Tag: M.W:100-200

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

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

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 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

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.

: A mixture of 2-methyl-1,8-naphthyridine (250 mg, 1.734 mmol), 1H-indazole-5-carbaldehyde (253 mg, 1.734 mmol) and 4-methylbenzenesulfonamide (297 mg, 1.734 mmol) in toluene (4 mL) was heated at 110 ¡ãC overnight. The reaction was cooled to rt and diluted with EtOAc (15 mL). The solid was collected via filtering and rinsed with EtOAc (2 x 2 mL) and dried in vacuum to afford Intermediate E2A (415 mg, 1.524 mmol, 88percent yield). The crude product was used in the next reaction without further purification. LCMS (ES): m/z 273.2 [M+H]+., 1569-16-0

With the rapid development of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; MORALES, Christian L.; HIGGINS, Mendi A.; MULL, Eric; (318 pag.)WO2018/89357; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2-Chloro-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 7689-62-5, its synthesis route is as follows.,7689-62-5

(3) N-(2-chloro-5-(l,5-naphthyridin-2-yl)-3-pyridinyl)-4- fluorobenzenesulfonamide.; To a 50 mL round-bottomed flask was added 2-chloro-l,5- naphthyridine (54 mg, 328 mumol), N-(2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (135 mg, 328 mumol), tetrakis(triphenylphosphine)palladium (38 mg, 33 mumol), sodium carbonate (70 mg, 656 mumol), dioxane (3 mL). The reaction mixture was stirred at 100 0C for 30 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (3 mL) and extracted with EtOAc (2 X 30 mL). The organic extract was washed with saturated NaCl (2 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 80% EtOAc/hexanes to give N-(2-chloro-5-(l,5-naphthyridin-2- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (78 mg, 57% yield) as a white solid. MS (ESI pos. ion) m/z calc’d for Cl9H12ClFN4O2S: 414.0; found 415.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 7.07 (s, 1 H) 7.16 (t, J=8.55 Hz, 2 H) 7.73 (dd, J=8.55, 4.17 Hz, 1 H) 7.88 (dd, J=8.92, 4.97 Hz, 2 H) 8.11 (d, J=8.77 Hz, 1 H) 8.49 (d, J=8.48 Hz, 1 H) 8.55 (d, J=8.77 Hz, 1 H) 8.83 (d, ./=2.19 Hz, 1 H) 8.94 (d, ./==2.19 Hz, 1 H) 9.03 (dd, J=4.09, 1.61 Hz, 1 H)

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

Reference£º
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 1,8-Naphthyridin-2-amine, cas is 15992-83-3 its synthesis route is as follows.,15992-83-3

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.

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

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO113,mainly used in chemical industry, its synthesis route is as follows.,254-79-5

[000712j To a solution of Compound 90A (1.0 g, 7.69 mol) in acetic acid (8 mL) was added NaOAc (1 .26 g, 15.38 mmol) and a solution of bromine (0.43 mL, 8.46 mmol) in acetic acid (2 mL) at 85 C. The mixture was stirred at 85 C for four hours, cooled to room temperature, and filtered. The filtrate was concentrated under vacuum and the residue was purified with flash column chromatography on silica gel (petroleum in ethyl acetate, 30% v/v) to render Compound 90B. LC-MS (ESI) mlz: 209 [M+H] ?H-NMR (CDC13, 400 MHz) 5 (ppm) 7.70 (dd, J= 4.0, 8.8 Hz, 1H), 8.43 (d, J= 8.4 Hz, 1H), 8.63 (d, J 2.4 Hz, 1H), 7.45 (t,J=2.4Hz, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about 1,5-Naphthyridine,belong naphthyridine compound

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; WO2015/65937; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

The 2-[2-methoxy-4-(6-methoxy-l55~naphthyridm-4-yloxy)phenyl]acetic acid used as a5 starting material was prepared as follows :; -Under an atmosphere of argon, a mixture of 4-chloro-6-methoxy-l,5-naphthyridine (0.97 g), tert-bvLtyl 2-(4-hydroxy-2-methoxyphenyl)acetate (1.19 g), caesium carbonate (3.26 g) and DMF (10 ml) was stirred and heated to 13O0C for 3.5 hours. The resultant mixture was cooled to ambient temperature and partitioned between ethyl acetate and water.I0 The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether and ethyl acetate as eluent. There was thus obtained tert-bxxtyl 2-[2-methoxy- 4-(6-methoxy-l,5-naphthyridin-4-yloxy)phenyl]acetate (1.22 g); 1H NMR Spectrum: (DMSOd6) 1.41 (s, 9H)5 3.51 (s, 2H), 3.75 (s, 3H)5 3.94 (s, 3H)5 6.71 (m5 IH), 6.92 (m, 2H)5 is 7.24 (d5 IH)5 7.29 (d, IH)5 8.27 (d5 IH)5 8.61 (d, IH)., 249889-68-7

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-2-methoxy-1,5-naphthyridine

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,1,6-Naphthyridine,253-72-5,Molecular formula: C8H6N2,mainly used in chemical industry, its synthesis route is as follows.,253-72-5

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).

With the synthetic route has been constantly updated, we look forward to future research findings about 1,6-Naphthyridine,belong naphthyridine compound

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