Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1375301-90-8,3-Bromo-1,7-naphthyridin-8(7H)-one,as a common compound, the synthetic route is as follows.

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

The synthetic route of 1375301-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
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7689-62-5, 2-Chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A glass microwave reaction vessel was charged with 1-(trans-4-aminocyclohexyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.1050 g, 0.339 mmol), 2-chloro-1,5-naphthyridine (0.067 g, 0.407 mmol, 00358), and diisopropylethylamine (0.177 ml, 1.017 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (0.484 ml) and heated to 120 C. for 2 days. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, 100*50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 15 min. Fractions containing product were collected and concentrated. The product was taken up in DCM and loaded onto a Silicycle Si-carbonate cartridge and washed with DCM and MeOH to remove any salts to give the title compound (6.4 mg, 0.016 mmol, 4.7% yield). LCMS showed product peak at 1.434 min (m+1=402.0). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.09-1.24 (m, 4H) 1.37-1.53 (m, 2H) 1.94 (d, J=11.93 Hz, 2H) 2.39 (d, J=12.13 Hz, 2H) 2.68 (qd, J=12.91, 3.13 Hz, 2H) 2.97-3.09 (m, 1H) 4.08-4.24 (m, 1H) 4.47 (tt, J=12.32, 3.91 Hz, 1H) 6.85 (d, J=9.19 Hz, 1H) 7.45 (dd, J=8.41, 4.30 Hz, 1H) 7.91-7.96 (m, 2H) 7.97 (d, J=8.61 Hz, 1H) 8.03 (d, J=9.19 Hz, 1H) 8.60 (d, J=3.33 Hz, 1H)

As the paragraph descriping shows that 7689-62-5 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 8-Chloro-3-methoxy-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: (Method C5) Synthesis of N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine A pyrex reaction tube was charged with 8-chloro-3-methoxy-1,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol (80 mg, 0.26 mmol), cesium carbonate (249 mg, 0.76 mmol) and DMSO (2 mL). The tube was sealed and the reaction mixture was heated to 130 C. After 3.5 h, an aliquot was analyzed by LCMS, and the desired product was determined to be the major peak. The reaction mixture was diluted with DMSO and purified by Gilson HPLC {5-65% (0.1% TFA in CH3CN) in H2O over 20 min}. The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with DCM. The organic portion was dried with Na2SO4, filtered, and concentrated to afford material that was further purified by silica gel chromatography, 90/10/1 CH2Cl2/MeOH/NH4OH. This provided N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine as pure material. MS [M+H]=473.01.48 minutes. Calc’d for C28H20N6O2: 472.5.

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); 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

Example 3.1: 7-Bromo-[1,5]naphthyridin-2-ylamine [Show Image] In 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 Na2SO4, 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, 1H); 8,05 (d, 1H); 7,96 (d, 1H); 6,04 (d, 1H); 6,98 (s, 2H) ppm. MS: m/z 225 (M+H+).

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

Reference£º
Patent; Aeterna Zentaris GmbH; EP2332939; (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.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

Step 1 To a stirred solution of intermediate A-10 (1.43 g, 3.36 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (0.982 g, 4.03 mmol) in THF (34 ml) was added LHMDS in THF (11.8 ml, 11.8 mmol) at RT. The mixture was stirred at 45 C for 14 h, cooled, and diluted with dichloromethane (200 mL) and water (50 ml). The organic layers were collected, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (120 g of Si02> 0-100% EtOAc in hexane) to provide example 17. MS for example 17: m/e = 532 and 534 (M+l).

The synthetic route of 1260670-05-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (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.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

Starting compound 5 (9.6g, 39.4mmol, 1eq),Vinylboronic acid pinacol ester (6.68g, 43.4mmol, 1.1eq),Sodium carbonate (20.9g, 197.1mmol, 5eq) was added to the THF-water (4: 1,480mL, 50V) mixed solvent,After nitrogen substitution, tetratriphenylphosphine palladium (911.2mg, 0.79mmol, 0.02eq) was added,After nitrogen replacement again, stirring and heating to reflux,After 1.5h, TLC and LCMS analyzed a small amount of raw materials remaining.After the heat was turned off, after the system was concentrated, the residue was extracted three times with EA, and the organic phases were combined,It was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and column chromatography (EA in Hep 15%),The product compound 6 was obtained as a light yellow solid 5.9 g, and the yield was 76.1%.

As the paragraph descriping shows that 1260670-05-0 is playing an increasingly important role.

Reference£º
Patent; Shanghai Changsen Pharmaceutical Co., Ltd.; Wang Zhe; Zhang Jiyong; Zeng Zhihong; (105 pag.)CN111039942; (2020); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

253-72-5, 1,6-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the solution of 1,6-naphthyridine (830 mg, 6.38 mmol) in HOAc (5 mL), was added dropwise dibromine (612 mg, 3.83 mmol). The resulting suspension was stirred at 80¡ãC overnight. The reaction mixture was cooled to room temperature and added saturated NaHCC>3 aqueous solution to adjust pH to 8, extracted with dichloromethane (100 mL x 3). The combined organic layer was evaporated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1/1) to give the desired product (700 mg, 68percent) as a pale solid. H NMR (400 MHz, CDC13) delta 9.24 (d, / = 2.8 Hz, 1H), 9.21 (s, 1H), 9.02 (s, 1H), 8.34 (d, / = 8.0 Hz, 1H), 7.64 (dd, / = 8.0, 4.0 Hz, 1H).

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Reference£º
Patent; SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI; ZHANG, Xiaohu; ZHENG, Jiyue; MA, Haikuo; (184 pag.)WO2019/60860; (2019); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

2-methyl-1,8-naphthyridine (288 mg, 2 mmol) and twice the equimolar amount of selenium dioxide (221.92 mg-443.84 mg, 2 mmol-4 mmol) was dissolved in 50 ml of 1,4-dioxane under nitrogen or without nitrogen protection at 80 ¡ã C to 130 ¡ã C for 8-16 hours. During the reaction, the silica gel plate was detected at any time until the basic reaction of 2-methyl-1,8-naphthyridine was completed and a new point was generated. After completion of the reaction, the reaction mixture was suspended, purified on silica gel column with dichloromethane to obtain 1,8-naphthyridine-2-aldehyde.

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

Reference£º
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY, CHINESE ACADEMY OF SCIENCES; FU, WENFU; ZHAO, CHUNCHAO; (14 pag.)CN104974181; (2017); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

35192-05-3, 2-Chloro-1,7-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

As the paragraph descriping shows that 35192-05-3 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2004/5279; (2004); 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.100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

The compound obtained from the preparation example 10 (4.44 g), 1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8] naphthyridine-3-carboxylic acid (3.45 g), and triethylamine (2.6 in,) were added to acetonitrile (50 ml) in order and the reaction mixture was sitirred at 4550 C. for 4 hr. The precipitate was filtered and dried to obtain the desired compound (5.31 g, 77.6%). [00102] 1H-NMR(CDCl3, ppm) 0.80 (3H, s), 1.07 (2H, bs), 1.17 (3H, s), 1.24 (5H, bs), 1.26 (2H, bs), 1.41 (9H, s), 3.40 (2H, bs), 3.553.60 (5H, m), 4.054.32 (4H, m), 5.07 (1H, bs), 8.03 (1H, d, J=12.4 Hz), 8.71 (1H, s); [alpha]D=+9.77 (c=1.19, CHCl3, 25.0 C.).

The synthetic route of 100361-18-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dong Wha Pharm. Ind. Co., Ltd.; US6649763; (2003); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem