Month: November 2020

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

Intermediate 139: fert-Butyl ll-[2-f7-chloro-2-oxo-1.8-naphthyridin-l(2H)- yl)ethyl]piperidin-4-yl)carbamateA solution of 7-chloro-l,8-narhohthyridin-2(lH)-one FJ. Ore. Chem. 1990, 55, 4744- 4750] in dry DMF (20 mL) (540 mg, 3.0 mmol) at O0C was treated with sodium hydride (144 mg, 60% in mineral oil, 3.6 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction was cooled using an ice bath. A solution of 2- {4-[(fert-butoxycarbonyl)amino]piperidin-lyl} ethyl methanesulfonate in DMF (Intermediate 6), 0.33 mmol/ mL, 10 mL, 3.3 mmol) was then added over 1 hour. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with water and extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed with saturated sodium chloride solution (3 x 10 mL), dried over sodium sulfate and evaporated. Chromatography on silica gel using methanol in dichloromethane (0-15%) gave the title compound as a brown foam (711 mg, 58%).MS TES): 407 (MH)+ for C20H27ClN4O3 1H NMR rCDChU 1.42 (s, HH); 1.84 – 1.99 (m, 2H); 2.12 – 2.22 (m, IH); 2.22 -2.37 (m, 2H); 2.66 – 2.80 (m, 2H); 3.03 – 3.19 (m, IH); 3.39 – 3.55 (m, IH); 4.34 – 4.48 (m, IH); 4.62 (t, 2H); 6.72 (d, IH); 7.15 (d, IH); 7.61 (d, IH); 7.78 (d, IH).

With the complex challenges of chemical substances, we look forward to future research findings about 15944-34-0,belong naphthyridine compound

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/134378; (2006); 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: C8H14ClNO6,mainly used in chemical industry, its synthesis route is as follows.,1309774-03-5

0157-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 5-methoxypyridine-3-amine (25 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg), and cesium carbonate (33 mg) in 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 6-chloro-N-(5-methoxypyridin-3-yl)-1,5-naphthyridine-3-amine (5.4 mg). MS m/z (M+H): 287.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine,belong naphthyridine compound

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 1,8-Diazanaphthalene, and cas is 254-60-4, its synthesis route is as follows.,254-60-4

Example 125: 4-Chloro-N-[5-chloro-2-(3,4-dihvdro-2H-H ,81naphthyridine-1 – carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide; [00531] 5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (208 mg, 0.50 mmol), 1 ,2,3,4-tetrahydro-[1 ,8]naphthyridine [(135 mg, 1.0 mmol) 1 ,2,3,4-tetrahydro-[1,8]naphthyridine was prepared freshly from 1,8- napthyridine via hydrogenation over Pt2O], BOP (486 mg, 1.1 mmol), DIEA (185 mg, 1.4 mmol) were reacted according to the procedure for the synthesis of 5- chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)-picolinic amides. HPLC purification (20 ? 90% gradient of MeCN-water) provided 4-chloro-N-[5-chloro- 2-(3,4-dihydro-2H-[1 ,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl- benzenesulfonamide: MS m/z. 531.0 (M+H).

With the complex challenges of chemical substances, we look forward to future research findings about 254-60-4,belong naphthyridine compound

Reference£º
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); 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

0398-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), bis(pinacolato)diboron (62 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (16 mg), potassium acetate (40 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 3-(4-Iodo-1H-pyrazol-1-yl)pyridine (61 mg), sodium carbonate (43 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (17 mg), and water (0.2 mL) were added thereto, followed by stirring at 80 C. for 8 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-hexane), thereby obtaining 2-chloro-7-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine (27 mg). MS m/z (M+H): 308.

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

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 belong naphthyridine compound,4-Chloro-1,8-naphthyridine,35170-94-6,Molecular formula: C8H5ClN2,mainly used in chemical industry, its synthesis route is as follows.,35170-94-6

To a solution of 0.5 g (3.04 mmol) of 4-chloro-[1,8]naphthyridine in 10 mL of DMF was added 0.39 g (6.08 mmol) of NaN3. The mixture was stirred for 5 h at 60C. The reaction was allowed to cool to roomtemperature and diluted with 300 ml. of EtOAc, washed with water, brine and dried over Na2SO4. The desiccant was filtered off and the solvents were evaporated under vacuum to give 0.5 g of 4-azido-1,8- naphthyridine as a light brown solid.To a solution of 0.5 g (2.92 mmol) of 4-azido-1,8-naphthyridine in 30 mL of THF was added 100mg of 10% Pd/C. The mixture was hydrogenated at 30C under atmospheric pressure for 5 h. The catalyst wasremoved by filtration. The solvent was evaporated to give 420 mg of 1 ,8-naphthyridin-4-amine a crude product as a light brown solid.To a solution of 0.42 g (2.89 mmol) of 1,8-naphthyridin-4-amine in 50 mL of DCM were added 0.64 g (2.89 mmol) of Boc2O, 0.11 g (0.87 mmol) of DMAP and 1.43 mL (8.68 mmol) of DIPEA and then the mixture was stirred at 30C for 16 h. The solvent was removed under vacuum and the residue waspurified by column chromatography eluting with DCM/MeOH (20/1, R1= 0.4) to give 350mg of tertbutyl N-(1 ,8-naphthyridin-4-yl)carbamate as a brown solid.A suspension of 280mg (1.14 mmol) of tert-butylN-(1,8-naphthyridin-4-yl)carbamate and 164 mg (0.12 mmol) of NaH in 2 ml. of THF was stirred at 40C for 16 h. A solution of 0.04 g (0.13 mmol) of 4- bromo-6-(bromomethyl)isoquinoline in 2 mL of THF was added thereto at 3 5C. The mixture was stirredat 35C for additional 0.5 h. The reaction was quenched with saturated aqueous NH4C1 solution. The mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the product as a light brown semisolid which was purified by preparative HPLC to give 140 mg of tert-butyl N-[l- [(4-bromo-6-isoquinolyl)methyl] -1, 8-naphthyridin- 1 -ium-4- yl]carbamate as a light brown solid.MS (+ESI): 465.0, 467.0 [M+H].?H NMR (400 MHz, DMSO-d6+ D20) ppm: 9.23 (s, 1H), 9.04 (m, 2H), 8.68 (s, 1H), 8.25 (d, J 8.0 Hz, 1H), 8.13 (d, J= 8.8 Hz, 1H), 7.94 (s, 1H), 7.66 (m, 2H), 7.55 (d, J= 4.8 Hz, 1H), 5.25 (br s, 2H), 1.27 (s, 9H).

With the synthetic route has been constantly updated, we look forward to future research findings about 4-Chloro-1,8-naphthyridine,belong naphthyridine compound

Reference£º
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
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 (3.0 g, 20.7 mmol) in CH2CI2 (300 ml) was added Lambda/-chlorosuccimide (11.1 g, 81.6 mmol) and AIBN (15 mg). The reaction was refluxed for 4h with additional AlBN (7mg) added each hour, followed by reflux for 3Oh. The cooled reaction solution was washed well with aqueous Na2COs, brine, dried over MgSO4, and concentrated to give the desired product (5.12g, 100percent) as a tan solid:LC/MS (ES) m/z 247.2 [M+H]+

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/16610; (2007); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

-CHLORO-1-CYCLOPROPYL- 6-fluoro-4-oxo-1, 4-dihydronaphthyridine-3-carboxylic acid (57 mg, 0.2016 MMOL), amine 128 (R5 = F) (67 mg, 0. 2389 MMOL) and triethylamine (0.5 mL) in ACETONITRILE (10 mL) were heated at reflux temperature overnight. After cooling,

With the complex challenges of chemical substances, we look forward to future research findings about 100361-18-0,belong naphthyridine compound

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); A1;,
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

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine 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 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; Pharmacia Corporation; US6921767; (2005); B2;,
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 mixture of 2-methyl-l,8-naphthyridine (115 mg, 0.799 mmol), E6A (148 mg, 0.799 mmol), and 4-methylbenzenesulfonamide (137 mg, 0.799 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu Omicron18 30 chi 100 mm; 10 min gradient from 85percent A: 15percent B to 0percent A: 100percent B (A = 90percent H2O/10 percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E6B (170 mg, 68percent yield). LCMS (ES): m/z 312.2 [M+H]+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

A glass microwave reaction vessel was charged with 1-(trans-4-aminocyclohexyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.1050 g, 0.339 mmol), 2-chloro-1,5-naphthyridine (0.067 g, 0.407 mmol, 00358), and diisopropylethylamine (0.177 ml, 1.017 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (0.484 ml) and heated to 120 C. for 2 days. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, 100*50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 15 min. Fractions containing product were collected and concentrated. The product was taken up in DCM and loaded onto a Silicycle Si-carbonate cartridge and washed with DCM and MeOH to remove any salts to give the title compound (6.4 mg, 0.016 mmol, 4.7% yield). LCMS showed product peak at 1.434 min (m+1=402.0). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.09-1.24 (m, 4H) 1.37-1.53 (m, 2H) 1.94 (d, J=11.93 Hz, 2H) 2.39 (d, J=12.13 Hz, 2H) 2.68 (qd, J=12.91, 3.13 Hz, 2H) 2.97-3.09 (m, 1H) 4.08-4.24 (m, 1H) 4.47 (tt, J=12.32, 3.91 Hz, 1H) 6.85 (d, J=9.19 Hz, 1H) 7.45 (dd, J=8.41, 4.30 Hz, 1H) 7.91-7.96 (m, 2H) 7.97 (d, J=8.61 Hz, 1H) 8.03 (d, J=9.19 Hz, 1H) 8.60 (d, J=3.33 Hz, 1H)

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; 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