Tag: M.W:100-200

Name is 5,7-Dichloro-1,6-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 337958-60-8, its synthesis route is as follows.,337958-60-8

To a20 mL vial was added 5,7-dichloro-1,6-naphthyridine, (289.1 mg, 1.45 mmol), tert-butyl (1R,3s,55)-3-amino-8-azabicyclo[3 .2.1 joctane-8-carboxylate (362 mg, 1.60 mmol), DIPEA (0.76 mL, 4.36 mmol), and DMSO (7.26 mL). The vial was capped and the reaction mixture was heated to 110 C and stirred for 16 h. The reaction mixturewas diluted with water and extracted with EtOAc (3 x 20 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford a brown oil, which was purified by column chromatography (24 g column; 0-80% EtOAc in hexanes) to afford the title product as a pale yellow solid (455.2 mg, 69 % yield; 85% purity). (m/z): [M+Hf? calcd for C20H25C1N402 389.17, 391.16 found 391.5.

With the complex challenges of chemical substances, we look forward to future research findings about 5,7-Dichloro-1,6-naphthyridine

Reference£º
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); 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 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

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

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 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

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-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 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

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.

2-Phenyl-[1,8]naphthyridin-3-ol (57 mg), 8-chloro-2-methoxy-[1,5]naphthyridine (50 mg), and 4-dimethylaminopyridine (94 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 130C for 8 hr. The reaction mixture was cooled to room temperature, and an aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (27 mg, yield 28%). 1H-NMR (CDCl3, 400 MHz): delta 3.68 (s, 3H), 7.15 (d, J = 9.0 Hz, 1H), 7.18 (d, J = 5.1 Hz, 1H), 7.40 – 7.42 (m, 3H), 7.46 (dd, J = 4.4, 8.3 Hz, 1H), 7.58 (s, 1H), 8.03 (dd, J = 2.0, 8.3 Hz, 1H), 8.32 (d, J = 9.3 Hz, 1H), 8.38 – 8.41 (m, 2H), 8.69 (d, J = 5.1 Hz, 1H), 9.10 (dd, J = 2.0, 4.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 403 (M+Na)+, 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; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); 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

A stirred solution of 2-methyl-l,8-naphthyridine (57.5 g, 399 mmol) (available from Manchester Organics) and ( ?)-fe/ -butyl 3-(iodomethyl)pyrrolidine-l-carboxylate (124.2 g, 399 mmol) (Intermediate 1) in THF (1 L) was cooled to 0 ¡ãC and treated under nitrogen with a solution of lithium bis(trimethylsilyl)amide in THF (1M, 399 ml_, 399 mmol) over 20 min and the reaction mixture was stirred at 0 ¡ãC for 3 h. The reaction was quenched with saturated ammonium chloride solution (500 ml.) and water (500 ml.) and ethyl acetate (1 L) was added. The layers were separated and the aqueous phase was extracted with further ethyl acetate (1 L). The combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The residual brown oil (162 g) was purified by chromatography on a silica cartridge (750 g) eluting with a gradient of 0 – 100 percent [ethyl acetate in (5percent MeOH – 95 percent ethyl acetate)] over 8 column volumes. The appropriate fractions were combined and evaporated in vacuo to give the title compound (46.65 g, 36percent) as an orange solid: LCMS (System A) RT = 0.99 min, 97percent, ES+ve m/z 32S (M+H)+, [a]D20 = + 22 (c 1.00 in EtOH).

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; FALLON, Brendan John; PRITCHARD, John Martin; WO2014/154725; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem