Heterocyclic Building Blocks-Naphthyridine

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.

To 1,7-naphthyridine-2(1H)-one (CAS registration No.: 54920-82-0) (900 mg), ethanol (20 mL) and benzylbromide (0.8 mL) were added. The resulting mixture was heated and stirred at 80¡ãC for 18 hours. The resulting mixturewas cooled to 0¡ãC, and then sodium borohydride (1100 mg) was added thereto. The resulting product was stirred at0¡ãC for 10 minutes, and then hydrochloric acid was added thereto. The resulting mixture was stirred at room temperaturefor 90 minutes. The resulting product mixture was neutralized with sodium hydroxide, and then ethyl acetate was addedto extract the organic layer. The organic layer was extracted. The organic layer was washed with a saturated salinesolution, and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reducedpressure. Thereafter, the resulting solid was washed with ethyl acetate to obtain the title compound (900 mg) havingthe following physical property values.1H-NMR (CD3OD): delta 2.66, 2.80, 3.45, 3.75, 6.40, 7.29-7.44

As the paragraph descriping shows that 54920-82-0 is playing an increasingly important role.

Reference£º
Patent; ONO Pharmaceutical Co., Ltd.; INUKAI, Takayuki; TAKEUCHI, Jun; YASUHIRO, Tomoko; WOLF, Mark Allan; PAWAR, Vijay Dattaram; CHAKRABARTI, Anjan; CHITTIMALLA, Santhosh Kumar; (85 pag.)EP3067356; (2016); A1;,
1,8-Naphthyridine – Wikipedia
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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-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1.80 g, 10.0 mmol) and bromoacetaldehyde diethyl acetal (4.92 g, 25.0 mmol) in DMF (25 ml_) was added CS2CO3 (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).

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

Reference£º
Patent; REDX PHARMA PLC; COOPER, Ian; LYONS, Amanda; ORR, David; KIRKHAM, James; BLADES, Kevin; (267 pag.)WO2017/137744; (2017); A1;,
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249889-68-7, 8-Chloro-2-methoxy-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

81.i. N1-(6-methoxy-[1,5]naphthyridin-4-yl)-ethane-1,2-diamine A mixture of 8-chloro-2-methoxy-1,5-naphthyridine (1.71 g, 8.81 mmol) and ethylenediamine (1.18 mL, 2 eq.) was heated slowly to 80 C. over 1 h and subsequently up to 100 C. for 2 h. After cooling to rt, the yellow solution was taken in DCM and successively washed with NaHCO3. The aq. layer was back extracted with DCM (3 times) and the combined org. layers were concentrated to afford the title intermediate as a pale yellow oil (0.98 g, 51% yield). MS (ESI, m/z): 219.4 [M+H+].

The synthetic route of 249889-68-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Actelion Pharmaceuticals Ltd.; US2010/137290; (2010); 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.10261-82-2,1,5-Naphthyridin-2(1H)-one,as a common compound, the synthetic route is as follows.

To the compound 0001-1 (2.76 g), phosphorous oxychloride (8.3 mL) was added, and the mixture was stirred at 100C for 5 hours. The reaction solution which had been cooled to room temperature was added dropwise to a mixture of ethyl acetate (30 mL), water (30 mL), and sodium carbonate (9.57 g) in an ice-cooling bath over one hour. Further, water (10 mL) was added thereto, and sodium carbonate was added thereto until the pH reached 8.3. After stirring at room temperature for 10 minutes, the resulting mixture was subjected to liquid separation by the addition of ethyl acetate (270 mL) and water (200 mL). Further, the aqueous layer was extracted with ethyl acetate (200 mL) twice. The collected organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to obtain a compound 0001-2 (2.86 g) was obtained as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.05 (1H, dd), 8.50 (1H, dd, J=8.9), 8.41 (1H, ddd), 7.87, (1H, d), 7.86 (1H, m).

As the paragraph descriping shows that 10261-82-2 is playing an increasingly important role.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
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15992-83-3, 1,8-Naphthyridin-2-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 2-(1,8-naphthyridin-2-yl)phthalimide (8.6 g.), m.p. 250 C., by reacting 2-amino-1,8-naphthyridine (9.9 g.) with phthalic anhydride (10.2 g.) in dimethylformamide (75 cc.) at 150 C. for 1 hour 30 minutes.

15992-83-3 1,8-Naphthyridin-2-amine 4173048, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; Rhone-Poulenc S.A.; US4016274; (1977); A;,
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1,8-Naphthyridine | C8H6N2 – PubChem

15992-83-3, 1,8-Naphthyridin-2-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Part II- Synthesis of 2,6-Difluoro-N-[1,8]naphthyridin-2-ylbenzamide; [1,8]-Naphthyridin-2-ylamine (85 mg, 0.59 mmol) was dissolved in dichloromethane(2 mL) and pyridine (0.10 mL, 1.2 mmol). 2,6-Difluorobenzoyl chloride (0.068 mL, 0.76mmol) was then added and the reaction mixture was stirred at room temperature for 30 minutes. Next, the reaction mixture was diluted with ethyl acetate and washed with water followed bybrine. The resulting organic solution was purified by column chromatography (EtOAc/hexanes) to give 2,6-difluoro-N-[1,8]naphthyridin-2-ylbenzamide. Yield 35 mg (21 %).LCMS (ESI): calc. C1sH9FzN30 = 285; obs. M+H = 286.

The synthetic route of 15992-83-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; TOOGOOD, Peter, L.; HU, Xiao; WO2013/169864; (2013); A2;,
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

To a solution of 3-bromo-l,5-naphthyridine (C-2) (4.181 g, 20.0 mmol, 1.0 eq ) in 1,4-dioxane (100 mL), tert-butylcarbamate (2.812 g, 24.0 mmol, 1.2 eq), cesium carbonate (9.132 g, 28.0 mmol, 1.4 eq), tris(benzylideneacetone)dipalladium (183 mg, 0.20 mmol, 0.01 eq) and Xantphos (347 mg, 0.60 mmol, 0.03 eq) were added. The mixture was heated at reflux for 16 h under an argon atmosphere. After the reaction mixture was cooled to RT, it was diluted with water (300 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2S04 and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (15 – 25%o ethyl acetate- petroether) to afford the desired product, tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) (4.047 g, 82.5% yield) as a yellow oil. ‘H NMR (300 MHz, DMSO-Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); 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

To a stirred solution of 3-bromo-l,5-naphthyridine (C-2) (35.6 g, 170 mmol, 1.0 eq) in dichloromethane (300 mL) at 0C was added w-chloroperbenzoic acid (35.27 g, 204 mmol, 1.2 eq) in portions. The resulting mixture was stirred for lh at RT. The reaction was complete based on TLC analysis. The reaction mixture was washed with saturated Na2S03 solution and saturated NaHC03 solution sequentially, and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (1-5% MeOH-DCM) to afford the desired product 3-bromo-l,5-naphthyridine-5-oxide (C-3) (28.35 g, 74% yield). ‘H NMR (300 MHz, CDCl3-Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

197507-59-8, 1,6-Naphthyridine-2-carboxylic acid is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution OF 4- [ (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4-piperidinyl)- piperidine (50mg, 0. 12MMOL), 1, 6-naphthyridine-2-carboxylic acid (25mg, 0. 14MMOL), Et3N (44 mg, 0. 43MMOL) in DMF (3 mL, anhydrous) was added HATU (60mg, 0. 16MMOL) at room temperature. After 16 h the reaction mixture was poured into ice water, and the solid was collected by filtration. The solid was dissolved in CH2CI2, and dried over NA2SO4. CONCENTRATION in vacuo, and purification by preparative TLC (CH2CI2-MEOH, 9: 1) afforded the title compound as a light yellow powder. MS: 564 (M+).

As the paragraph descriping shows that 197507-59-8 is playing an increasingly important role.

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
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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

Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) (7.82 g, 0.02 mol) in 10% HCl (100 mL) was refluxed at 100 C for 3h. The reaction mixture was cooled down, diluted with 100 ml of H2O and adjusted to pH=7 by addition of ammonia (33%). The product was filtered off, dried and recrystallized from EtOH.

The synthetic route of 100491-29-0 has been constantly updated, and we look forward to future research findings.

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
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