Heterocyclic Building Blocks-Naphthyridine

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.

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.

1260670-05-0, 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.,1260670-05-0 ,3-Bromo-8-chloro-1,7-naphthyridine, other downstream synthetic routes, hurry up and to see

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

Name is 2,7-Naphthyridin-1-amine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 27225-00-9, its synthesis route is as follows.

4-Bromo-2,7-naphthyridin-1-ylamine32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25% aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

27225-00-9, 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.,27225-00-9 ,2,7-Naphthyridin-1-amine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Merck Patent GmbH; Jonczyk, Alfred; Zenke, Frank T.; Amendt, Christiane; US2015/252041; (2015); 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. Method I: 560 mg (5mmol) of 1,4-diazabicyclo[2.2.2]octane and 890 mg (5.3 mmol) of 90% pure 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole are added to 1.9 g (5 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate in 20 ml of acetonitrile. The mixture is stirred at room temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 80 ml of water. The undissolved residue is filtered off with suction, washed with water and dried. Yield: 1.6 g (64% of theory) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylate, melting point: 173-176 C. (with decomposition)

The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Bayer Aktiengesellschaft; US5464796; (1995); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100361-18-0, 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. 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 Synthesis of (R,S)-7-(3-Aminomethyl-4-syn-methoxyimino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid triethylamine (5.1 ml) was added to 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (3.05 g) in water (25 ml) at 15-20 C. and the mixture stirred for 20 min. 4-Aminomethyl-3-methoxyimino-pyrrolidinium dimethanesulfonate (3.86 g) was added, followed by water (5 ml), and the mixture stirred at 20-25 C. for 173/4 hours.. The resulting product was filtered and the cake washed with water (30 ml) followed by ethanol (30 ml) and dried under vacuum at 50 C. to give the title compound as a white solid (4.23 g).. (102% as is, 86% on assay).. Characterising data were consistent with a standard sample of the title compound.

The chemical industry reduces the impact on the environment during synthesis,100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; SB Pharmco Puerto Rico Inc. of the United States Corporation Company; US6703512; (2004); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 5,7-Dichloro-1,6-naphthyridine, and cas is 337958-60-8, its synthesis route is as follows.

To 5,7-dichloro-1 ,6-naphthyridine (5.01 g, 25.2mmol) and 1 , 1 -dimethylethyl (3R)-3- (aminomethyl)-3-fluoro-1 -piperidinecarboxylate (5.32g, 22.90mmol) in NMP (20ml) was added DI PEA (8.00ml, 45.8mmol) and the mixture was stirred at 100C for 72h under nitrogen. The reaction was cooled and partitioned between ethyl acetate and water (200ml each). The aqueous was washed with ethyl acetate. The combined organics were washed with water and the solvent was removed. The residue was dissolved in DCM and loaded onto a 100g silica SNAP column and purified on the SP4 eluting with 0-50% ethyl acetate in cyclohexane over 17CVs. Appropriate fractions were combined and the solvent was removed to give the title compound as a pale orange solid which was dried under high vacuum for 2h (7.61 g).LCMS (Method B): Rt = 1 .12min, MH+ 395/397

337958-60-8, 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.,337958-60-8 ,5,7-Dichloro-1,6-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander George Steven; WILSON, David Matthew; WO2011/134971; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100361-18-0, 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. 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolidine dimethanesulfonate (12. 5g), 2-hydroxybenzaldehyde (8.6g) and triethylamine (12.2g) were in turn introduced into a reaction vessel at room temperature. After stirring the mixture for about 0. 5h, 7- chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8- naphthyridine-3-carboxylic acid (lO. Og) was introduced thereto. The resultant reaction mixture was stirred for about 15h at room temperature, cooled to O~ 5 C, and stirred for about 3h. The title compound in the form of solid was filtered, washed with acetonitrile, and dried to prepare 16.0 g of the title compound (Yield: 91. 8%). ‘H NMR (6, CDC13) : 8. 68 (s, 1H), 8.42 (s, 1H), 8.01 (d, J=12.4Hz, 1H), 7. 30-7. 20 (m, 3H), 6. 90-6. 82 (m, 2H), 4. 68-4. 53 (m, 2H), 4. 32-4. 24 (m, 1H), 4.06 (dd, J1=11. 9Hz, J2=5. 5Hz, 1H), 4. 02-3. 85 (m, 3H), 3.95 (s, 3H), 3.60 (m, 1H), 3.40 (m, 1H), 1. 29-1. 21 (m, 2H), 1. 07-1. 00 (m, 2H) Mass (FAB): 494 (M+H)

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 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, 100361-18-0

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2003/87100; (2003); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2,7-Naphthyridine-4-carbaldehyde, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 10273-40-2, its synthesis route is as follows.

General procedure: To an indole-3-acetonitrile derivative (1.0 equiv) dissolved in anhydrous methanol (4mL for 2.31mmol of starting material) in a dried microwave vial, sodium methoxide (1.7 equiv) was added and stirred at room temperature for 15min protected from light. Quinoline/isoquinoline-carboxaldehyde derivative (1.2 equiv) was added and the mixture was subjected to microwave irradiation at 95C for 8.5min. The reaction was cooled to room temperature and then chilled in an ice/salt bath. The resulting precipitate was filtered, washed with methanol, and dried under vacuum to afford a solid as the product.

10273-40-2, 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.,10273-40-2 ,2,7-Naphthyridine-4-carbaldehyde, other downstream synthetic routes, hurry up and to see

Reference£º
Article; See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 344 – 367;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 4-Chloro-1,8-naphthyridine, and cas is 35170-94-6, its synthesis route is as follows.

To a solution of 0.5 g (3.04 mmol) of 4-chloro-[1,8]naphthyridine in 10 mL of DMF was added 0.39 g (6.08 mmol) of NaN3. The mixture was stirred for 5 h at 60C. The reaction was allowed to cool to roomtemperature and diluted with 300 ml. of EtOAc, washed with water, brine and dried over Na2SO4. The desiccant was filtered off and the solvents were evaporated under vacuum to give 0.5 g of 4-azido-1,8- naphthyridine as a light brown solid.To a solution of 0.5 g (2.92 mmol) of 4-azido-1,8-naphthyridine in 30 mL of THF was added 100mg of 10% Pd/C. The mixture was hydrogenated at 30C under atmospheric pressure for 5 h. The catalyst wasremoved by filtration. The solvent was evaporated to give 420 mg of 1 ,8-naphthyridin-4-amine a crude product as a light brown solid.To a solution of 0.42 g (2.89 mmol) of 1,8-naphthyridin-4-amine in 50 mL of DCM were added 0.64 g (2.89 mmol) of Boc2O, 0.11 g (0.87 mmol) of DMAP and 1.43 mL (8.68 mmol) of DIPEA and then the mixture was stirred at 30C for 16 h. The solvent was removed under vacuum and the residue waspurified by column chromatography eluting with DCM/MeOH (20/1, R1= 0.4) to give 350mg of tertbutyl N-(1 ,8-naphthyridin-4-yl)carbamate as a brown solid.A suspension of 280mg (1.14 mmol) of tert-butylN-(1,8-naphthyridin-4-yl)carbamate and 164 mg (0.12 mmol) of NaH in 2 ml. of THF was stirred at 40C for 16 h. A solution of 0.04 g (0.13 mmol) of 4- bromo-6-(bromomethyl)isoquinoline in 2 mL of THF was added thereto at 3 5C. The mixture was stirredat 35C for additional 0.5 h. The reaction was quenched with saturated aqueous NH4C1 solution. The mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the product as a light brown semisolid which was purified by preparative HPLC to give 140 mg of tert-butyl N-[l- [(4-bromo-6-isoquinolyl)methyl] -1, 8-naphthyridin- 1 -ium-4- yl]carbamate as a light brown solid.MS (+ESI): 465.0, 467.0 [M+H].?H NMR (400 MHz, DMSO-d6+ D20) ppm: 9.23 (s, 1H), 9.04 (m, 2H), 8.68 (s, 1H), 8.25 (d, J 8.0 Hz, 1H), 8.13 (d, J= 8.8 Hz, 1H), 7.94 (s, 1H), 7.66 (m, 2H), 7.55 (d, J= 4.8 Hz, 1H), 5.25 (br s, 2H), 1.27 (s, 9H).

35170-94-6, 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.,35170-94-6 ,4-Chloro-1,8-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 7-Chloro-1,8-naphthyridin-2-ol, cas is 15944-34-0 its synthesis route is as follows.

EXAMPLESEXAMPLE l7-(4-Hydroxy-butoxy)-lH-[l,8]naphthyridin-2-one; To 1 liter (L) of n-methylpyrrolidinone was added 60% sodium hydride suspension (83.6g, 2.09moles). With external cooling to maintain 50C, 1,4-butanediol (3.39 moles) was added dropwise, causing offgassing. The mixture was stirred for 15 minutes at 60C, followed by addition of 7-Chloro-lH-[l,8]naphthyridin-2-one (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 146g, 0.813 moles) while stirring at 680C for 20 hours (h). To the mixture was added 5 liters of acetonitrile followed by filtration of a solid which was washed with a 50:50 mixture of acetonitrile and tetrahydrofuran. The solid was resuspended in 3 liters of tetrahydrofuran, to which was EPO added 3N HCl in methanol (290ml, 0.870 moles). After heating for 1 hour at 6O0C, the mixture was filtered thru celite, washed with 1 liter of tetrahydrofuran and concentrated to 500ml in volume. To the residue was added 1.5 liters of tetrahydrofuran, 1Og Darco activated charcoal, and 100ml Magnesol. After stirring at 40C for 30 minutes (min.), the mixture was filtered and washed with tetrahydrofuran and concentrated to 500ml in volume. To this residue was added 1 liter of acetonitrile followed by concentration of the mixture to 1 liter in volume. The resulting solid precipitate was filtered, washed with acetonitrile and ether, and dried at 50C giving 7-(4-Hydroxy-butoxy)-lH- [l,8]naphthyridin-2-one, 101g, (53% yield).

15944-34-0, 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.,15944-34-0 ,7-Chloro-1,8-naphthyridin-2-ol, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Description 94; 6-(1 8-Naphthyridin-2-yl) pvrimidin-4-amine; To a mixture of Description 92 (2.52 g, 15. 3 mmol), hexamethylditin (5.0 g, 15.3 mmol), lithium chloride (1.95 g, 45.9 mmol), and copper (I) iodide (291 mg, 1.53 mmol) in anhydrous 1,4-dioxane (50 ml) was added Pd (PPh3) 4 (884 g, 0.77 mmol). The mixture was de-gassed three times, and heated at 100C overnight. The mixture was cooled and diluted with EtOAc (120 ml) and washed with a 10% potassium fluoride solution (200 ml). The organic layer was washed with sat. NaCl (50 ml), dried over Na2SO4, filtered, and evaporated. The residue was taken up in anhydrous 1,4-dioxane (75 ml), and Description 93 (1.55 g, 7 mmol), lithium chloride (1.78 g, 42 mmol), and copper (I) iodide (266 mg, 1.4 mmol) added, followed by Pd (PPh3) 4 (808 mg, 0.7 mmol). The mixture was de-gassed 3 times and heated at 100C for 3 days. The mixture was poured into water (200 ml), and extracted with EtOAc (2 x 100 ml), the combined EtOAc layers were washed with water (150 ml), sat. NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica (eluent: 2% MeOH in DCM + 0.5% NH40H) to give the title compound (100 mg, 3%).’H NMR (360 MHz, DMSO-d6) 7.18 (2 H, br s), 7.66-7. 86 (3 H, m), 8.55 (1 H, dd, J 8.1 and 1. 8), 8. 58 (1 H, d, J4. 2), 8.64 (1 H, d, J8. 4), 9.16 (1 H, dd, J4. 2 and 2.1).

15936-10-4, 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.,15936-10-4 ,2-Chloro-1,8-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem