Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

7-F4- (2-HVDROXVETHYLIDENE) PIPERIDIN-1-YLL-1-CVCLOPROPVL-6-FLUORO-4-OXO-1, 4- DIHVDRONAPHTHYRIDINE-3-CARBOXVIIC acid (163) A solution of amine 103 (256 mg, 1.06 MMOL) and triethylamine (0.5 mL, 3.55 MMOL) in ACETONITRILE (4 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4-dihydro-naphthyridine-3- carboxylic acid (200 mg, 0.71 MMOL) under nitrogen and the reaction mixture was allowed to stir for 16 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3 x 10 mL) and allowed to dry overnight to afford the title compound 163 (105 mg, 40%). MS 374 (M+H)., 100361-18-0

100361-18-0 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid 11055142, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); 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.,100361-18-0

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolydine dimethanesulfonate (12. 5g) and 1-naphthaldehyde (11. lg) were in turn introduced into a reaction vessel at room temperature and cooled to 0~5 C. Triethylamine (12.2g) was dropwise added to the reaction mixture. After stirring the mixture for about 0. 5h, the reaction mixture was diluted by adding ethanol (30ml). 7-Chloro-l-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo- 1, 8-naphthyridine-3-carboxylic acid (lO. Og) was introduced to the reaction mixture. After raising slowly the reaction temperature to room temperature, the reaction mixture was stirred for about 15h. The title compound in the form of solid was filtered, washed with water and ethanol, and dried to prepare 15.7 g of the title compound (Yield: 84. 4%). 1H NMR (o, CDCl3) : 8.86 (m, 2H), 8.55 (s, 1H), 7. 82 (m, 3H), 7.73 (m, 1H), 7.40 (m, 3H), 4.60 (m, 2H), 4.24 (m, 2H), 4.08 (m, 1H), 3.99 (m, 1H), 3.95 (s, 3H), 3.45 (m, 2H), 1.13 (m, 2H), 0. 89 (m, 2H) Mass (FAB): 528 (M+H)

With the synthetic route has been constantly updated, 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,belong naphthyridine compound

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 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

l-(2-(7-methoxy-l,5-naphthyridin-4-ylamino)ethyl)-5-(thiophen-2- yl)pyridin-2(lH)-one.; A suspension of 8-chloro-3-methoxy-l,5-naphthyridine (35 mg, 182 mumol) and l-(2-aminoethyl)-5-(thiophen-2-yl)pyridin-2(lH)-one (40 mg, 182 mumol) in iPrOH (0.5mL) was heated to 100C overnight. The mixture was partitioned between CH2Cl2 (10 mL) and IM NaOH (5mL). The aqueous was further extracted with CH2Cl2 (2x 5mL) and combined organics dried over MgSO4 then purified on silica (12 g) eluting with 15-60% of 5% (MeOH/ CH2Cl2). MS (ESI pos. ion) m/z (MH+): 379. Calc’d exact mass for C20H18N4O2S: 378. 1H NMR (400 MHz, Chloroform-d) delta ppm 3.09 (br. s., 1 H) 3.85 (q, J=6.13 Hz, 2 H) 3.93 (s, 3 H) 4.28 (t, J=5.97 Hz, 2 H) 6.57 (d, J=5.48 Hz, 1 H) 6.65 (d, J=9.59 Hz, 1 H) 6.81 (d, J=2.74 Hz, 1 H) 6.91 – 7.00 (m, 2 H) 7.10 – 7.15 (m, 1 H) 7.34 (d, J=2.54 Hz, 1 H) 7.50 – 7.58 (m, 2 H) 8.40 (d, J=2.74 Hz, 1 H) 8.45 (d, J=5.48 Hz, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 3-Bromo-8-chloro-1,7-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1260670-05-0, its synthesis route is as follows.,1260670-05-0

Step 1 To a 100 mL sealed tube was added 3~bromo-8-chloro-l,7-naphthyridine K-l (1.00 g, 4.10 mmol), 1,4-dioxane (15 mL) and NH3_H20 (40 mL) at room temperature. The mixture was sealed and stirred at 100 C for 15 h, then cooled and partitioned between water (150 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (50 mL x 2) and the combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound K-2. MS for K-2: m/e = 224 and 226 (M+l).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); 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 suspension of 6.0 g of 1,7-naphthyridin-2(1H)-one in 60 mL of N,N-dimethylformamide, 2.5 g of 60percent sodium hydride was added at room temperature, and the mixture was stirred at 50 to 60¡ãC for 1 hour. Thereto was added 6.4 mL of 2-bromomethyl-1,3-dioxolan, the temperature was increased to 90 to 95¡ãC, and the reaction mixture was stirred for 2 hours 30 minutes. The temperature was further increased to 95 to 100¡ãC, and the mixture was stirred for 4 hours. Thereto were added 0.82 g of 60percent sodium hydride and 2.1 mL of 2-bromomethyl-1,3-dioxolan and the mixture was further stirred at the same temperature for 2 hours. Thereto were added 0.49 g of 60percent sodium hydride and 1.3 mL of 2-bromomethyl-1,3-dioxolan and the mixture was stirred at 90 to 100¡ãC for 2 hours. Thereto were further added 0.49 g of 60percent sodium hydride and 1.3 mL of 2-bromomethyl-1,3-dioxolan and the mixture was stirred at the same temperature for 4 hours. The reaction mixture was cooled to 5¡ãC, and ethyl acetate and ice water were then added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate = 100:0 to 0:100 and then, using gradient elution with chloroform:methanol = 100:0 to 90:10 to obtain 3.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,7-naphthyridin-2(1H)-one as a brown solid. 1H-NMR (CDCl3) delta: 3.85-3.94 (2H, m), 3.99-4.08 (2H, m), 4.58 (2H, d, J = 4.5 Hz), 5.29 (1H, t, J = 4.5 Hz), 6.91 (1H, d, J = 9.4 Hz), 7.41 (1H, d, J = 5.1 Hz), 7.67 (1H, d, J = 9.4 Hz), 8.45 (1H, d, J = 5.1 Hz), 9.05 (1H, s)

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

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Example 4b: Synthesis of 7-bromo-2-morpholino-l,5-naphthyridine F-32) [00336] A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino- 1,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]+.

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; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) (7.82 g, 0.02 mol) in 10% HCl (100 mL) was refluxed at 100 C for 3h. The reaction mixture was cooled down, diluted with 100 ml of H2O and adjusted to pH=7 by addition of ammonia (33%). The product was filtered off, dried and recrystallized from EtOH., 100491-29-0

With the rapid development 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
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

General procedure: (Method C4) Synthesis of N’-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine In a 20 mL sealed tube was dissolved 8-chloro-3-methoxy-1,5-naphthyridine (70 mg, 360 mumol) in DMF (2.00 mL). To this was added N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine (124 mg, 396 mumol) and the reaction mixture was stirred at 70 C. for 17 h. Upon cooling to RT, the mixture was dissolved in DMF and purified using Gilson reverse phase chromatography. The product fractions were combined, concentrated and the resulting crude was extracted into DCM, washed 1* sodium carbonate, 1*H2O, dried with Na2SO4, filtered through fritted funnel, concentrated to yield N1-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as light yellow solid. MS [M+H]=471.0; Calc’d 470.5 for C29H22N60.

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

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 solution of the compound 0001-2 (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) was stirred at 85C for 5 minutes. A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was dropwise added thereto. Further acetic acid (2 mL) was added dropwise thereto, and the mixture was stirred at 85C for 3 hours. To a 6 M aqueous sodium hydroxide solution (60 mL) under stirring with ice-cooling, the reaction solution which had been cooled to room temperature was added dropwise. The precipitated solid was separated by filtration, and the solid was then suspended in methanol (5 mL), and thereafter subjected to sonication. Thereafter, the suspension was filtered, and then the resulting solid was washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v% aqueous methanol solution (8 mL), subjected to sonication, and then the suspension was filtered, and the residue was then washed with a 75 v/v% aqueous methanol solution twice to obtain a compound 0001-3 (3.33 g) as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.13 (1H, d), 8.77 (1H, dd), 8.53 (1H, dd), 7.91 (1H, d). MS m/z (M+H): 245.

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; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); 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: C8H14ClNO449,mainly used in chemical industry, its synthesis route is as follows.,1309774-03-5

0370-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (300 mg), bis(pinacolato)diboron (469 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (100 mg), potassium acetate (241 mg), and 1,4-dioxane (12.3 mL) was stirred at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate (557 mg), sodium carbonate (261 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (87 mg), and water (1.2 mL) were added thereto, followed by stirring at 110 C. for 1 hour. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane, chloroform-methanol), thereby obtaining tert-butyl 4-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (149 mg) as a white solid. MS m/z (M+H): 414.

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