Heterocyclic Building Blocks-Naphthyridine

The naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine,cas is 952059-69-7, mainly used in chemical industry, its synthesis route is as follows.

952059-69-7, Step 1: 8-Chloro-1,5-naphthyridin-3-ol A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (1200 mg, 6166 mumol), boron tribromide (6412 mul, 67825 mumol) and dichloroethane (10277 mul, 6166 mumol). The vessel was sealed and the mixture was stirred at 60 C. for 16 h. The reaction mixture was carefully diluted with DCM, and the solids were filtered. The crude material was purified by silica gel chromatography with 40-70% (90:10:1 DCM/MeOH/NH4OH)/DCM to afford 8-chloro-1,5-naphthyridin-3-ol. MS:[M+H]=181.

As the rapid development of chemical substances, we look forward to future research findings about 952059-69-7

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

A common heterocyclic compound, the naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine,cas is 952059-69-7, mainly used in chemical industry, its synthesis route is as follows.

952059-69-7, 2-(2-((7-Methoxy-l,5-naphthyridin-4-yl)(methyl)amino)ethyl)-6-(4- methylthiophen-2-yl)pyridazin-3(2H)-one. A suspension of 2-(2- (methylamino)ethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (275 mg, 1103 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (193 mg, 993 mumol) in iPrOH (5 mL) was heated to 100 C for 18 h in an appropriately sealed vial. The mixture was partitioned between CH2Cl2 (30 mL) and IM NaOH (10 mL), and the organic dried over MgSO4. After concentration under reduced pressure, the organic residue was dissolved in iPrOH (2 mL) and the rsulting crystalized solid was washed with iPrOH (2x 0.5 mL) then dried under reduced pressure. MS (ESI pos. ion) m/z (MH+): 408. Calc’d exact mass for C2ieta2iN5O2S: 407. 1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H) 3.22 (s, 3 H) 3.83 (s, 3 H) 4.51 (t, J=5.77 Hz, 2 H) 4.75 (t, J=5.77 Hz, 2 H) 6.55 (d, J=5.52 Hz, 1 H) 6.60 (d, J=9.54 Hz, 1 H) 6.91 (s, 1 H) 6.97 (s, 1 H) 7.19 (d, J=9.54 Hz, 1 H) 7.32 (d, J=3.01 Hz, 1 H) 8.32 (d, J=5.52 Hz, 1 H) 8.46 (d, J=2.51 Hz, 1 H).

As the rapid development of chemical substances, we look forward to future research findings about 952059-69-7

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); 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.7689-62-5,2-Chloro-1,5-naphthyridine,as a common compound, the synthetic 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.

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

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

A common heterocyclic compound, the naphthyridine compound, name is 3-Bromo-1,5-naphthyridine,cas is 17965-71-8, mainly used in chemical industry, its synthesis route is as follows.

To a stirred solution of 3-bromo-l,5-naphthyridine (C-2) (35.6 g, 170 mmol, 1.0 eq) in dichloromethane (300 mL) at 0C was added w-chloroperbenzoic acid (35.27 g, 204 mmol, 1.2 eq) in portions. The resulting mixture was stirred for lh at RT. The reaction was complete based on TLC analysis. The reaction mixture was washed with saturated Na2S03 solution and saturated NaHC03 solution sequentially, and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (1-5% MeOH-DCM) to afford the desired product 3-bromo-l,5-naphthyridine-5-oxide (C-3) (28.35 g, 74% yield). ‘H NMR (300 MHz, CDCl3-17965-71-8, As the rapid development of chemical substances, we look forward to future research findings about 17965-71-8

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

A common heterocyclic compound, the naphthyridine compound, name is 1,5-Naphthyridin-2(1H)-one,cas is 10261-82-2, mainly used in chemical industry, its synthesis route is as follows.

To a suspension of Intermediate 3 (5.9 g) in dry DME (180 ml) and dry DMF (45 ml) at 0C under argon was added in portions NaH (60% w:w dispersion in mineral oil, 3.2 g). After stirring for 45 minutes, the mixture was treated with lithium bromide (8.8 g) and the suspension was allowed to warm to room temperature. After stirring for 45 minutes, the mixture was treated with allyl bromide (7 ml) and then stirred at 65C for 3 h. The mixture was cooled to room temperature and concentrated under reduced pressure, then t-BuOMe (300 ml) was added and the mixture was then washed with 1 N NH4Cl (200 ml). The combined aqueous phases were extracted with t-BuOMe (2 x 100 ml). The organic phases were combined, washed with brine (200 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (4.29 g, 57%). To obtain an additional amount of the desired compound, the combined aqueous phases were extracted exhaustively with CH2Cl2. Then, the organic extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (1.5 g, 20%). [ES MS] m/z 187 (MH+).

10261-82-2, As the rapid development of chemical substances, we look forward to future research findings about 10261-82-2

Reference£º
Patent; GLAXO GROUP LIMITED; EP2080761; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The naphthyridine compound, name is 7-Chloro-1,8-naphthyridin-2-ol,cas is 15944-34-0, mainly used in chemical industry, its synthesis route is as follows.

10. i. 7-methoxy-lH-[l, 8]naphthyridin-2-one:To a solution of 7-chloro-lH-[l,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 niL) was added sodium methoxide (25 wt% in MeOH, 161 mL). The resulting solution was stirred at reflux for15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added.The phases were separated and the aq layer was extracted with EA (8 x 80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid(5.22 g, 100% yield).1H NMR (d6DMSO) delta: 11.96 (s, 1eta); 7.96 (d, J = 8.5 Hz, IH); 7.81 (d, J = 9.4 Hz, IH); 6.63 (d, J = 8.5 Hz, IH); 6.34 (d, J = 9.4 Hz, IH); 3.90 (s, 3H).

15944-34-0, As the rapid development of chemical substances, we look forward to future research findings about 15944-34-0

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/147616; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem