Heterocyclic Building Blocks-Naphthyridine

Name is 1,6-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 253-72-5, its synthesis route is as follows.,253-72-5

To a stirred solution of [1,6]-naphthyridine (4.73 g, 36.4 mmol) in CCl4 (200 mL) was added Br2 (2.25 mL, 43.7 mmol) in CCl4 (35 mL) dropwise via an addition funnel. The resulting solution was heated at reflux for 1 hour. Pyridine (2.94 mL, 36.4 mmol) in CCl4 (30 mL) was added dropwise to the refluxing solution, and the mixture was refluxed overnight. The cooled reaction mixture was filtered, and the solids were digested with 1 M NaOH (200 mL) for 1 hour. The basic solution was extracted into CH2Cl2 (2 x 200 mL), and the organic fractions were combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (10percent EtOAc/CH2Cl2) affording 2.03 g (27percent) of the title compound as yellow crystals: mp 79-81 ¡ã

With the complex challenges of chemical substances, we look forward to future research findings about 1,6-Naphthyridine

Reference£º
Patent; Wyeth; EP1147083; (2004); B1;,
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

a) 1,2,3,4-Tetrahydro-1,8-naphthyridine 1,8-Naphthyridine (1.0 g, 7.68 mmole) was hydrogenated (50 psi) with 10% Pd/C (100 mg) in absolute ethanol (40 mL) for 18 hr. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give the title compound (1.04 g) which was sufficiently pure for use in the next step: MS (ES) m/e 135 (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; Affinium Pharmaceuticals, Inc.; EP1226138; (2004); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH.

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
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

Name is 1,8-Naphthyridin-2-amine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 15992-83-3, its synthesis route is as follows.,15992-83-3

Preparation of 2-(1,8-naphthyridin-2-yl)phthalimide (8.6 g.), m.p. 250 C., by reacting 2-amino-1,8-naphthyridine (9.9 g.) with phthalic anhydride (10.2 g.) in dimethylformamide (75 cc.) at 150 C. for 1 hour 30 minutes.

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

Reference£º
Patent; Rhone-Poulenc S.A.; US4016274; (1977); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Step 1 To a mixture of 3-bromo-8-chloro-l ,7-naphthyridine J-1 (4.00 g, 16.4 mmol), but-2-yn-l-ol (1.78 g, 24.6 mmol), Cs2C03 (8.03 g, 24.6 mmol), and 5-(di-ieri-butylphosphino)-l’,3′,5′- triphenyl-rH-l ,4′-bipyrazole (1.67 g, 3.29 mmol) in THF (40 mL) was added diacetoxypalladium (0.574 g, 1.64 mmol) under N2. The mixture was stirred at 70 C for 4 h and concentrated; the residue was purified directly by silica column chromatography (PE: EtOAc = 3: 1) to afford compound J-2. MS for J-2: m/e = 233 (M+l).

1260670-05-0 is used more and more widely, 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 belong naphthyridine compound,3-Bromo-1,7-naphthyridin-8(7H)-one,1375301-90-8,Molecular formula: C8H5BrN2O,mainly used in chemical industry, its synthesis route is as follows.,1375301-90-8

A mixture of compound E3 (2.0 g, 8.89 mmol), sodium methanolate (2.40 g, 44.4mmol) and copper(I) iodide (846 mg, 4.44 mmol) in DMF (20 mL) was stirred at 100 C for 16 hunder N2. Then mixture was concentrated to give cmde E4 which was used in the next stepwithout further purification.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-1,7-naphthyridin-8(7H)-one,belong naphthyridine compound

Reference£º
Patent; MERCK SHARP & DOHME CORP.; SCOTT, Jack, D.; BLIZZARD, Timothy, A.; WALSH, Shawn, P.; CUMMING, Jared, N.; (105 pag.)WO2017/95759; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,1,7-Naphthyridin-2(1H)-one,54920-82-0,Molecular formula: C8H6N2O,mainly used in chemical industry, its synthesis route is as follows.,54920-82-0

A suspension of the product of preparation 25 (423mg, 2.89mmol) in ethanol (10mL) was heated at 70¡ãC for 5 minutes, benzyl bromide (0.34ml, 2.89mmol) was then slowly added and the mixture was heated under reflux for 3 hours. The mixture was cooled to 0¡ãC and sodium borohydride (0.55g, 14.5mmol) was added. The mixture was stirred at 0¡ãC for 10 minutes and was then allowed to warm to room temperature. 6M hydrochloric acid (2mL) was carefully added and stirring continued at room temperature for 90 minutes. The resulting mixture was basified to pH 10 with 2M sodium hydroxide (10mL) and was partitioned between ethyl acetate (20mL) and water (10mL). The layers were separated and the aqueous was extracted with a dichloromethane/methanol mixture (95:5, 2x 20mL). The organic phases were combined, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid in 90percent yield, 626mg 1HNMR(CD3OD, 400MHz) delta: 2.62(m, 2H), 2.76(m, 2H), 3.42 (s, 2H), 3.71(s, 2H), 6.36(d, 1H), 7.26-7.41 (m, 6H) MS APCI+ m/z 241 [MH]+

With the synthetic route has been constantly updated, we look forward to future research findings about 1,7-Naphthyridin-2(1H)-one,belong naphthyridine compound

Reference£º
Patent; Pfizer Limited; EP1595881; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Step 1 To a stirred solution of intermediate D-7 (200 mg, 0.45 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (165 mg, 0.68 mmol) in THF (8 mL) was added LHMDS (1 M in THF, 1.13 mL, 1.13 mmol) at RT. The mixture was stirred at 45 C for 2 h, then an additional 1 eq. of LHMDS was added and the mixture was stirred at 45 C overnight. The mixture was diluted with saturated Nu0 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was rediluted with 5 mL of DCM and TFA (0.5 mL) was added. The resulting mixture was stirred at 25 C for 2 h, then neutralized with NaHC03, and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by prep-TLC (DCM: MeOH = 15 : 1) to afford compound L-1. MS for L-1 : m/e = 550 and 552 (M+l)., 1260670-05-0

With the rapid development 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 quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO378,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

To a solution of (R)-tert-butyl 3-(1,1-difluoro-4-iodobutyl)pyrrolidine-1-carboxylate (700 mg, 1.88 mmol) and 2-methyl-1,8-naphthyridine (407 mg, 2.82 mmol) in THF (12 mL) at 0¡ã C. was added LiHMDS (2.82 mL, 1M, 2.82 mmol). The reaction mixture was stirred at 0¡ã C. for 3 h, then quenched with saturated ammonium chloride solution (6 mL), diluted with water (15 mL) and extracted with EtOAc (30 mL¡Á2). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-TLC to give the desired product tert-butyl 3-(5-(1,8-naphthyridin-2-yl)pentyl)-3-fluoropyrrolidine-1-carboxylate as a light yellow solid (350 mg). Yield 48percent (ESI 388 (M+H)+).

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

Reference£º
Patent; Lazuli, Inc.; Harrison, Bryce A.; Bursavich, Matthew G.; Brewer, Mark; Gerasyuto, Aleksey I.; Hahn, Kristopher N.; Konze, Kyle D.; Lin, Fu-Yang; Lippa, Blaise S.; Lugovskoy, Alexey A.; Rogers, Bruce N.; Svensson, Mats A.; Troast, Dawn M.; (172 pag.)US2018/244648; (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.

0032-1 1,4-Dioxane (2 mL) and a 2 mol/L sodium carbonate aqueous solution (315 muL) were added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (77 mg), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)dichloropalladium(II) (15 mg) in a nitrogen atmosphere, and the reaction vessel was sealed, followed by stirring at 100 C. for 5 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), thereby obtaining 2-chloro-7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (57 mg) as a white solid. 1H-NMR (CDCl3) delta: 9.15 (1H, d, J=2.0 Hz), 8.35-8.31 (2H, m), 8.04 (1H, s), 8.00 (1H, s), 7.57 (1H, d, J=8.6 Hz), 5.53 (2H, s), 3.68-3.63 (2H, m), 0.99-0.93 (2H, m), 0.00 (9H, s)., 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