Heterocyclic Building Blocks-Naphthyridine

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

Example 7 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid. A mixture of tetrahydrofuran (450 cm3), water (50 cm3), methanesulfonic acid (127 cm3) and ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (United Kingdom Patent Publication No. GB 2,191,776) was heated at reflux for 1 hour, and then cooled to 25C. The resulting crystals were isolated, washed with tetrahydrofuran, and dried under vacuum to afford 41.3g (89%) of the above-titled compound: m.p. = 250C; (Found: C, 50.4; H, 1.7; Cl, 9.9; F, 16.0; N, 8.0. C15H6CIF3N2O3requires C, 50.8; H, 1.7; Cl, 10.0; F, 16.1; N, 7.9%); 1H NMR (300 MHz, d6-DMSO) delta 13.9 (s, 1H), 9.09 (s, 1H), 8.77 (d, J= 7.5 Hz, 1H), 7.86 (td, J= 5.9 and 8.8 Hz, 1H), 7.66 (ddd, J= 2.7, 9.0 and 11.8 Hz, 1H), 7.39 (tm, J= 8.6 Hz, 1H), 7.39 (tm, J= 8.6 Hz, 1H); numax(DRIFTS) cm-13130, 3060, 2947, 2885, 2821, 2723, 2637, 2594, 1734, 1641, 1623, 1579, 1544,1516.

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 Products Inc.; EP976749; (2000); A1;,
1,8-Naphthyridine – Wikipedia
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54920-82-0, 1,7-Naphthyridin-2(1H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

54920-82-0, Example 29 7-benzyl-5,6,7,8-tetrahydro-1,7-naphthyridine-2(1H)-one Ethanol (20 mL) and benzyl bromide (0.8 mL) were added to 1,7-naphthyridine-2(1H)-one (CAS registration No: 54920-82-0) (900 mg), and the mixture was heated and stirred at 80¡ãC for 18 hours. The mixture was cooled to 0¡ãC, and then sodium borohydride (1100 mg) was added to the mixture. The mixture was stirred at 0¡ãC for 10 minutes, then hydrochloric acid was added thereto, and the mixture was stirred for 90 minutes at room temperature, followed by neutralization with sodium hydroxide. Then, ethyl acetate was added to the mixture, and the organic layer was extracted. The organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and a solvent was removed by evaporation under reduced pressure. Thereafter, the resulting solid was washed with ethyl acetate to obtain the title compound (900 mg) having the following physical property values. 1H-NMR (CD3OD): delta 2.66, 2.80, 3.45, 3.75, 6.40, 7.29-7.44.

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

Reference£º
Patent; Ono Pharmaceutical Co., Ltd.; INUKAI, Takayuki; TAKEUCHI, Jun; YASUHIRO, Tomoko; (50 pag.)EP3239147; (2017); A1;,
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10261-82-2, 1,5-Naphthyridin-2(1H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,10261-82-2

To suspension of 1,5-naphthyridin-2(1H)-one (0.200 g, 1.368 mmol) in Pyridine (1 mL) was added slowly trifluoromethanesulfonic anhydride (0.050 mL, 0.298 mmol). After the addition, the reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated under high vacuum and residue diluted with water and extracted with EtOAc. EtOAc was washed with water, brine, dried over Na2SO4 and concentrated to give crude 1,5-naphthyridin-2-yl trifluoromethanesulfonate. To this crude 1,5-naphthyridin-2-yl trifluoromethanesulfonate (100 mg) in DMSO (0.5 mL) was added 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride, INTERMEDIATE 62, (0.05 g, 0.186 mmol) and N,N-diisopropylethylamine (0.032 mL, 0.186 mmol). The mixture was heated to 100 C. for 2 hours, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silical gel column eluting with 0-100% EtOAc/hexanes to give the title compound 7-(trans-3-((1,5-naphthyridin-2-yl)amino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.048 g, 0.133 mmol, 71.6% yield). m/z: 361.2; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.85 (s, 1H) 8.62 (dd, J=4.21, 1.27 Hz, 1H) 8.33 (s, 1H) 8.07 (d, J=9.00 Hz, 1H) 7.98 (d, J=8.22 Hz, 1H) 7.45 (dd, J=8.51, 4.21 Hz, 1H) 6.88 (d, J=9.00 Hz, 1H) 5.46 (d, J=4.50 Hz, 1H) 5.17-5.35 (m, 1H) 4.79 (dd, J=7.92, 3.62 Hz, 1H) 3.32-3.58 (m, 2H) 2.44 (tt, J=10.03, 3.08 Hz, 2H) 1.45 (s, 6H).

10261-82-2 1,5-Naphthyridin-2(1H)-one 589680, anaphthyridine compound, is more and more widely used in various fields.

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;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.254-79-5,1,5-Naphthyridine,as a common compound, the synthetic route is as follows.,254-79-5

To a stirred mixture of 1,5-naphthyridine (C-1) (50.0 g, 384 mmol, 1.0 eq) and sodium acetate(62.9 g, 768 mmol, 2.0 eq) in acetic acid (300 mL) at 80 C, a solution of bromine (67.5 g, 422 mmol, 1.1 eq) in acetic acid (80 mL) was added dropwise while keeping the reaction temperature at 80 C to 90 C. After stirring for 2 h at 80 C, the reaction was complete based on TLC analysis. The resulting mixture was cooled to RT and then filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0-30% ethyl acetate-petroether) to afford the desired product 3-bromo-l,5-naphthyridine (C-2) (36.5 g, 45 % yield ) as a pale yellow solid. :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
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2-Oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid, cas is 5175-14-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

5175-14-4, Step 3: 3-Bromo-l,8-naphthyridin-2-olA solution of bromine (3.78 g, 23.7 mmol) in pyridine (4 mL) and DMF (8 mL) was added to the product of Step 2 (450 mg, 2.37 mmol) and heated at 1050C for 1 hour. The reaction was cooled; H2O was added, and the mixture filtered. The filtrate was extracted with EtOAc (2x). The organic layers washed with brine and saturated NH4Cl(aq.) and dried over Na2SO4. The solvent was concentrated in vacuo, and the resulting gum was triturated with DCM, and filtered to give a brown solid (156 mg) as desired product. M+H = 224.9.

With the rapid development of chemical substances, we look forward to future research findings about 2-Oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

Reference£º
Patent; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2008/57209; (2008); A1;,
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4-Bromo-2,7-naphthyridin-1-amine, cas is 959558-28-2, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

959558-28-2, 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

With the rapid development of chemical substances, we look forward to future research findings about 4-Bromo-2,7-naphthyridin-1-amine

Reference£º
Patent; MERCK PATENT GMBH; JONCZYK, Alfred; DORSCH, Dieter; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2011/95196; (2011); A1;,
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131998-24-8, 5,7-Dichloro-1,8-naphthyridin-2-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,131998-24-8

. 5,7-dichloro-l,8-naphthyridin-2- amine (compound 1.2, 1.007 g, 4.70 mmoi) was dissolved in TFA (40 mL), then cooled 0 C. Sodium nitrite (1.623 g, 23.5 mmol) was added portion-wise at 0 C with stirring. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (20 niL), stirred for 5 minutes then carefully brought to pH =7 with NaOH (2 M). The resulting precipitated solids were filtered, washed with water and dried under reduced pressure to give compound 1.3 (864 mg, 85%). m/z (ES+) 215 (M+H)~.

As the paragraph descriping shows that 131998-24-8 is playing an increasingly important role.

Reference£º
Patent; 3-V BIOSCIENCES, INC.; WAGMAN, Allan S.; JOHNSON, Russell J.; CAI, Haiying; HU, Lily W.; (195 pag.)WO2017/31427; (2017); A1;,
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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.

0039-1 A solution of 7-bromo-2-chloro-1,5-naphthyridine (2.04 g), 5-cyclopentyl-1,3,4-thiadiazole-2-amine (1.41 g), and potassium carbonate (1.73 g) in dimethylsulfoxide (16 mL) was stirred at 130 C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, and the solid matter was collected by filtration, thereby obtaining N-(7-bromo-1,5-naphthyridin-2-yl)-5-cyclopentyl-1,3,4-thiadiazole-2-amine (1.92 g). 1H-NMR (DMSO-d6) delta: 12.20 (1H, s), 8.84 (1H, d, J=2.7 Hz), 8.56 (1H, d, J=2.7 Hz), 8.31 (1H, d, J=9.3 Hz), 7.51 (1H, d, J=9.3 Hz), 3.56-3.40 (1H, m), 2.22-2.08 (2H, m), 1.94-1.34 (6H, m). MS m/z (M+H): 376, 378.

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;,
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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.

A solution of Int-19A (0.300 g, 2.08 mmol), commercially available ethyl 4-formyl-lH- pyrrole-2-carboxylate (0.348 g, 2.08 mmol), and 4-methylbenzenesulfonamide (0.356 g, 2.08 mmol) in toluene (4.5 mL) was stirred at reflux for 21 h. After cooling to room temperature, the precipitate was collected by filtration, triturated with DCM (2x) and dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid which was used in the next step without further purification. NMR (500MHz, DMSO-cfe) delta 12.14 (br. s., 1H), 9.01 (dd, J = 4.3, 2.1 Hz, 1H), 8.41 – 8.28 (m, 2H), 7.82 (d, J = 16.2 Hz, 1H), 7.76 (d, J= 8.5 Hz, 1H), 7.52 (dd, J= 8.0, 4.1 Hz, 1H), 7.46 (s, 1H), 7.24 – 7.16 (m, 2H), 4.27 (q, J= 7.2 Hz, 2H), 1.31 (t, J= 7.0 Hz, 3H). HPLC retention time (Method 1): 1.973 mia; LCMS (ES): m/z 294.0 [M+H]+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (95 pag.)WO2019/94319; (2019); 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,952059-69-7

Method A B-9 Ex. 21 To a stirred solution of Intermediate B-9 (99.0 mg, 0.231 mmol) and 8-chloro-3-methoxy- 1 ,5-naphthyridine (30.0 mg, 0.154 mmol) in THF (4 ml) under nitrogen was added chloro[2- (dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-triisopropyl-l ,l ‘-biphenyl][2-(2- aminoethyl)phenyl]palladium(II) (24.6 mg, 0.0310 mmol) and sodium teri-butoxide (0.154 mL, 2 M) at RT. The mixture was stirred at 40 C for 15 h, cooled, filtered, and diluted with water (5 ml) and extracted with EtOAc (6 mL x 3). The organic layers were collected, dried with sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM (6 mL), treated with TFA (0.200 mL) and stirred at 18 C for 1 h. The mixture was quenched with aqueous sodium hydrogen carbonate (5 ml) and extracted with EtOAc (5 mL x 4). The combined organic extracts were washed with brine, dried (Na2S04), filtered and concentrated. The residue was purified by prep-HPLC (column 250 x 21.2 mm, 4 muiotaeta; mobile phases A = 0.075 % TFA water, B = MeCN; gradient 10-40% B, 11 min, 25 mL/min) to provide example 21. MS for example 21: m/e = 485 (M+l).

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

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
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