Category: naphthyridine

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

Example 3.1 : 7-Bromo-[1 ,5]naphthyridin-2-ylamineIn a sealed reactor, 500 mg (1 .23 mmol, 1 eq) of 7-bromo-2-chloro-1 ,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C.1H-NMR (DMSO-d6, 400 MHz): delta = 8,57 (d, 1 H); 8,05 (d, 1 H); 7,96 (d, 1 H); 6,04 (d, 1 H); 6,98 (s, 2H) ppm.MS: m/z 225 (M+H+).

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

Reference£º
Patent; AeTERNA ZENTARIS GMBH; WO2011/64250; (2011); 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.

0384-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (32 mg), bis(pinacolato)diboron (50 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (11 mg), potassium acetate (26 mg), and 1,4-dioxane (1 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and 4-(3-(4-iodo-3-methyl-1H-pyrazol-1-yl)propyl)morpholine (44 mg), sodium carbonate (28 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (9 mg), and water (0.1 mL) were added thereto, followed by stirring at 80 C. for 2 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 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-methyl-1H-pyrazol-1-yl)propyl)morpholine (10 mg). MS m/z (M+H): 372., 1309774-03-5

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

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

55716-28-4, 8-Methoxy-1,7-naphthyridin-6-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,55716-28-4

B. 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0 C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3*500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101 C.

The synthetic route of 55716-28-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Novartis AG; US6136821; (2000); 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

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine 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)+.

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan F.; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; US2002/77321; (2002); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1309774-03-5

0031-1 A mixture solution of 7-bromo-2-chloro-1,5-naphthyridine (100 mg) in 1,4-dioxane (2 mL) and a 25% ammonia aqueous solution was stirred at 120 C. for 3 hours using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and a saturated sodium chloride aqueous solution and ethyl acetate were added thereto. The organic layer was collected by separation, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 7-bromo-1,5-naphthyridine-2-amine (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.0 (1H, d), 7.9 (1H, d), 7.0 (1H, d), 6.9 (1H, s). MS m/z (M+H): 224, 226.

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

17965-71-8, 3-Bromo-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,17965-71-8

Example 1.1.1 and Example 1.1.2: 3-Bromo-[1 ,5]naphthyridine-5-oxide and 3- bromo-1 ,5-naphthyridine-1 -oxide4.43 g (21.2 mmol, 1 eq) of 3-bromo-1 ,5-naphthyridine (W. Czuba, Recueil des Travaux Chimiques des Pays-Bas 1963, 82, 988-996) were introduced in 165 ml. of methylene chloride. 5.23 g (21.2 mmol, 1 eq) of mefa-chloroperbenzoic acid were then added portionwise at 0 C. The mixture was stirred at rt for 18 h. The mixture was washed with 1 M aqueous NaOH solution and water. Organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 3.08 g of 3-bromo-1 ,5- naphthyridine-5-oxide (pale yellow powder) with 64% yield and 1.00 g of 3-bromo-1 ,5- naphthyridine-1 -oxide (yellow powder) with 21 % yield.3-Bromo-[1 ,5]naphthyridine-5-oxideYield: 3.08 g (64 % of theory). m.p.: 148-149 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9,21 (d, 1 H); 9, 10 (d, 1 H); 8,75 (d, 1 H); 8,06 (d, 1 H); 7,80 (dd, 1 H) ppm. MS: m/z 226 (M+H+).3-Bromo-[1 ,5]naphthyridine-1 -oxide Yield: 1.00 g (21 % of theory), m.p.: 153-154 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9, 12 (d, 1 H); 9,03 (s, 1 H); 8,86 (d, 1 H); 8,36 (s, 1 H); 7,94 (dd, 1 H) ppm.MS: m/z 226 (M+H+).

The synthetic route of 17965-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AeTERNA ZENTARIS GMBH; WO2011/64250; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15944-34-0, 7-Chloro-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,15944-34-0

To a solution of 7-chloro-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1.80 g, 10.0 mmol) and 2- bromo-1 , 1-diethoxyethane (4.92 g, 25.0 mmol) in DMF (25 mL) was added Cs2C03 (4.90 g, 15.0 mmol) and the mixture heated at 70C under N2 overnight. The mixture was diluted with H2O (200 mL), extracted with EtOAc (100 mL x 3) and the combined organic extracts were washed with H2O (200 mL x 2), brine (100 mL) and concentrated under reduced pressure. The residue was purified by chromatography (EtOAc/petroleum ether, 1 :5 to 1 :2, v/v) to afford a white solid of 7-chloro-1-(2,2-diethoxyethyl)-1 ,2-dihydro-1 ,8-naphthyridin-2- one 5a (1.80 g, 61 %). TLC: Rf = 0.45 (silica gel, petroleum ether/EtOAc = 2 : 1 , v/v). 1 H NMR (Method E) (CDC ): delta ppm 7.78 (d, J = 8.0 Hz, 1 H), 7.61 (d, J = 9.6 Hz, 1 H), 7.15 (d, J = 8.0 Hz, 1 H), 6.72 (d, J = 9.6 Hz, 1 H), 5.10 (t, J = 5.6 Hz, 1 H), 4.67 (d, J = 5.6 Hz, 2H), 3.79 (m, 2H), 3.54 (m, 2H), 1.1 1 (t, J = 7.2 Hz, 6H).

The synthetic route of 15944-34-0 has been constantly updated, and we look forward to future research findings.

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.17965-71-8,3-Bromo-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

To 50 mL of chloroform, 5.00 g of 3-bromo-1,5-naphthyridin was dissolved, 6.40 g of m-chloroperbenzoic acid was added thereto, and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, a 5% aqueous sodium thiosulfate solution and chloroform were added, and the organic layer was separated, washed sequentially with a 5% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution and 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 silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of ethyl acetate:hexane = 1:1 to obtain 1.95 g of 3-bromo-1,5-naphthyridin-5-oxide as a light yellow solid. 1H-NMR (CDCl3) delta: 7.55 (1H, dd, J = 8.7, 6.0 Hz), 7.99 (1H, d, J = 8.7 Hz), 8.55 (1H, d, J = 6.0 Hz), 9.04 (1H, d, J = 2.3 Hz), 9.23 (1H, d, J = 2.3 Hz)

17965-71-8, 17965-71-8 3-Bromo-1,5-naphthyridine 12878818, anaphthyridine compound, is more and more widely used in various fields.

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

1260670-05-0, 3-Bromo-8-chloro-1,7-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2 – Synthesis of tert-butyl (R)-(4-(5-((3-bromo-l, 7-naphthyridin-8-yl)amino)-2- fluorophenyl)-2,4, 7, 7-tetramethyl-l, l-dioxido-l,2,5-thiadiazepan-6-ylidene)carbamate To a solution of 3-bromo-8-chloro-l,7-naphthyridine (205 mg, 0.840 mmol) and (R)-tert- butyl (4-(5-amino-2-fluorophenyl)-2,4,7,7-tetramethyl- 1 , 1 -dioxido- 1 ,2,5-thiadiazepan-6- ylidene) carbamate (300 mg, 0.70 mmol) in DMA (3 mL) was added KHMDS (2.45 mL, 2.45 mmol, 1.0 M in THF). The mixture was heated to 50 C and stirred for 2 h. The mixture was cooled and diluted with ethyl acetate. After separation, the organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with 0-5% MeOH in DCM, to afford the desired product.

1260670-05-0, 1260670-05-0 3-Bromo-8-chloro-1,7-naphthyridine 72213592, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; SCOTT, Jack, D.; LIU, Hong; PALANI, Anandan; WO2015/95104; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0392-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), morpholine (18 mL), tris (dibenzylideneacetone)dipalladium(0) (18 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg), sodium tert-butoxide (39 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 3 hours. 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), thereby obtaining 4-(6-chloro-1,5-naphthyridin-3-yl)morpholine (5.5 mg). MS m/z (M+H): 250.

1309774-03-5, 1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

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