Month: November 2020

It is a common heterocyclic compound, the naphthyridine compound, 2-Chloro-1,5-naphthyridine, cas is 7689-62-5 its synthesis route is as follows.,7689-62-5

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 2- chloro-1 ,5-naphthyridine (2) (329mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15ml_) and H20 (15ml_) were added. The organic phase was separated and the water layer was extracted with EtOAc (15ml_). The organic layers were combined and Pd- scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (121 mg, 27%). (0160) LCMS (ES): Found 224.3 [M+Hf.

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

Reference£º
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-1,7-naphthyridin-8(7H)-one, and cas is 1375301-90-8, its synthesis route is as follows.,1375301-90-8

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 1375301-90-8,belong naphthyridine compound

Reference£º
Patent; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 7-Chloro-1,8-naphthyridin-2-ol, cas is 15944-34-0 its synthesis route is as follows.,15944-34-0

Preparation B 7-methoxy-1H-[1,8]naphthyridin-2-one To a solution of 7-chloro-1H-[1,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 mL) was added NaOMe (25 wt % in MeOH, 161 mL). The resulting solution was stirred at reflux for 15 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*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, 1H); 7.96 (d, J=8.5 Hz, 1H); 7.81 (d, J=9.4 Hz, 1H); 6.63 (d, J=8.5 Hz, 1H); 6.34 (d, J=9.4 Hz, 1H); 3.90 (s, 3H).

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; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,1,6-Naphthyridine-2-carboxylic acid,197507-59-8,Molecular formula: C9H6N2O2,mainly used in chemical industry, its synthesis route is as follows.,197507-59-8

Triethylamine (3.03 ml, 21.8 mmol), ethyl chloroformate (3.73 ml, 39.0 mmol) and 4-dimethylaminopyridine (DMAP) (2.40 g, 19.6 mmol) are added, at O0C, to a solution of l,6-naphthyridine-2-carboxylic acid (138) (Chan, L., Jin, H., Stefanac, T., Lavallee, J.F., Falardeau, G., Wang, W., Bedard, J., May, S. and Yuen, L., J. Med. Chem., 1999, 42, 3023-3025) (1.00 g, 5.75 mmol) in anhydrous dichloromethane (75 ml). After returning to ambient temperature, the reaction mixture is brought to reflux for 5 hours, the solution is evaporated to dryness and then the residue is purified on a column of alumina eluted with ethyl acetate to result in the ester 139 (517 mg, 2.56 mmol). Yield: 45%; Rf: 0.86 (Al2O3, ethyl acetate); melting point: 106-1080C; 1H NMR (400 MHz, CDCl3) d 1.41 (t, 3H, J = 7 Hz), 4.49 (q, 2H, J= 7 Hz), 8.02 (d, IH, J= 6 Hz), 8.21 (d, IH, J= 8.5 Hz), 8.39 (d, IH, J = 8.5 Hz), 8.75 (d, IH, J = 6 Hz), 9.29 (s, IH); 13C NMR (100 MHz, CDCl3) d 14.3, 62.0, 122.4, 122.7, 124.0, 137.2, 147.5, 149.7, 152.3, 152.9, 164.6; IR (KBr) V cm”1 : 1256, 1734; MS (m/z, %) 202 (M+, 3), 158 (18), 130 (100), 102 (15), 75 (22), 51 (16).

With the synthetic route has been constantly updated, we look forward to future research findings about 1,6-Naphthyridine-2-carboxylic acid,belong naphthyridine compound

Reference£º
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); WO2008/12782; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

To a solution of 2-methyl-1,8-naphthyridine (6.024 g, 41.8 mmol) (from step 1) in anhydrous THF (140 mL) at -40 ¡ãC under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (88.0 mL) and the reaction mixture was stirred at -40 ¡ãC for 30 min to give a blood-red solution. After stirring for 30 min at – 40 ¡ãC, neat diethyl carbonate (5.60 mL) was added drop wise to above solution in 5 min and the reaction mixture was warmed up to 0 ¡ãC (ice-bath) and stirred at that temperature for 2 h to give a dark reddish-orange solution. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (60.0 mL) to give an orange-red solution and the THF was removed in vacuo to give an orange-red mixture. The resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4/MgSO4, filtered and evaporated in vacuo to afford a dark orange-red crystalline solid (8.65 g). The crude residue was purified by Silica-gel flash chromatography using a Varian SF-40-120 g Super Flash silica gel column and elution with 10-100percent ethyl acetate in n-heptane to afford the desired product as a yellow-orange crystalline solid (7.76 g, yield 85percent). LC-MS analysis of the solid shows the desired product’s mass: m/z 217 (M+H) and m/z 239 (M+Na); Calculated for C12H12N2O2: 216.23. 1H NMR (400 MHz, DMSO-d6): delta 1.21 (t, J = 7.0 Hz, 3H), 4.10 (q, 2H), 4.89 (s, 1H), 6.77 (d, J = 9.38 Hz, 1H), 7.14 (m, 1H), 7.46 (d, J = 9.36 Hz, 1H), 7.89 (d, 1H), 8.36 (d, 1H), 11.80 (brs, 1H, -OH). 1H NMR of the isolated product was superimposable with that of an authentic sample of the product.

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

Reference£º
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

0390-7 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (29 mg), bis(pinacolato)diboron (36 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (10 mg), potassium acetate (23 mg), and 1,4-dioxane (1 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(3-(4-iodo-3-propyl-1H-pyrazol-1-yl)propyl)morpholine (43 mg), sodium carbonate (25 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (8 mg), and water (0.1 mL) were added thereto, followed by stirring at 80 C. for 3 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-propyl-1H-pyrazol-1-yl)propyl)morpholine (11 mg). MS m/z (M+H): 400., 1309774-03-5

With the rapid development of chemical substances, we look forward to future research findings about 7-Bromo-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 naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

The compound was prepared according to the procedure as described in WO 0033838. To a solution of 2-methyl-1,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35 ml) was added 10percent Pd/C, and the reaction mixture was stirred under H2 (10 psi) for 24 hours. Palladium was filtered out through celite and washed with excess ethanol. The filtrate was concentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) delta 1.82-1.87 (m, 2H), 2.22 (s, 3H), 2.65-2.76 (m, 2H), 3.33-3.36 (m, 2H), 6.32 (d,1H, J=7.25 Hz), 7.07 (d, 1H, J=7.38 Hz). Mass spectrometry: 149.15 (M+H)+.

With the complex challenges of chemical substances, we look forward to future research findings about 1569-16-0,belong naphthyridine compound

Reference£º
Patent; Nagarajan, Srinivasan R.; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; Yi, Yu; Huff, Renee M.; Desai, Bipinchandra N.; Devadas, Balekudru; Parikh, Mihir D.; Penning, Thomas; US2004/92538; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolidine dimethanesulfonate (12. 5g), 2-hydroxybenzaldehyde (8.6g) and triethylamine (12.2g) were in turn introduced into a reaction vessel at room temperature. After stirring the mixture for about 0. 5h, 7- chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8- naphthyridine-3-carboxylic acid (lO. Og) was introduced thereto. The resultant reaction mixture was stirred for about 15h at room temperature, cooled to O~ 5 C, and stirred for about 3h. The title compound in the form of solid was filtered, washed with acetonitrile, and dried to prepare 16.0 g of the title compound (Yield: 91. 8%). ‘H NMR (6, CDC13) : 8. 68 (s, 1H), 8.42 (s, 1H), 8.01 (d, J=12.4Hz, 1H), 7. 30-7. 20 (m, 3H), 6. 90-6. 82 (m, 2H), 4. 68-4. 53 (m, 2H), 4. 32-4. 24 (m, 1H), 4.06 (dd, J1=11. 9Hz, J2=5. 5Hz, 1H), 4. 02-3. 85 (m, 3H), 3.95 (s, 3H), 3.60 (m, 1H), 3.40 (m, 1H), 1. 29-1. 21 (m, 2H), 1. 07-1. 00 (m, 2H) Mass (FAB): 494 (M+H), 100361-18-0

With the rapid development of chemical substances, we look forward to future research findings about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2003/87100; (2003); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

A suspension of (6) (10 g) in 29 mL of 12% HCl and 26 mL of glacial acetic acid was refluxed for 7.5 h. It was cooled, filtered and recrystallized from a boiling mixture of methanol and acetone to yield 6.3 g of (7) m.p.=195-200 C.

With the complex challenges of chemical substances, we look forward to future research findings about 100491-29-0,belong naphthyridine compound

Reference£º
Patent; Vymed Corporation; SHETTY, B. Vithal; US2014/73631; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,7-Naphthyridin-2(1H)-one, and cas is 54920-82-0, its synthesis route is as follows.,54920-82-0

To a solution of lH-l,7-naphthyridin-2-one (1.6 g, 11.0 mmol) in MeOH (50 mL) was added BnBr (2.1 g, 12.1 mmol) at to 70 ¡ãC. The resulting mixture was stirred at 70 ¡ãC for 3 hrs and then cooled to 0 ¡ãC. To the cooled mixture was added NaBH4 (2.09 g, 55.0 mmol). The resulting mixture was slowly warmed to rt and stirred for 3 hrs at rt. The reaction was quenched with 6N HC1 (20 mL). The resulting mixture was stirred at rt for 2 hrs, then basified with 2 N NaOH to pH 10 and extracted with DCM (50 mL) twice. The combined organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by column (eluting with DCM: MeOH =40:1, v:v) to give 7-benzyl-l,5,6,8-tetrahydro-l,7-naphthyridin-2-one (700 mg) as a yellow solid.

With the complex challenges of chemical substances, we look forward to future research findings about 54920-82-0,belong naphthyridine compound

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem