Month: November 2020

It is a common heterocyclic compound, the naphthyridine compound, Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 96568-07-9 its synthesis route is as follows.,96568-07-9

EXAMPLE 61 Ethyl (1’SR,2’SR,6’RS)-1-cyclopropyl-6-fluoro-1,4-dihydro-7-(2′-methylamino-8′-azabicyclo[4.3.0]non-4′-en-8′-yl)-4-oxo-1,8-naphthyridine-3-carboxylate STR201 The title compound is obtained by reacting ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate with the title compound from Example O, as described in Example 52. The hydrochloride is obtained by treating the product with a little dilute hydrochloric acid. Yield: 91% of theory. Rf =0.64 (methanol/dichloromethane/conc. ammonia 15:4:0.5).

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Patent; Bayer Aktiengesellschaft; US5556979; (1996); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 6-Bromo-1,8-naphthyridin-2-ol, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 72754-05-3, its synthesis route is as follows.,72754-05-3

Boronic acid 7: To a solution of compound 6 (10 g, 44.44 mmol) in dry tetrahydrofuran (350 mL) was added sodium hydride (2 g, 66.66 mmol, 80% dispersion) at 0 C. After the mixture was stirred at room temperature for 30 min, the mixture was cooled below -60 C. in a dry ice/acetone bath, and n-butyllithium (70 mL, 112 mmol, 1.6 M in hexane) was added over 30 min. The mixture was kept stirring for another 30 min, then triisopropyl borate (40 mL, 177 mmol) was added dropwise. The reaction mixture was stirred for 10 min, and then warmed to 0 C. slowly in an ice bath. HCl (5 N) was added to the mixture to adjust pH=3-4, and the mixture was stirred for 20 min. Aq. NaOH was added to the mixture to adjust pH=10. After filtration, the organic layer was separated. The aqueous layer was extracted with a mixture of ethyl acetate/THF (4/1; 2¡Á120 mL) and EtOAc (100 mL). The aqueous layer was adjusted to pH=5-6 with HCl. The precipitate thus formed was collected by filtration and dried to give boronic acid 7 (3.5 g, 41%) as a white solid

With the complex challenges of chemical substances, we look forward to future research findings about 6-Bromo-1,8-naphthyridin-2-ol

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2,5-Dichloro-1,8-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 91870-15-4, its synthesis route is as follows.,91870-15-4

Example 2 Preparation of 5-chloro-2-phenyl-1,8-naphthyridine 19.7 mg (0.028 mmol) of bis(triphenylphosphine)palladium(II) chloride are added to a suspension of 279 mg (1.40 mmol) of 2,5-dichloro-1,8-naphthyridine, 171 mg (1.40 mmol) of benzeneboronic acid and 141 mg (1.68 mmol) of sodium hydrogencarbonate in 2.8 ml of DMF and 1.4 ml of water, and the mixture is heated to 80¡ã C. under nitrogen. The reaction mixture is stirred at this temperature for 23 hours. The reaction mixture is evaporated and chromatographed on a silica-gel column with ethyl acetate/petroleum ether as eluent: 5-chloro-2-phenyl-1,8-naphthyridine as colourless solid; MS (EI) 240 [M]+; 1H-NMR (CDCl3, 300 MHz): delta [ppm]=9.02 (d, J=4.7 Hz, 1H), 8.65 (d, J=8.7, 1H), 8.35-8.30 (m, 2H), 8.11 (d, J=8.7, 1H), 7.57-7.52 (m, 3H).

With the complex challenges of chemical substances, we look forward to future research findings about 2,5-Dichloro-1,8-naphthyridine

Reference£º
Patent; MERCK PATENT GMBH; Dorsch, Dieter; Sirrenberg, Christian; Mueller, Thomas J.J.; Merkul, Eugen; Karapetyan, Gnuni Amatunu; US2013/310391; (2013); 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.

Example 2a: Synthesis of tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) C-2 D-12 [00315] 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% 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. lR NMR (300 MHz, DMSO- 6) delta: 10.02 (bs, 1H), 8.94 (s, 1H), 8.87 (m, 1H), 8.47 (s, 1H), 8.28 (d, J = 8.4 Hz, 1H), 7.58 (m, 1H), 1.49 (s, 9H); ESI-MS m/z : 246.10 [M+H]+

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

Reference£º
Patent; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

1569-16-0, 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 is used more and more widely, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

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

Name is 8-Chloro-3-methoxy-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 952059-69-7, its synthesis route is as follows.,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).

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

General procedure: (Method C1) Synthesis of N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine A 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol and 3 equivalents of cesium carbonate (342 mg, 1.048 mmol) in 1.8 mL of DMF. The mixture was stirred at RT for 10 min. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150 C. for 15 min in the microwave, at which time the reaction was determined complete by LC/MS. The mixture was cooled to ambient temperature and diluted with water. The solids were filtered and washed with water. The solids were triturated with methanol, filtered to remove remaining impurities, washed with additional methanol and dried under vacuum to afford N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine as a light orange solid. MS [M+H]=502; Calc’d 501.54 for C30H25N5O3.

952059-69-7 is used more and more widely, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO259,mainly used in chemical industry, its synthesis route is as follows.,215523-34-5

PyBOP (132 mg, 254 muiotaetaomicronIota) was added to a mixture of 1 ,8-naphthyridine-2-carboxylic acid (40.2 mg, 231 muiotaetaomicronIota), 8-amino-2-(2-chloro-4,5-difluorophenyl)-2-azaspiro[4.5]decan-1 -one (isomer 1 , Intermediate I45 ) (80.0 mg, 254 muiotaetaomicronIota) and N,N-diisopropylethylamine (160 muIota, 920 muiotaetaomicronIota) in DMF (2.3 ml) and the mixture was stirred for 2 h at room temperature. For work-up, water (45 ml) and methanol (2 ml) were added and the mixtre was stirred over night. The precipitate was collected by filtration, washed with water and dried to give the title compound 87.0 mg (79 % yield). LC-MS (Method 1 ): Rt= 1.08 min; MS (ESIpos): m/z = 471 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.932 (1.28), 0.949 (1.24), 1.231 (1.28), 1.352 (0.85), 1.591 (0.43), 1.634 (0.73), 1.657 (3.54), 1.665 (3.07), 1.689 (16.00), 1.696 (15.91), 1.732 (4.05), 1.742 (3.41), 1.761 (3.46), 1.772 (3.11), 1.791 (1.62), 1.801 (1.37), 1.855 (5.29), 1.877 (3.07), 1.886 (2.69), 2.069 (0.43), 2.155 (7.04), 2.172 (13.78), 2.190 (7.51), 2.337 (0.81), 2.518 (9.26), 2.523 (6.53), 2.674 (1.79), 2.679 (0.81), 2.888 (0.47), 3.612 (0.51), 3.639 (7.59), 3.656 (13.87), 3.674 (7.34), 3.871 (0.73), 3.897 (1.75), 3.908 (1.66), 3.919 (1.75), 3.946 (0.73), 7.697 (5.21), 7.717 (5.72), 7.724 (5.59), 7.732 (9.13), 7.743 (11.05), 7.753 (8.02), 7.763 (9.30), 7.863 (5.38), 7.884 (5.63), 7.889 (5.80), 7.910 (5.63), 8.264 (15.15), 8.285 (15.66), 8.580 (7.55), 8.586 (7.89), 8.601 (7.64), 8.606 (7.17), 8.680 (15.27), 8.701 (13.82), 8.822 (6.10), 8.844 (5.89), 9.197 (8.96), 9.202 (9.17), 9.208 (8.41), 9.212 (7.94)

With the synthetic route has been constantly updated, we look forward to future research findings about 1,8-Naphthyridine-2-carboxylic acid,belong naphthyridine compound

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 100491-29-0, its synthesis route is as follows.,100491-29-0

EXAMPLE 63 In 10 ml of conc. hydrochloric acid was suspended 500 mg of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and the resulting suspension was subjected to reaction under reflux for 1 hour. The reaction mixture was diluted with 10 ml of water, and the crystals thus deposited were collected by filtration, and then washed with 2 ml of water to obtain 450 mg (yield 97.1%) of 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid having a melting point of 238-242 C. Melting point: 242.5-243.5 C. (recrystallized from chloroform-ethanol (2:1 by volume)).

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Patent; Toyama Chemical Co., Ltd.; US4704459; (1987); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15936-10-4, 2-Chloro-1,8-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,15936-10-4

2-chloro-1,8-naphthyridine (89 mg, 0.54 mmol), 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (100 mg, 0.431 mmol), and cesium carbonate (202 mg, 0.620 mmol) were suspended in dry dimethylformamide (0.86 mL) under nitrogen and heated to 100 C. for 18 h. The mixture was cooled and extracted with ethyl acetate and water. The phases were separated and the organic was dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using the ISCO (0-100% EtOAc in hexane), gave the desired 5-(trans-3-((1,8-naphthyridin-2-yl)amino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (32 mg, 0.089 mmol, 21% yield) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) delta: ppm 1.45 (s, 6H) 2.42 (ddd, J=13.88, 9.28, 3.29 Hz, 2H) 3.44-3.62 (m, 2H) 5.22-5.38 (m, 2H) 6.71 (d, J=8.92 Hz, 1H) 7.16 (dd, J=7.82, 4.46 Hz, 1H) 7.79-7.98 (m, 2H) 8.11 (q, J=3.12 Hz, 2H) 8.84 (dd, J=4.38, 1.90 Hz, 1H).

15936-10-4 2-Chloro-1,8-naphthyridine 5152838, 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;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem