Month: October 2020

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

A. 1.1 g (12.8 mmol) of pivalaldehyde are added to 0.86 g (10 mmol) of 3-amino-pyrrolidine at room temperature and after 1 hour the mixture is diluted with 20 ml of acetonitrile and 10 ml of dimethylformaldehyde. 1.1 g (10 mmol) of 1,4-diazabicyclo-[2.2.2]octane and 3.8 g (10 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate are added and the mixture is stirred overnight at room temperature. The precipitate is filtered off with suction, washed with water and dried in vacuo at 100 C. Yield: 4.25 g (85% of theory) of ethyl 1-(2,4-difluorophenyl)-7-[3-(2,2-dimethyl-propylidene-amino)-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate of melting point: 197-198 C. (with decomposition). 1 H-NMR (CDCl3): delta 1.05 s (9H), 1.4 t (3H), 1.9 m und2.05 m (2H), a broad m at 3.5-3.7 (6H), 4.4 q (2H), 7.05 m (2H), 7.4 m (1H), 8.05 d (1H), 8.35 ppm 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; Bayer Aktiengesellschaft; US5061712; (1991); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-1,5-naphthyridine, and cas is 17965-71-8, its synthesis route is as follows.,17965-71-8

Example 1.1.1 and Example 1.1.2: 3-Bromo-[1 ,5]naphthyridine-5-oxide and 3- bromo-1 ,5-naphthyridine-1 -oxide4.43 g (21.2 mmol, 1 eq) of 3-bromo-1 ,5-naphthyridine (W. Czuba, Recueil des Travaux Chimiques des Pays-Bas 1963, 82, 988-996) were introduced in 165 ml. of methylene chloride. 5.23 g (21.2 mmol, 1 eq) of mefa-chloroperbenzoic acid were then added portionwise at 0 C. The mixture was stirred at rt for 18 h. The mixture was washed with 1 M aqueous NaOH solution and water. Organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 3.08 g of 3-bromo-1 ,5- naphthyridine-5-oxide (pale yellow powder) with 64% yield and 1.00 g of 3-bromo-1 ,5- naphthyridine-1 -oxide (yellow powder) with 21 % yield.3-Bromo-[1 ,5]naphthyridine-5-oxideYield: 3.08 g (64 % of theory). m.p.: 148-149 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9,21 (d, 1 H); 9, 10 (d, 1 H); 8,75 (d, 1 H); 8,06 (d, 1 H); 7,80 (dd, 1 H) ppm. MS: m/z 226 (M+H+).3-Bromo-[1 ,5]naphthyridine-1 -oxide Yield: 1.00 g (21 % of theory), m.p.: 153-154 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9, 12 (d, 1 H); 9,03 (s, 1 H); 8,86 (d, 1 H); 8,36 (s, 1 H); 7,94 (dd, 1 H) ppm.MS: m/z 226 (M+H+).

With the complex challenges of chemical substances, we look forward to future research findings about 17965-71-8,belong naphthyridine compound

Reference£º
Patent; AeTERNA ZENTARIS GMBH; WO2011/64250; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 1,8-Naphthyridine-2-carboxylic acid, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 215523-34-5, its synthesis route is as follows.,215523-34-5

General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM.

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

Reference£º
Article; Talbot, Amelie; Maltais, Rene; Kenmogne, Lucie Carolle; Roy, Jenny; Poirier, Donald; Steroids; vol. 107; (2016); p. 55 – 64;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Example 0757 0757-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (600 mg), 1,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (442 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (174 mg), sodium carbonate (522 mg), 1,4-dioxane (24 mL), and water (2.4 mL) was stirred at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The reaction residue was purified by silica gel column chromatography (chloroform-methanol, NH silica), thereby obtaining 2-chloro-7-(1,3-dimethyl-1H-pyrazol-4-yl)-1,5-naphthyridine (412 mg) as a white solid. MS m/z (M+H): 259.

With the complex challenges 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

952059-69-7, (6- (3-methylisothiazol-5-yl) – [1,2,4] triazolo [4, 3-b] pyridazin-3- yDmethanamine (548 mg, 2225 mumol) and 8-chloro-3-methoxy-l, 5- naphthyridine (576 mg, 2959 mumol) were charged in a microwave vial. 2-butanol (7 mL) was added and the reaction mixture was stirred at 1200C under micro-waves irradiation for 8h. 2M NH3 in MeOH was added. Purification by MPLC (DCM/MeOH+l%NH4OH: 100/0 to 90/10) afforded the title compound (720 mg, 80% yield). MS m/z = 405.1 [M+H]+. Calc’d for C19H16N8OS: 404.46

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

A 0.5 – 2 mL microwave vial was charged with 1- (4- (3- (aminomethyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) -2- fluorophenyl)pyrrolidin-2-one (0.0792 g, 0.243 mmol), 8-chloro- 3-methoxy-l, 5-naphthyridine (0.0590 g, 0.303 mmol), and butan- 2-ol (1.00 ml, 0.243 mmol), sealed, then placed in a Personal Chemistry Microwave for 4 hours at 1200C. The mixture was concentrated, then triturated with MeOH to give 1- (2-fluoro-4- (3- ( (7-methoxy-l, 5-naphthyridin-4-ylamino) methyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) phenyl)pyrrolidin-2-one as the hydrochloric salt .MS (ESI pos. ion) m/z: 485 (MH+). Calc’d exact mass for C25H2IFN8O2: 484.

With the complex challenges of chemical substances, we look forward to future research findings about 952059-69-7,belong naphthyridine compound

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2,5-Dichloro-1,8-naphthyridine, and cas is 91870-15-4, its synthesis route is as follows.,91870-15-4

The product from Example 21d (0.67 g, 3.36 mmol) and the product from Example9c (0.78 g, 3.36 mmol) in 10 mL ethanol were heated under reflux for 5.5 hr. The reaction mixture was cooled to room temperature and the solvent was removed concentrated under vacuum leaving yellow solid that was used without further purification (1.43 g, 100 percent).

91870-15-4 is used more and more widely, we look forward to future research findings about 2,5-Dichloro-1,8-naphthyridine

Reference£º
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
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: C8H14ClNO185,mainly used in chemical industry, its synthesis route is as follows.,952059-69-7

General procedure: (Method C5) Synthesis of N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine A pyrex reaction tube was charged with 8-chloro-3-methoxy-1,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol (80 mg, 0.26 mmol), cesium carbonate (249 mg, 0.76 mmol) and DMSO (2 mL). The tube was sealed and the reaction mixture was heated to 130 C. After 3.5 h, an aliquot was analyzed by LCMS, and the desired product was determined to be the major peak. The reaction mixture was diluted with DMSO and purified by Gilson HPLC {5-65% (0.1% TFA in CH3CN) in H2O over 20 min}. The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with DCM. The organic portion was dried with Na2SO4, filtered, and concentrated to afford material that was further purified by silica gel chromatography, 90/10/1 CH2Cl2/MeOH/NH4OH. This provided N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine as pure material. MS [M+H]=473.01.48 minutes. Calc’d for C28H20N6O2: 472.5.

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; 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

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

EXAMPLE 3 Ethyl 3-(1,5-naphthyridin-2-yl)prop-2-enoate (H1) 2-chloro-1,5-naphthyridine (101 mg, 0.614 mmol), boronate ester B1 (195 mg, 0.920 mmol), S-Phos (25.2 mg, 0.061 mmol), K3PO4 (391 mg, 1.841 mmol) and PdOAc2 (6.89 mg, 0.031 mmol) were combined in a 5-mL microwave vial in THF (2.5 mL) and water (500 mul). The reaction mixture was heated at 100 C for 15 min. The reaction mixture was diluted with EtOAc (20 mL), washed with sat. aq. NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (10 to 100% EtOAc in hexanes) to afford the title compound as a pale orange solid (118 mg, 90%). 1H NMR (500 MHz, DMSO): delta 9.02 (dd, J = 4.1, 1.6 Hz, 1 H), 8.48 (d, J = 8.8 Hz, 1 H), 8.48-8.42 (m, 1 H), 8.25 (d, J = 8.7 Hz, 1 H), 7.84-7.79 (m, 2 H), 7.13 (d, J = 16.0 Hz, 1 H), 4.25 (q, J = 7.1 Hz, 2 H), 1.30 (t, J = 7.1 Hz, 3 H) ppm; LRMS m/z (M+H) 229.2 found, 229.1 required.

With the complex challenges of chemical substances, we look forward to future research findings about 7689-62-5,belong naphthyridine compound

Reference£º
Patent; Merck Sharp & Dohme Corp.; COX, Christopher D.; RAHEEM, Izzat T.; SCHREIER, John D.; (63 pag.)EP2621926; (2017); B1;,
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.

To a solutionof 3-amino-3-pyrrolidin-3-yl-propionitrile (200 mg, 1.44 mmol) and7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydro-[l,8] naphthyridine-3-carboxylic acid(282 mg, 1.00 mmol) in acetonitrile (10mL) was added triethylamine (505 mg, 5.00 mmol) and the solution was heated at 80 C for 17 hours. The precipitate was collected by vacuum filtration and rinsed with acetonitrile. The solid was dried overnight at 45 C under vacuum to give 240 mg of the title compound (yield: 62%). MS (APCI+):mAz 386 (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; WARNER-LAMBERT COMPANY LLC; WO2005/49602; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem