Heterocyclic Building Blocks-Naphthyridine

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

2-(2-((7-Methoxy-l,5-naphthyridin-4-yl)(methyl)amino)ethyl)-6-(4- methylthiophen-2-yl)pyridazin-3(2H)-one. A suspension of 2-(2- (methylamino)ethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (275 mg, 1103 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (193 mg, 993 mumol) in iPrOH (5 mL) was heated to 100 C for 18 h in an appropriately sealed vial. The mixture was partitioned between CH2Cl2 (30 mL) and IM NaOH (10 mL), and the organic dried over MgSO4. After concentration under reduced pressure, the organic residue was dissolved in iPrOH (2 mL) and the rsulting crystalized solid was washed with iPrOH (2x 0.5 mL) then dried under reduced pressure. MS (ESI pos. ion) m/z (MH+): 408. Calc’d exact mass for C2ieta2iN5O2S: 407. 1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H) 3.22 (s, 3 H) 3.83 (s, 3 H) 4.51 (t, J=5.77 Hz, 2 H) 4.75 (t, J=5.77 Hz, 2 H) 6.55 (d, J=5.52 Hz, 1 H) 6.60 (d, J=9.54 Hz, 1 H) 6.91 (s, 1 H) 6.97 (s, 1 H) 7.19 (d, J=9.54 Hz, 1 H) 7.32 (d, J=3.01 Hz, 1 H) 8.32 (d, J=5.52 Hz, 1 H) 8.46 (d, J=2.51 Hz, 1 H).

952059-69-7, 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.,952059-69-7 ,8-Chloro-3-methoxy-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
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.

To 50 mL of chloroform, 5.00 g of 3-bromo-1,5-naphthyridin was dissolved, 6.40 g of m-chloroperbenzoic acid was added thereto, and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, a 5% aqueous sodium thiosulfate solution and chloroform were added, and the organic layer was separated, washed sequentially with a 5% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of ethyl acetate:hexane = 1:1 to obtain 1.95 g of 3-bromo-1,5-naphthyridin-5-oxide as a light yellow solid. 1H-NMR (CDCl3) delta: 7.55 (1H, dd, J = 8.7, 6.0 Hz), 7.99 (1H, d, J = 8.7 Hz), 8.55 (1H, d, J = 6.0 Hz), 9.04 (1H, d, J = 2.3 Hz), 9.23 (1H, d, J = 2.3 Hz)

17965-71-8, 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.,17965-71-8 ,3-Bromo-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); 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.

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, 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.,7689-62-5 ,2-Chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

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

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.

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).

17965-71-8, 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.,17965-71-8 ,3-Bromo-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

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

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.

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.

952059-69-7, 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.,952059-69-7 ,8-Chloro-3-methoxy-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; AMGEN INC.; WO2008/124083; (2008); A2;,
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.

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)

100361-18-0, 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.,100361-18-0 ,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, other downstream synthetic routes, hurry up and to see

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 1,6-Naphthyridine-2-carboxylic acid, and cas is 197507-59-8, its synthesis route is as follows.

Triethylamine (3.03 ml, 21.8 mmol), ethyl chloroformate (3.73 ml, 39.0 mmol) and 4-dimethylaminopyridine (DMAP) (2.40 g, 19.6 mmol) are added, at O0C, to a solution of l,6-naphthyridine-2-carboxylic acid (138) (Chan, L., Jin, H., Stefanac, T., Lavallee, J.F., Falardeau, G., Wang, W., Bedard, J., May, S. and Yuen, L., J. Med. Chem., 1999, 42, 3023-3025) (1.00 g, 5.75 mmol) in anhydrous dichloromethane (75 ml). After returning to ambient temperature, the reaction mixture is brought to reflux for 5 hours, the solution is evaporated to dryness and then the residue is purified on a column of alumina eluted with ethyl acetate to result in the ester 139 (517 mg, 2.56 mmol). Yield: 45%; Rf: 0.86 (Al2O3, ethyl acetate); melting point: 106-1080C; 1H NMR (400 MHz, CDCl3) d 1.41 (t, 3H, J = 7 Hz), 4.49 (q, 2H, J= 7 Hz), 8.02 (d, IH, J= 6 Hz), 8.21 (d, IH, J= 8.5 Hz), 8.39 (d, IH, J = 8.5 Hz), 8.75 (d, IH, J = 6 Hz), 9.29 (s, IH); 13C NMR (100 MHz, CDCl3) d 14.3, 62.0, 122.4, 122.7, 124.0, 137.2, 147.5, 149.7, 152.3, 152.9, 164.6; IR (KBr) V cm”1 : 1256, 1734; MS (m/z, %) 202 (M+, 3), 158 (18), 130 (100), 102 (15), 75 (22), 51 (16).

197507-59-8, 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.,197507-59-8 ,1,6-Naphthyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); WO2008/12782; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

249889-68-7, 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-2-methoxy-1,5-naphthyridine, cas is 249889-68-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

The 2-[2-methoxy-4-(6-methoxy-l55~naphthyridm-4-yloxy)phenyl]acetic acid used as a5 starting material was prepared as follows :; -Under an atmosphere of argon, a mixture of 4-chloro-6-methoxy-l,5-naphthyridine (0.97 g), tert-bvLtyl 2-(4-hydroxy-2-methoxyphenyl)acetate (1.19 g), caesium carbonate (3.26 g) and DMF (10 ml) was stirred and heated to 13O0C for 3.5 hours. The resultant mixture was cooled to ambient temperature and partitioned between ethyl acetate and water.I0 The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether and ethyl acetate as eluent. There was thus obtained tert-bxxtyl 2-[2-methoxy- 4-(6-methoxy-l,5-naphthyridin-4-yloxy)phenyl]acetate (1.22 g); 1H NMR Spectrum: (DMSOd6) 1.41 (s, 9H)5 3.51 (s, 2H), 3.75 (s, 3H)5 3.94 (s, 3H)5 6.71 (m5 IH), 6.92 (m, 2H)5 is 7.24 (d5 IH)5 7.29 (d, IH)5 8.27 (d5 IH)5 8.61 (d, IH).

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-2-methoxy-1,5-naphthyridine, 249889-68-7

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, 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. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A suspension of (6) (10 g) in 29 mL of 12% HCl and 26 mL of glacial acetic acid was refluxed for 7.5 h. It was cooled, filtered and recrystallized from a boiling mixture of methanol and acetone to yield 6.3 g of (7) m.p.=195-200 C.

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 Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, 100491-29-0

Reference£º
Patent; Vymed Corporation; SHETTY, B. Vithal; US2014/73631; (2014); 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.

Method A B-9 Ex. 21 To a stirred solution of Intermediate B-9 (99.0 mg, 0.231 mmol) and 8-chloro-3-methoxy- 1 ,5-naphthyridine (30.0 mg, 0.154 mmol) in THF (4 ml) under nitrogen was added chloro[2- (dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-triisopropyl-l ,l ‘-biphenyl][2-(2- aminoethyl)phenyl]palladium(II) (24.6 mg, 0.0310 mmol) and sodium teri-butoxide (0.154 mL, 2 M) at RT. The mixture was stirred at 40 C for 15 h, cooled, filtered, and diluted with water (5 ml) and extracted with EtOAc (6 mL x 3). The organic layers were collected, dried with sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM (6 mL), treated with TFA (0.200 mL) and stirred at 18 C for 1 h. The mixture was quenched with aqueous sodium hydrogen carbonate (5 ml) and extracted with EtOAc (5 mL x 4). The combined organic extracts were washed with brine, dried (Na2S04), filtered and concentrated. The residue was purified by prep-HPLC (column 250 x 21.2 mm, 4 muiotaeta; mobile phases A = 0.075 % TFA water, B = MeCN; gradient 10-40% B, 11 min, 25 mL/min) to provide example 21. MS for example 21: m/e = 485 (M+l).

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; 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