Heterocyclic Building Blocks-Naphthyridine

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 3 Ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol -1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate A mixture of ethyl 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (91 mg, 0.5 mmol), 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (259 mg, 1.5 mmol), and DBU (380 mg, 2.5 mmol) in CH3 CN (20 ml) was heated under reflux for 2 h, cooled to r.t. and stirred further for 18 h, diluted with water. Unreacted starting materials were removed by extraction with chloroform. The water layer was concentrated to give a yellow oil. Yield: 150 mg, 62%. 1 H NMR (CDCl3) delta: 1.3 (t, 3H), 2.5 (m, 2H), 3.9 (m, 4H), 4.4 (q, 2H), 5.3 (m, 1H), 7.3 (m, 4H), 7.8 (d, 1H), 8.0 (d, 1H), 8.4 (s, 1H).

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; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 2-Chloro-1,7-naphthyridine, cas is 35192-05-3 its synthesis route is as follows.,35192-05-3

Step B: Preparation of 4, [4-DIMETHYL-7- [2- ( [1,] 7] [NAPHTHYRIDIN-2-YLAMINO)-BENZOYLAMINO]-3, 4-DIHYDRO-LH-] isoquinoline-2-carboxylic acid tert-butyl ester A mixture of [7- (2-AMINO-BENZOYLAMINO)-4,] 4-dimethyl- 3, [4-DIHYDRO-LH-ISOQUINOLINE-2-CARBOXYLIC] acid tert-butyl ester (Step A, 303 mg, 0.77 mmol), 2-chloro- [1, 7] [NAPHTHYRIDINE (126] mg, 0. [77 MMOL), PD2 (DBA)] 3 (7.1 mg, 0.008 [MMOL),] 2-dicyclohexyl [PHOSPHINO-2′- (N-N-] dimethyamino) biphenyl (8 mg, 0.02 [MMOL),] and LiN (TMS) 2 (1 M solution in THF, 2.3 mL) was heated at [80 C] for 12 h. The mixture was concentrated in vacuo and the crude material was purified with flash chromatography [(SI02,] 5% [MEOH/CH2CL2)] to obtain the titled compound. MS [(ES+)] : 524.0 [(M+H) +. CALC’D] for [C31H33NSO3-523.] 63.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Chloro-1,7-naphthyridine

Reference£º
Patent; AMGEN INC.; WO2004/5279; (2004); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Bromo-2-chloro-1,5-naphthyridine, and cas is 1309774-03-5, its synthesis route is as follows.,1309774-03-5

A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino-l,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]

With the complex challenges of chemical substances, we look forward to future research findings about 1309774-03-5,belong naphthyridine compound

Reference£º
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
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: C8H14ClNO208,mainly used in chemical industry, its synthesis route is as follows.,952059-69-7

Example 40 (Method C4)Synthesis of N1-(7-methoxy-l,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-l- yl)benzene-l,4-diamine; In a 20 mL sealed tube was dissolved 8-chloro-3-methoxy-l,5-naphthyridine (70 mg, 360 mumol) in DMF (2.00 mL). To this was added Nl-(4-phenylphthalazin-l-yl)benzene-l,4- diamine (124 mg, 396 mumol) and the reaction mixture was stirred at 70 0C for 17 h. Upon cooling to RT, the mixture was dissolved in DMF and purified using Gilson reverse phase chromatography. The product fractions were combined, concentrated and the resulting crude was extracted into DCM, washed 1 x sodium .carbonate, 1 x H2O, dried withNa2SO4, filtered through fritted funnel, concentrated to yield Nl-(7-methoxy-l,5- naphthyridin-4-yl)-N4-(4-phenylphthalazin-l-yl)benzene-l,4-diamine as light yellow solid. MS [M+H]=471.0; Calc’d 470.5 for C29H22N6O.

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

Reference£º
Patent; AMGEN INC.; WO2008/124083; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

0001-3 A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was added dropwise to a mixture of 2-chloro-1,5-naphthyridine (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) at 85 C., and acetic acid (2 mL) was added thereto, followed by stirring at 85 C. for 3 hours. The reaction mixture was cooled to room temperature, and added dropwise to a 6 mol/L sodium hydroxide aqueous solution (60 mL) under ice-cooling. The solid matter was collected by filtration, suspended in methanol (5 mL), and subjected to an ultrasonic treatment. The solid matter was collected by filtration, and washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v % methanol aqueous solution (8 mL), the resultant product was subjected to an ultrasonic treatment, and the solid matter was collected by filtration, thereby obtaining 7-bromo-2-chloro-1,5-naphthyridine (3.33 g) as a pale yellow solid. MS m/z (M+H): 243.

7689-62-5 is used more and more widely, we look forward to future research findings about 2-Chloro-1,5-naphthyridine

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;,
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: C8H14ClNO251,mainly used in chemical industry, its synthesis route is as follows.,55716-28-4

B. 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0 C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3*500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101 C.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Methoxy-1,7-naphthyridin-6-amine,belong naphthyridine compound

Reference£º
Patent; Novartis AG; US6136821; (2000); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one To a solution of 6-bromo-1,8-naphthyridin-2(1H)-one (0.1 g, 0.444 mmol) in DMF (2 mL) was added sodium hydride (0.021 g, 0.889 mmol) at 0 C. The reaction was stirred at 0 C. for 30 min, then SEM-Cl (0.118 mL, 0.667 mmol) was added. The reaction was stirred at room temperature overnight, then diluted with ammonium chloride solution, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether to give 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one (0.12 g, 76%). 1HNMR 400 MHz (CDCl3): 0.034 (s, 9H), 0.95-0.99 (m, 2H), 3.73-3.77 (m, 2H), 5.92 (s, 2H), 6.75-6.77 (m, 1H), 7.56-7.58 (m, 1H), 7.96-7.98 (m, 1H), 8.63-8.64 (m, 1H).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); 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

10g and 11.1gThe 1,5-naphthyridine derivative is dissolved in DMF.2.51 g of sodium hydride was added in portions on an ice bath.Add 5 minutes at room temperature after adding,After stirring for 2 hours at 50C,TLC showed that the raw material spots almost disappeared.Cool the reaction solution to ice bathIn an ice bath,Add 2.51g of sodium hydride,After stirring for 5 minutes,Add 4.5 ml acetyl chloride,There are a lot of white solids in the solution,After stirring for 3h at room temperature,Add 200ml of water to quench unreacted sodium hydride,Add 400ml of ethyl acetate to extractThe organic layer is washed three times,100ml each time.The organic layer is dry,concentrate,The concentrated oil was dissolved in 200 ml of THF.Join 37g TBAF,Stir at room temperature,The reaction gradually turned black.Stop the reaction after 30 minutes,Diluted the reaction with 100 ml of ethyl acetateWash 3 times,30ml each time.After the ethyl acetate layer is dry,concentrate,Get crude product.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 7-Chloro-1,8-naphthyridin-2-ol, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 15944-34-0, its synthesis route is as follows.,15944-34-0

To a solution of 3.2 g of 7-chloro-1,8-naphthyridin-2(1H)-one in 32 mL of N,N-dimethylformamide, 3.7 g of potassium carbonate was added, and the mixture was stirred at 50 to 60C for 23 minutes, and then, thereto was added 2.2 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 60 to 78C for 25 minutes. Thereto were added 16 mL of N,N-dimethylformamide and 1.1 mL of 2-bromomethyl-1,3-dioxolan, the mixture was stirred at 90 to 95C for 2 hours 15 minutes, 3.7 g of potassium carbonate was added thereto, and the mixture was stirred for 20 minutes. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate = 1:1 to obtain 3.6 g of 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one as a yellow solid. 1H-NMR (CDCl3) delta: 3.86-3.96 (2H, m), 4.10-4.20 (2H, m), 4.63 (2H, t, J = 5.4 Hz), 5.60 (1H, t, J = 5.4 Hz), 6.75 (1H, d, J = 9.6 Hz), 7.17 (1H, d, J = 8.0 Hz), 7.62 (1H, d, J = 9.6 Hz), 7.79 (1H, d, J = 8.0 Hz)

With the complex challenges of chemical substances, we look forward to future research findings about 7-Chloro-1,8-naphthyridin-2-ol

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); 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 flask was charged with SeO2 (1.3 g, 11.7 mmol), 1,4-dioxane (20 mL) and a few drops of water. After the solution was refluxed for a few minutes, 2-methyl-1,8-naphthyridine (1 g, 6.9 mmol) was slowly added and the mixture turned red. The solution was then maintained at then continuing refluxed for another 3 h and during this time the red solution changed to brownish black. The hot solution was then filtered and the solvent was removed in vacuum. The resulting residue was dissolved in CH2Cl2, washed with water (3 x 30 mL), dried over Na2SO4 and concentrated under vacuum to give a brown solid. m.p. 65-68 ¡ãC. Yield: 60percent (0.67 g, 4.2 mmol). 1H-NMR (400 MHz, CDCl3) delta (ppm): 10.32 (s, 1H), 9.28-9.27 (m, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.32 (dd, J = 8.4 Hz, J = 1.2 Hz, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.63 (dd, J = 8.4 Hz, J = 4 Hz, 1H). 13C-NMR (100 MHz, CDCl3) delta: 193.5, 155.6, 155.4, 154.9, 138.8, 137.1, 125.2, 124.0, 118.3 ppm. Anal. Calcd for C9H6N2O: C 68.35; H 3.82, N 17.71. Found: C 68.21; H 3.56, N 17.85.

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

Reference£º
Article; Liu, Guiyan; Liu, Chengxin; Han, Fangwai; Wang, Zhongliang; Wang, Jianhui; Tetrahedron Letters; vol. 58; 8; (2017); p. 726 – 731;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem