Heterocyclic Building Blocks-Naphthyridine

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.

1260670-05-0, [(R)-5-(5-Amino-2-fluoro-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1 ,4] oxazin-3-yl]-carbamic acid tert-butyl ester (CAS registry 1262859-09-5) (250 mg, 0.696 mmol) and 3-bromo-8- chloro-[1 ,7]naphthyridine [Heteroaryl 1] (186 mg, 0.765 mmol) were dissolved in tert-Butanol (4 ml) in a microwave vial and HCI (0.174 ml of a 4M solution in dioxane) was added. The vial was sealed and heated to 100 C for 1 h. The reaction mixture was cooled to rt and added to a saturated NaHC03 solution (20 ml) and stirred at rt for 10 min.The solution was extracted with DCM (2 x 30 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04, filtered and to give the desired product. HPLC: RtH9= 0.90 min; ESIMS [M+H]+ = 465.9/467.9(1 Br);1H-NMR (400 MHz, CDCI3): delta 8.90 (s, 1 H), 8.64 (m, 1 H), 8.27 (m, 1 H), 8.08 (d, 1 H), 7.90 (dd, 1 H), 7.10 (dd, 1 H), 6.82 (d, 1 H), 6.34-6.06 (t, 1 H), 4.35 (dd, 1 H), 4.18 (d, 1 H), 4.07 (d, 1 H), 3.96 (d, 1 H).19F-NMR (376 MHz, CDCI3): delta – 1 19.6 (s), (- 126.53) – (- 129.20) (dq).

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; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is Ethyl 7-chloro-1-cyclopropyl-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 96568-07-9, its synthesis route is as follows.,96568-07-9

EXAMPLE 52 Ethyl (1’RS,2’RS,6’RS)-1-cyclopropyl-7-(2′-ethyloxycarbonylaminomethyl-8′-azabicyclo[4.3.0]non-4′-en-8′-yl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate STR192 A mixture consisting of 828 mg (2.6 mmol) of ethyl 7-chloro -1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, 900 mg (4 mmol) of the product from Example K and 20 ml of acetonitrile is stirred at room temperature for three days. Subsequently, insoluble components are filtered off with suction and the solution is concentrated in vacuo. The crude product is purified by chromatography (eluent: dichloromethane/ methanol/conc. ammonia 15:4:0.5). Yield: 700 mg (56% of theory). 1 H-NMR (DMSO-d3): 8.36 (s, 1H, 2-H); 7.81 (d, 1H, 5-H); 7.21 (t, 1H, carbamate-NH); 5.73; 5.67 (2m, 2x 1H, HC=CH); 4.20; 3.99 (2q, 2x 2H, 2x ethyl-CH2); 3.86 (m, 1H); 3.78 (m, 1H); 3.56 (m, 2H); 3.13-3.01 (m, 2H); 2.89 (m, 1H); 2.35 (m, 1H); 2.18 (m, 2H); 1.88 (m, 2H); 1.26;-1.19 (2t, 2x 3H, 2x ethyl-CH3); 1.02; 0.88 ppm (2x H, 4x cyclopropyl-H).

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Patent; Bayer Aktiengesellschaft; US5556979; (1996); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1309774-03-5

Example 0762 0762-1 60% sodium hydride (136 mg) was added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (300 mg), (4-methoxyphenyl)methanol, and N-methylpyrrolidone (12.3 mL) at a temperature of from 0 C. to 5 C., followed by stirring at room temperature for 2 hours in a nitrogen atmosphere. After water and ethyl acetate were added to the reaction mixture, the organic layer was washed sequentially with 0.01 mol/L hydrochloric acid and 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 (ethyl acetate-hexane), thereby obtaining 7-bromo-2-((4-methoxybenzyl)oxy)-1,5-naphthyridine (204 mg) as a white solid. MS m/z (M+H): 345.

As the paragraph descriping shows that 1309774-03-5 is playing an increasingly important role.

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

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.

1309774-03-5, 0385-7 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (142 mg), bis(pinacolato)diboron (223 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (47 mg), potassium acetate (115 mg), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(3-(3-ethyl-4-iodo-1H-pyrazol-1-yl)propyl)morpholine (204 mg), sodium carbonate (124 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (41 mg), and water (0.3 mL) were added thereto, followed by stirring at 80 C. for 4 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, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-ethyl-1H-pyrazol-1-yl)propyl)morpholine (18 mg). MS m/z (M+H): 386.

1309774-03-5 is used more and more widely, 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

1260670-05-0, 3-Bromo-8-chloro-1,7-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1260670-05-0

A mixture of 3-bromo-8-chloro-1,7-naphthyridine (PharmaBlock catPBLJ2743: 0.200 g, 0.821 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (Aldrich cat663348: 153 muL, 0.904 mmol), sodium carbonate (0.174 g, 1.64 mmol) and [1,1?-bis(dicyclohexylphosphino)ferrocene]dichloropalladium( II) (Aldrich cat701998: 6.2 mg, 0.0082 mmol) in tert-butyl alcohol (5.91 mL, 61.8 mmol) and water (6 mL, 300 mmol) was degassed and sealed. It was stirred at 110 C. for 2 h. The reaction mixture was cooled to room temperature then extracted with ethyl acetate (3¡Á20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was used directly in the next step without further purification. LC-MS calculated for C10H8ClN2 (M+H)+: m/z=191.0; found 191.0.

The synthetic route of 1260670-05-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); 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.

REFERENCE EXAMPLE 2 Synthesis of 7-(3-aminomethyl-4-methoxyimino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[1,8]-naphthyridine-carboxylic acid (9) 141 mg (0.5 mmole) of 1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid and 108 mg (0.5 mmole) of 3-aminomethylpyrrolidin-4-one O-methyloxime dihydrochloride were added to 2.5 ml of dry acetonitrile. Then, 230 mg (1.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene was slowly added dropwise thereto and the mixture was heated for 0.5 hour and then cooled down to room temperature. 1 ml of distilled water was added to the reaction solution. The precipitated solid was separated and dried to obtain 167 mg (Yield: 85%) of the title compound., 100361-18-0

100361-18-0 is used more and more widely, 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; LG Chemical, LTD; US6307059; (2001); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: 2-Chloromethyl-1,8-naphthyridine A solution of 2-methyl-1,8-naphthyridine (Chem. Pharm. Bull., 19, 1857 (1971)), N-chlorosuccinimide (1.1 equivalent), and a catalytic amount of benzoylperoxide in CCl4 were irradiated at reflux with a 225 watt lamp for 5 hours. After cooling, the solid was filtered and the filtrate evaporated to dryness. The crude residue was chromatographed to give the title product., 1569-16-0

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; Merck Frosst Canada Inc.; US5273980; (1993); A;,
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.

General procedure: Parallel preparation of examples 6-7: To a set of vials containing the requisite aryl halide (0.20 mmol) was added a solution of HI (50 mg, 0.10 mmol) in THF (1.0 mL). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF, 0.25 mL, 0.25 mmol). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vial was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added water (0.050 mL) and TFA (0.5 mL). The mixtures were stirred at 50C with stirring overnight. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude residue containing Example 6 was purified by mass triggered preparative HPLC. [column: Waters XBridge CI 8, 5mupiiota , 19×100 mm; solvent: gradient 35-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Example 6. The crude residue containing Example 7 was purified by mass triggered preparative HPLC [Waters Sunfire CI 8 column, 5muetaiota, 19 100 mm, using a gradient from 10% initial to 45% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 min run time] to afford Example 7., 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.; CUMMING, Jared, N.; SCOTT, Jack, D.; (65 pag.)WO2016/40226; (2016); 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.

0031-1 A mixture solution of 7-bromo-2-chloro-1,5-naphthyridine (100 mg) in 1,4-dioxane (2 mL) and a 25% ammonia aqueous solution was stirred at 120 C. for 3 hours using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and a saturated sodium chloride aqueous solution and ethyl acetate were added thereto. The organic layer was collected by separation, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 7-bromo-1,5-naphthyridine-2-amine (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.0 (1H, d), 7.9 (1H, d), 7.0 (1H, d), 6.9 (1H, s). MS m/z (M+H): 224, 226., 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

96568-07-9, Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,96568-07-9

(1) A mixture of 310 mg of 1-cyclopropyl-6-fluoro-7- chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 745 mg of 5-acetamidomethylisoindoline, 0.56 ml of triethylamine, and 5 ml of anhydrous chloroform was heated at 60-70 C. for 0.5 hours while stirring. The resulting reaction mixture was diluted with 25 ml of chloroform. The mixture was washed with 5% acetic acid and brine in this order, dried over anhydrous sodium sulfate, and condensed. The residue was crystallized by the addition of ethylether. The crystals were collected by filtration and recrystallized from a mixed solvent of chloroform, methanol, and ethanol to obtain 260 mg of 7-(5- acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester.

As the paragraph descriping shows that 96568-07-9 is playing an increasingly important role.

Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5026856; (1991); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem