Heterocyclic Building Blocks-Naphthyridine

5,7-Dichloro-1,6-naphthyridine, cas is 337958-60-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A mixture of 5,7-dichloro-1,6-naphthyridine (4.0 g, 20 mmol) and Niodosuccinimide (9.0 g, 37 mmol) in acetic acid (100 mL) was heated at reflux for 12 h. The reaction mixture was concentrated under vacuum, and the residue was purified by column chromatography 20:1 petroleum ether:EtOAc to provide the title intermediate as ayellow solid (2.4 g, 37 % yield).

337958-60-8, As the rapid development of chemical substances, we look forward to future research findings about 337958-60-8

Reference£º
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (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.,15944-34-0

To a solution of 7-chloro-lH-[l,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 niL) was added NaOMe (25 wt% in MeOH, 161 rnL). 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 x 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, 1Eta); 7.96 (d, J = 8.5 Hz, IH); 7.81 (d, J = 9.4 Hz, IH); 6.63 (d, J = 8.5 Hz, IH); 6.34 (d, J = 9.4 Hz, IH); 3.90 (s, 3H).

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; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/116337; (2010); A1;,
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215523-34-5, 1,8-Naphthyridine-2-carboxylic acid is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

215523-34-5, General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM.

The synthetic route of 215523-34-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Talbot, Amelie; Maltais, Rene; Kenmogne, Lucie Carolle; Roy, Jenny; Poirier, Donald; Steroids; vol. 107; (2016); p. 55 – 64;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.215523-34-5,1,8-Naphthyridine-2-carboxylic acid,as a common compound, the synthetic route is as follows.,215523-34-5

600 mg (3.44 mmol) of 1,8-naphthyridine-2-carboxylic acid and 0.754 ml (10.3 mmol) of thionyl chloride were stirred in 15 ml of methanol at 60 C. for 6 h. The mixture was freed of the solvent under reduced pressure. Methyl tert-butyl ether was added to the residue and the mixture was freed of the solvent under reduced pressure. log P (neutral): 0.77; MH+: 189; 1H-NMR (400 MHz, CD3CN) delta ppm: 4.00 (s, 3H), 7.84 (dd, 1H), 8.27 (d, 1H), 8.70 (dd, 1H), 8.76 (d, 1H), 9.28 (m, 1H).

The synthetic route of 215523-34-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
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Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A. Method I: 560 mg (5mmol) of 1,4-diazabicyclo[2.2.2]octane and 890 mg (5.3 mmol) of 90% pure 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole are added to 1.9 g (5 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate in 20 ml of acetonitrile. The mixture is stirred at room temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 80 ml of water. The undissolved residue is filtered off with suction, washed with water and dried. Yield: 1.6 g (64% of theory) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylate, melting point: 173-176 C. (with decomposition)

100491-29-0, As the rapid development of chemical substances, we look forward to future research findings about 100491-29-0

Reference£º
Patent; Bayer Aktiengesellschaft; US5464796; (1995); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Chloro-1,8-naphthyridin-2-ol, cas is 15944-34-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis 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 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).

15944-34-0, As the rapid development of chemical substances, we look forward to future research findings about 15944-34-0

Reference£º
Patent; REDX PHARMA PLC; COOPER, Ian; LYONS, Amanda; (102 pag.)WO2017/137743; (2017); A1;,
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1,8-Naphthyridin-2-amine, cas is 15992-83-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Preparation of 5,7-dioxo-6-(1,8-naphthyridin-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (16.0 g.), m.p. 200 C., by reacting 2-amino-1,8-naphthyridine (8.65 g.) with 5,6-dihydro-1,4-dithiine-2,3-dicarboxylic acid anhydride (22.0 g.) [prepared according to the method of H. R. Schweizer, Helv. Chim. Acta, 52, 2229 (1969)] in diphenyl ether (70 cc.) at 150 C. for half an hour, in the presence of anhydrous acetic acid (0.4 cc.). Preparation of 5-hydroxy-6-(1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (13.0 g.), m.p. 260 C., by reacting sodium borohydride (2.15 g.) with 5,7-dioxo-6-(1,8-naphthyridin-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (18.0 g.) in anhydrous tetrahydrofuran (200 cc.) to which anhydrous methanol (80 cc.) has been added gradually, at a temperature not exceeding 40 C.

15992-83-3, As the rapid development of chemical substances, we look forward to future research findings about 15992-83-3

Reference£º
Patent; Rhone-Poulenc S.A.; US3948917; (1976); A;,
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2-Chloro-1,7-naphthyridine, cas is 35192-05-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Step B: Preparation of [N- (4-TERT-BUTYL-PHENYL)-2- ( [1, 7]] naphthyridin-2-ylamino)-benzamide A mixture of [2-AMINO-N- (4-TERT-BUTYL-PHENYL)-BENZAMIDE] (Step A, 163 mg, 0.61 mmol), [2-CHLORO- [1,] 7] naphthyridine [(100] mg, 0.61 [MMOL),] [PD2 (DBA)] 3 (6.0 mg, 0. [006] mmol), 2- dicyclohexyl [PHOSPHINO-2′- (N-N-DIMETHYAMINO)] biphenyl (6.0 mg, 0.015 mmol), and LiN (TMS) 2 (1 M solution in THF, 2.3 mL) was heated at [80 C] for 12 h in a sealed tube. The mixture was concentrated in vacuo and the crude material was purified with flash chromatography [(SI02,] [20%] EtOAc/hexane) and crystallization from EtOH to give the desired compound. MS [(ES+)] : [397.] 0 (M+H) [+.] Calc’d for [C25H24N4O-396.] 48.

35192-05-3, As the rapid development of chemical substances, we look forward to future research findings about 35192-05-3

Reference£º
Patent; AMGEN INC.; WO2004/5279; (2004); A2;,
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Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 96568-07-9, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

96568-07-9, Example 109 7-(4-chloro-2-isoindolinyl)-1-cyclopropyl-6-flurro-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid STR325 310 mg of 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4- oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 660 mg of 4-chloroisoindoline, 0.42 ml of triethylamine, and 5 ml of anhydrous chloroform were processed in the same manner as in Example 107 to produce 75 mg of 7-(4-chloro-2- isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8- naphthyridine-3-carboxylic acid. Melting point: above 300 C. 1 H-NMR (DMSO-d6) delta: 8.68 (1H, s, C2 –H), 8.06 (1H, d, C5 –H), 7.45-7.55 (3H, m, ARM-H), 5.3 (4H, br, s, 2 x–CH2 N–), 3.83 (1H. m, STR326 1.10-1.40 (4H, m, STR327

As the rapid development of chemical substances, we look forward to future research findings about 96568-07-9

Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5026856; (1991); A;,
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959558-28-2,959558-28-2, 4-Bromo-2,7-naphthyridin-1-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 32: Synthesis of 4-[2-(2-fluoro-phenyl)-[1 ,8]naphthyridin-4-yl]-[2,7]naphthyridin- 1- C/MS: 1.40, [M+H] 368

959558-28-2 4-Bromo-2,7-naphthyridin-1-amine 23727075, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK PATENT GMBH; JONCZYK, Alfred; DORSCH, Dieter; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2011/95196; (2011); A1;,
1,8-Naphthyridine – Wikipedia
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