Heterocyclic Building Blocks-Naphthyridine

1260670-05-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Step 1 To a stirred solution of intermediate A-10 (1.43 g, 3.36 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (0.982 g, 4.03 mmol) in THF (34 ml) was added LHMDS in THF (11.8 ml, 11.8 mmol) at RT. The mixture was stirred at 45 C for 14 h, cooled, and diluted with dichloromethane (200 mL) and water (50 ml). The organic layers were collected, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (120 g of Si02> 0-100% EtOAc in hexane) to provide example 17. MS for example 17: m/e = 532 and 534 (M+l).

The chemical industry reduces the impact on the environment during synthesis,1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,I believe this compound will play a more active role in future production and life.

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

Name is 1,7-Naphthyridin-2(1H)-one, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 54920-82-0, its synthesis route is as follows.

To 1,7-naphthyridine-2(1H)-one (CAS registration No.: 54920-82-0) (900 mg), ethanol (20 mL) and benzylbromide (0.8 mL) were added. The resulting mixture was heated and stirred at 80¡ãC for 18 hours. The resulting mixturewas cooled to 0¡ãC, and then sodium borohydride (1100 mg) was added thereto. The resulting product was stirred at0¡ãC for 10 minutes, and then hydrochloric acid was added thereto. The resulting mixture was stirred at room temperaturefor 90 minutes. The resulting product mixture was neutralized with sodium hydroxide, and then ethyl acetate was addedto extract the organic layer. The organic layer was extracted. The organic layer was washed with a saturated salinesolution, and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reducedpressure. Thereafter, the resulting solid was washed with ethyl acetate to obtain the title compound (900 mg) havingthe following physical property values.1H-NMR (CD3OD): delta 2.66, 2.80, 3.45, 3.75, 6.40, 7.29-7.44

54920-82-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,54920-82-0 ,1,7-Naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; ONO Pharmaceutical Co., Ltd.; INUKAI, Takayuki; TAKEUCHI, Jun; YASUHIRO, Tomoko; WOLF, Mark Allan; PAWAR, Vijay Dattaram; CHAKRABARTI, Anjan; CHITTIMALLA, Santhosh Kumar; (85 pag.)EP3067356; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Example 41 (Method C5)Synthesis of N-(6-(7-methoxy-l,5-naphthyridin-4-yloxy)pyridin-3-yl)-4- phenylphthalazin-l-amine A pyrex reaction tube was charged with 8-chloro-3-methoxy-l ,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-l-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 0C. 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, basifed 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 CH2Cl2MeOHZNH4OH. This provided N-(6-(7-methoxy-l,5-naphthyridin-4- yloxy)pyridin-3-yl)-4-phenylphthalazin-l -amine as pure material. MS [M+H] = 473.01.48minutes. Calc’d for C28H20N6O2: 472.5.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 8-Chloro-3-methoxy-1,5-naphthyridine, 952059-69-7

Reference£º
Patent; AMGEN INC.; WO2008/124083; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Under an atmosphere of argon, a mixture of 4-chloro-7-methoxy-l,5-naphthyridine (1 g), methyl 2-(4-hydroxy-2-methoxyphenyl)acetate (1.01 g), caesium carbonate (5.02 g) and DMF (10 ml) was stirred and heated to 1000C for 3 hours. The resultant mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate and methanol as eluent. There was thus obtained methyl 2-[2-methoxy-4-(7-methoxy-l,5-naphthyridin- 4-yloxy)phenyl]acetate (1.23 g); 1H NMR Spectrum: (DMSOd6) 3.63 (s, 3H)5 3.65 (s, 2H)5 3.76 (S5 3H)5 4.0 (s, 3H)5 6.75 (m, 2H), 6.95 (d, IH), 7.3 (d, IH), 7.79 (d, IH)5 8.72 (m, 2H); Mass Spectrum: M+H+ 355.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 8-Chloro-3-methoxy-1,5-naphthyridine, 952059-69-7

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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.

The compound obtained from the preparation example 10 (4.44 g), 1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8] naphthyridine-3-carboxylic acid (3.45 g), and triethylamine (2.6 in,) were added to acetonitrile (50 ml) in order and the reaction mixture was sitirred at 4550 C. for 4 hr. The precipitate was filtered and dried to obtain the desired compound (5.31 g, 77.6%). [00102] 1H-NMR(CDCl3, ppm) 0.80 (3H, s), 1.07 (2H, bs), 1.17 (3H, s), 1.24 (5H, bs), 1.26 (2H, bs), 1.41 (9H, s), 3.40 (2H, bs), 3.553.60 (5H, m), 4.054.32 (4H, m), 5.07 (1H, bs), 8.03 (1H, d, J=12.4 Hz), 8.71 (1H, s); [alpha]D=+9.77 (c=1.19, CHCl3, 25.0 C.)., 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; Dong Wha Pharm. Ind. Co., Ltd.; US6649763; (2003); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

7-Bromo-1,5-naphthyridine-1-oxide (6) To a stirring solutionof compound 5 (100 mg, 0.48 mmol) in3 mL CH2Cl2 at 0C was added m-CPBA (142 mg, 0.58 mmol) in portion for 5 min, then at roomtemperature for 2 h. Water (10 mL) was added to quench the reaction, and themixture was extracted with CH2Cl2 (3¡Á10 mL). Thecombined extracts were washed with brine, dried over anhydrous Na2SO4,and concentrated in vacuum. Purification by chromatography (PE/EA = 2:1)provided compound 6 (64 mg, 67%) asa white solid. MP: 151~152C (Ref.2 148~149C). 1H NMR(400 MHz, CDCl3): delta9.26-9.13 (m, 1H), 9.00 (dd, J = 4.7,2.3 Hz, 1H), 8.54 (d, J = 5.8 Hz, 1H),7.98 (d, J = 6.1 Hz, 1H), 7.54 (dd, J = 9.2, 5.2 Hz, 1H).

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

Reference£º
Article; Wu, Jing-Fang; Liu, Ming-Ming; Huang, Shao-Xu; Wang, Yang; Bioorganic and Medicinal Chemistry Letters; vol. 25; 16; (2015); p. 3251 – 3255;,
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.100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.

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., 100491-29-0

As the paragraph descriping shows that 100491-29-0 is playing an increasingly important role.

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Chloro-1,8-naphthyridine, and cas is 15936-10-4, its synthesis route is as follows.,15936-10-4

EXAMPLE 2 Preparation of 2-(4-(1,8-naphthyridin-2-yloxy)phenoxy)propanoic acid STR9 A 3-necked flask was equipped with a thermometer, a magnetic stirrer, a reflux condenser and a nitrogen line and flushed with nitrogen. The flask was charged with 15 ml of hexane and 1.38 gm (28.8 m moles) of 50% NaH/oil dispersion. After stirring for 10 minutes the hexane was decanted and replaced with 5 ml of DMSO followed by the dropwise addition of a solution of 2.18 gm (12 m moles) of 2-(4-hydroxyphenoxy)propanoic acid in 5 ml of DMSO. The mixture was warmed to 60 C. and a solution of 1.97 gm of 2-chloro-1,8-naphthyridine in 10 ml of DMSO was added. After warming the reaction mixture at 95 C. for one hour, the mixture was cooled to room temperature and water cautiously added. The solution was extracted with methylene chloride and the aqueous phase neutralized with acetic acid to give a white precipitate. The aqueous mixture was extracted with CH2 Cl2 and the organic layer washed twice with water, dried over Na2 SO4 and evaporated to dryness to give 3.3 gm of yellow solid which could not be redissolved in ether or CH2 Cl2.

With the complex challenges of chemical substances, we look forward to future research findings about 15936-10-4,belong naphthyridine compound

Reference£º
Patent; The Dow Chemical Company; US4472193; (1984); A;,
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: C8H14ClNO62,mainly used in chemical industry, its synthesis route is as follows.,1375301-90-8

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-1,7-naphthyridin-8(7H)-one,belong naphthyridine compound

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

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

Example 37 (Method Cl); Synthesis of N-(4-(7-methoxy-l ,5-naphthyridin-4-yloxy)phenyl)-4-(4- methoxyphenyl)phthalazin-l-amineA 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-l- ylamino)phenol and 3 equivalents of cesium carbonate (342 mg, 1.048 mmol) in 1.8 mL of DMF. The mixture was stirred at RT for 10 min. Following addition of 8-chloro-3- methoxy-l,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150 0C for 15 min in the microwave, at which time the reaction was determined complete by LC/MS. The mixture was cooled to ambient temperature and diluted with water. The solids were filtered and washed with water. The solids were triturated with methanol, filtered to remove remaining impurities, washed with additional methanol and dried under vacuum to afford N-(4-(7-methoxy- 1 ,5-naphthyridin-4-yloxy)phenyl)-4-(4- methoxyphenyl)phthalazin-l -amine as a light orange solid. MS [M+H]=502; Calc’d 501.54 for C30H25N5O3.

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.; WO2008/124083; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem