Month: March 2021

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 6-Bromo-1,8-naphthyridin-2-ol, and cas is 72754-05-3, its synthesis route is as follows.

Step 1: A mixture of 6-bromo-i,8-naphthyridin-2(1H)-one (1.0 equiv) and 2,5-dihydrofuran (10 equiv) in AcOH (0.05 M) was irradiated with UVA lamps (Rayonet reactor, RPR3 500 A bulbs) at RT overnight. The mixture was filtered, washing with EtOAc, and the solids were dried in vacuo. The so-obtained residue was purified via flash chromatography over silica gel, eluting with DCM and 0-20% EtOAc gradient to provide the title (rac)-2-bromo- 6a,6b,7,9,9a,9b-hexahydrofuro[3 ?,4?: 3 ,4]cyclobuta[ 1,2-c] [1 ,8]naphthyridin-6(5H)-one as a yellow solid in 9% yield. ?H NIVIR (400 IVIHz, DMSO-d6) oe 10.60 (s, 1H), 8.20 (m, 1H), 7.85 (m, 1H), 4.13 (d,J= 9.4 Hz, 1H), 3.97 (d,J= 9.6 Hz, 1H), 3.38 (m, 3H), 3.06 (d,J 8.9, 5.1 Hz, 1H), 2.90 (dd, J= 9.7, 4.4 Hz, 1H), 2.84 (m, 1H). LCMS (m/z) (M+H) = 295.1/297.1, Rt = 0.69 mm.

72754-05-3, 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.,72754-05-3 ,6-Bromo-1,8-naphthyridin-2-ol, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Bromo-2-chloro-1,5-naphthyridine, and cas is 1309774-03-5, its synthesis route is as follows.

A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino-l,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]

1309774-03-5, 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.,1309774-03-5 ,7-Bromo-2-chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

Step 1: 3-bromo-N-(2-methylbiphenyl-3-yl)-1, 7-naphthyridin-8-amine To a microwave vial was added 2-methylbiphenyl-3-amine (Example 1, Step 1: 0.1 g, 0.546 mmol), 3-bromo-8-chloro-1,7-naphthyridine (PharmaBlock, cat#PBLJ2743: 140 mg, 0.55 mmol), tert-butyl alcohol (2.5 mL) and 4.0 M hydrogen chloride in dioxane (0.136 mL, 0.546 mmol). The resulting mixture was irradiated in the microwave to 100 C. for 1 h. The resulting mixture was concentrated, and the desired product was used directly in the next step. LC-MS calculated for C21H17N3Br (M+H)+: m/z=390.1; found 390.1.

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; Lajkiewicz, Neil; Wu, Liangxing; Yao, Wenqing; (58 pag.)US2017/174679; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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 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).

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 3-Bromo-8-chloro-1,7-naphthyridine, 1260670-05-0

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

1309774-03-5, 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-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

0393-3 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (80 mg), 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (231 mg), sodium carbonate (87 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (23 mg), water (0.3 mL), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 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-hexane), thereby obtaining 7-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-pyrazol-4-yl)-2-chloro-1,5-naphthyridine (76 mg). MS m/z (M+H): 389.

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-Bromo-2-chloro-1,5-naphthyridine, 1309774-03-5

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

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.

General procedure: (Method C1) Synthesis of N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine A 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-1-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-1,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150 C. 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-1-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; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

96568-07-9, 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-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 96568-07-9,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Example 109 7-(4-chloro-2-isoindolinyl)-1-cyclopropyl-6-flurro-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid STR325 310 mg of 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4- oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 660 mg of 4-chloroisoindoline, 0.42 ml of triethylamine, and 5 ml of anhydrous chloroform were processed in the same manner as in Example 107 to produce 75 mg of 7-(4-chloro-2- isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8- naphthyridine-3-carboxylic acid. Melting point: above 300 C. 1 H-NMR (DMSO-d6) delta: 8.68 (1H, s, C2 –H), 8.06 (1H, d, C5 –H), 7.45-7.55 (3H, m, ARM-H), 5.3 (4H, br, s, 2 x–CH2 N–), 3.83 (1H. m, STR326 1.10-1.40 (4H, m, STR327

The chemical industry reduces the impact on the environment during synthesis,96568-07-9,Ethyl 7-chloro-1-cyclopropyl-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; Wakunaga Seiyaku Kabushiki Kaisha; US5026856; (1991); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem