Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.27225-00-9,2,7-Naphthyridin-1-amine,as a common compound, the synthetic route is as follows.,27225-00-9

4-Bromo-2,7-naphthyridin-1-ylamine32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25% aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

As the paragraph descriping shows that 27225-00-9 is playing an increasingly important role.

Reference£º
Patent; Merck Patent GmbH; Jonczyk, Alfred; Zenke, Frank T.; Amendt, Christiane; US2015/252041; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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,1569-16-0

: A mixture of 2-methyl-1,8-naphthyridine (250 mg, 1.734 mmol), 1H-indazole-5-carbaldehyde (253 mg, 1.734 mmol) and 4-methylbenzenesulfonamide (297 mg, 1.734 mmol) in toluene (4 mL) was heated at 110 ¡ãC overnight. The reaction was cooled to rt and diluted with EtOAc (15 mL). The solid was collected via filtering and rinsed with EtOAc (2 x 2 mL) and dried in vacuum to afford Intermediate E2A (415 mg, 1.524 mmol, 88percent yield). The crude product was used in the next reaction without further purification. LCMS (ES): m/z 273.2 [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; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; MORALES, Christian L.; HIGGINS, Mendi A.; MULL, Eric; (318 pag.)WO2018/89357; (2018); 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.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

To a solution of 7-chloro-l,8-naphthyridin-2(lH)-one (2.7 g, 15.2 mmol) (J.Org.Chem. 1990, 55, 4744-4750) in N,N-dimethylformamide (4OmL) under nitrogen at O0C was added sodium hydride (0.73 g, 18.3 mmol). The slurry was stirred for ten minutes and then (2- bromoethoxy)-t-butyl dimethylsilane (4.3 g, 18.3 mmol) was added. The mixture was heated at 8O0C for two hours then cooled to room temperature. The reaction mixture was quenched with water and the product extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with 20% acetone in n-hexane gave the product as an oil (3.2 g, 62%).MS CES): 338 (MH+) for C16H23N2SiClO21H NMR fDMSO-d): delta ppm -0.00 (s, 6H); 0.81 (s, 9H); 3.91 (t, 2H); 4.53 (t, 2H); 6.80 (d,IH); 7.45 (d, 1 H); 8.06 (d, IH); 8.29 (d, IH).

15944-34-0, 15944-34-0 7-Chloro-1,8-naphthyridin-2-ol 13302322, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71964; (2008); 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.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

EXAMPLESEXAMPLE l7-(4-Hydroxy-butoxy)-lH-[l,8]naphthyridin-2-one; To 1 liter (L) of n-methylpyrrolidinone was added 60% sodium hydride suspension (83.6g, 2.09moles). With external cooling to maintain 50C, 1,4-butanediol (3.39 moles) was added dropwise, causing offgassing. The mixture was stirred for 15 minutes at 60C, followed by addition of 7-Chloro-lH-[l,8]naphthyridin-2-one (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 146g, 0.813 moles) while stirring at 680C for 20 hours (h). To the mixture was added 5 liters of acetonitrile followed by filtration of a solid which was washed with a 50:50 mixture of acetonitrile and tetrahydrofuran. The solid was resuspended in 3 liters of tetrahydrofuran, to which was EPO added 3N HCl in methanol (290ml, 0.870 moles). After heating for 1 hour at 6O0C, the mixture was filtered thru celite, washed with 1 liter of tetrahydrofuran and concentrated to 500ml in volume. To the residue was added 1.5 liters of tetrahydrofuran, 1Og Darco activated charcoal, and 100ml Magnesol. After stirring at 40C for 30 minutes (min.), the mixture was filtered and washed with tetrahydrofuran and concentrated to 500ml in volume. To this residue was added 1 liter of acetonitrile followed by concentration of the mixture to 1 liter in volume. The resulting solid precipitate was filtered, washed with acetonitrile and ether, and dried at 50C giving 7-(4-Hydroxy-butoxy)-lH- [l,8]naphthyridin-2-one, 101g, (53% yield)., 15944-34-0

As the paragraph descriping shows that 15944-34-0 is playing an increasingly important role.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); 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.15936-10-4,2-Chloro-1,8-naphthyridine,as a common compound, the synthetic route is as follows.,15936-10-4

Example 82; 5-Methvl-6- (1, 8-naphthyridin-2-yl)-N [4-trifluoromethvl phenvl] pyrimidin-4-amine; To a mixture of Description 95 (200 mg, 0.7 mmol), Description 92 (115 mg, 0.7 mmol) and Pd (PPh3) 4 (80 mg, 0.07 mmol) in anhydrous 1, 4-dioxane (4 ml) was added hexamethylditin (0. 145 ml, 0.7 mmol). The mixture was heated at 190C for 15 min in a microwave reactor (Personal Chemistry-Smith synthesizer). The cooled reaction mixture was loaded directly onto a silica gel chromatography column and eluted with 2% MeOH + 0. 5% NH40H in DCM. The product was further purified by mass directed HPLC to give the title compound as a white solid (50 mg, 18%). 1H NMR (500 MHz, CDCl3) 2.70 (3 H, s), 6.94 (1 H, s), 7. 58 (1 H, dd, J8.1 and 4.2), 7.64 (2 H, d, J8.6), 7.84 (2 H, d, J8.6), 8. 25 (1 H, d, J8. 5), 8.29 (1 H, dd, J8. 1 and 1. 9), 8.38 (1 H, d, J 8. 4), 8. 81 (1 H, s), 9.20 (1 H, dd, J4.2 and 1.9) ; mlz (ES+) 382 (M+H+).

15936-10-4 2-Chloro-1,8-naphthyridine 5152838, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,100491-29-0

A. 7-([1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester [1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hexane and 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester were reacted and purified according to the procedure of Example 23.A to provide the title product as a solid, mp 181-183C (72% yield). 1H NMR (MeOH-d4): 8.57 (s, 1H), 7.96 (bd, J=12.4 Hz, 1H), 7.63 (m, 1H), 7.26 (m, 2H), 4.3 (vbm, 1H), 4.28 (q, J=7.0 Hz, 2H), 3.8 (vbm, 2H), 1.72 (m, 1H), 1.42 (s, 9H), 1.31 (t, J=7.0 Hz, 3H), 0.98 (m, 4H), 0.65 (m, 1H).

100491-29-0 Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 1268243, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; EP413455; (1991); A2;,
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.54920-82-0,1,7-Naphthyridin-2(1H)-one,as a common compound, the synthetic route is as follows.,54920-82-0

To a mixture of 1,7-naphthyridin-2(1H)-one (10 g, 68 mmol) in DMF (100 mL), BnBr (12.8 g, 75 mmol) was added. The mixture was stirred at 80 ¡ãC for 12 h. After cooling down, the reaction mixture was diluted with DCM/PE (100 mL/200 mL). The precipitate was filtered and dried to give 7-benzyl-2-oxo- 1 ,2-dthydro- 1 ,7-naphthyridin-7-ium Bromide (13.1 g, yield: 61percent) as a yellow solid. ESI-MS (M+H): 237.1.

The synthetic route of 54920-82-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); 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.1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,1309774-03-5

0386-2> A mixture of 7-bromo-2-chloro-1,5-naphthyridine (182 mg), bis(pinacolato)diboron (286 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (61 mg), potassium acetate (147 mg), and 1,4-dioxane (4 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 3-Ethyl-4-iodo-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (250 mg), sodium carbonate (158 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg), and water (0.4 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-ethyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (161 mg). MS m/z (M+H): 370.

The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

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.96568-07-9,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.,96568-07-9

EXAMPLE 4 Ethyl 1-cyclopropyl-6-fluoro-7-[3 (S)-(1,2,3-triazol-1-yl)pyrrolidin -1-yl]-1,4-dihydro-4-oxo-1,8naphthyridine-3-carboxylate Ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (250 mg, 0.8 mmol) was reacted with 350 mg (2 mmol) of 3(S)-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride in 8 ml of pyridine in the presence of 305 mg (2 mmol) of DBU at 80-90 C. for 6 h. The reaction was then stirred at r.t. for 4 days. The solvent was then evaporated under reduced pressure and to the residue, water was added and extracted with chloroform. The organic layer was dried and evaporated to dryness. The residue was then chromatographed over alumina (neutral, activity III) using chloroform as solvent to yield 80 mg (24%) of the desired product. 1 H NMR (CDCl3) delta: 8.48 (s, 1H), 8.05 (d, 1H), 7.76 (d, 1H), 7.71 (d, 1H), 5.46-5.32 (m, 1H), 4.46-4.26 (m, 4H), 4.15-4.0 (m, 2H), 3.56-3.42 (m, 1H), 2.71-2.57 (m, 2H), 1.4 (t, 3H), 1.26-0.95 (m, 4H).

As the paragraph descriping shows that 96568-07-9 is playing an increasingly important role.

Reference£º
Patent; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
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

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)+.

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

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