was treated with hydrazine (1 mL). After 5 min, the reaction mixture was warmed to reflux and the resulting mixture was allowed to stir for 1 h. The reaction mixture was concentrated in vacuo, diluted with water and the solids were collected by filtration. The off white product was washed with water (3 x 20 mL), allowed to dry overnight to afford the title compound 1 (40.4 mg, 13%). MS 391 (M+H).

The chemical industry reduces the impact on the environment during synthesis,100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, and cas is 96568-07-9, its synthesis route is as follows.

EXAMPLE 64 Ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazole-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 4-(1,2,3-triazol-1-yl)piperidine hydrochloride (225 mg, 1.2 mmol) and DBU (182 mg, 1.2 mmol) was added to a suspension of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100 C. for 5 hrs. The suspended solid was filtered and the filtrate was concentrated to dryness. The residue was triturated with water and separated solid was filtered, washed with water and dried to give 135 mg of desired product. m.p. 213-214 C.; 1 H NMR (CDCl3) delta: 8.48 (s, 1H), 8.11 (d, 1H), 7.72 (s, 1H), 7.60 (s, 1H), 4.60-4.85 (m, 3H), 4.29-4.40 (q, 2H), 3.43-3.54 (m, 1H), 3.21-3.35 (m, 2H), 2.10-2.36 (m, 4H), 1.36 (t, 3H), 0.95-1.23 (m, 4H).

96568-07-9, 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.,96568-07-9 ,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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.

0157-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 5-methoxypyridine-3-amine (25 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg), and cesium carbonate (33 mg) in 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 6-chloro-N-(5-methoxypyridin-3-yl)-1,5-naphthyridine-3-amine (5.4 mg). MS m/z (M+H): 287.

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

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

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.

In a sealed tube, a mixture of 7-bromo-2-chloro-1,5-naphthyridine 4b (2.50 g, 10.3 mmol) and 28% aqueous ammonia solution (60 mL) in dioxane (60 mL) was heated at 140 C for 24 h. Then, the reaction mixture was allowed to cool at room temperature and water was added. The aqueous layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtrated and the solvent was removed under reduced pressure. The crude mixture was purified by column chromatography on silica gel eluting with dichloromethane, then dichloromethane/ethanol 98:2 to give compound 5 as a white solid (1.95 g, 85%); Rf=0.39 (CH2Cl2/EtOH, 96:4); mp: 168-169 C; 1H NMR (400 MHz, [D6]DMSO): delta=8.57 (d, J=2.1 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.96 (d, J=9.1 Hz, 1H), 6.98 (br s, 2H), 6.04 (d, J=9.1 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO): delta= 159.1, 145.1, 144.2, 138.6, 137.7, 133.8, 119.6, 116.9; MS (ESI) m/z (%): 224.0 (100) [M+H]+, 226.1 (100) [M+H+2]+.

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

Reference£º
Article; Defaux, Julien; Antoine, Maud; Loge, Cedric; Le Borgne, Marc; Schuster, Tilmann; Seipelt, Irene; Aicher, Babette; Teifel, Michael; Guenther, Eckhard; Gerlach, Matthias; Marchand, Pascal; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3748 – 3752;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem