Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows., Author tianliPosted on September 25, 2020Categories 72754-05-3, naphthyridineTags M.W:200-300

10261-82-2, 1,5-Naphthyridin-2(1H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,10261-82-2

A 250 mL round bottomed flask charged with 1,5-naphthyridin-2(1H)-one (2.98 g, 20.37 mmol) and phosphorus oxychloride (40 ml, 437 mmol) was heated at 100 C. for 3 h. The reaction was cooled to room temperature and excess POCl3 was removed in vacuo. The re

10261-82-2 1,5-Naphthyridin-2(1H)-one 589680, anaphthyridine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.249889-68-7,8-Chloro-2-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows., Author tianliPosted on September 25, 2020Categories 249889-68-7, naphthyridineTags M.W:100-200

54920-82-0, 1,7-Naphthyridin-2(1H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,54920-82-0

As the paragraph descriping shows that 54920-82-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

To a solution of 2-methyl-1 ,8-naphthyridine (3.0 g, 20.7 mmol) in CH2CI2 (300 ml) was added Lambda/-chlorosuccimide (11.1 g, 81.6 mmol) and AIBN (15 mg). The reaction was refluxed for 4h with additional AlBN (7mg) added each hour, followed by reflux for 3Oh. The cooled reaction solution was washed well with aqueous Na2COs, brine, dried over MgSO4, and concentrated to give the desired product (5.12g, 100percent) as a tan solid:LC/MS (ES) m/z 247.2 [M+H]+

1569-16-0, The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/16610; (2007); A2;,
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.249889-68-7,8-Chloro-2-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (31.83 mg, 163.56 umol, 2.00 eq), 6-[4-(4-methylpiperazin-l-yl)-l-piperidyl]-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrazolo[l,5-a]pyrimidine (74.19 mg, 81.78 umol, 1.00 eq), Pd(dppf)Cl2 (11.97 mg, 16.36 umol, 0.20 eq), K2CO3 (33.91 mg, 245.34 umol, 3.00 eq) in dioxane/H20 (6.00 mL/0.9 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 120C for 1 hour under N2 atmosphere until LCMS showed the starting material was consumed completely. The reaction mixture was concentrated in vacuo to give a residue, which was purified by Biotage flash reversed-phase C-18 column chromatography eluting with MeOH/H20 (MeOH in water from 10% to 100%) to give the product of 2-methoxy-8-[6-[4-(4-methylpiperazin-l- yl)-l-piperidyl]pyrazolo[l,5-a]pyrimidin-3-yl]-l,5-naphthyridine (60) as a yellow solid. LC/MS (method 3): fe = 2.22 min, mlz (M + H)+ = 459.2; NMR (400 MHz, MeOD) delta 9.50 (s, 1H), 8.88 (d, J= 5.2 Hz, 1H), 8.77 (d, J= 2.4 Hz, 1H), 8.67 (d, J = 4.8 Hz, 1H), 8.41 (d, J = 2.8 Hz, 1H), 8.19 (d, J = 9.2 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 4.15 (s, 3H), 3.77-3.74 (m, 2H), 2.82-2.40 (m, 11H), 2.30 (s, 3H), 2.10-2.07 (m, 2H), 1.80-1.69 (m, 2H).

249889-68-7, The synthetic route of 249889-68-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; YU, Paul, B.; HUANG, Wenwei; SANDERSON, Philip, Edward; JIANG, Jian-kang; SHAMIM, Khalida; ZHENG, Wei; HUANG, Xiuli; TAWA, Gregory; LEE, Arthur; ALIMARDANOV, Asaf; HUANG, Junfeng; (357 pag.)WO2018/200855; (2018); A1;,
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.1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

0032-1 1,4-Dioxane (2 mL) and a 2 mol/L sodium carbonate aqueous solution (315 muL) were added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (77 mg), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)dichloropalladium(II) (15 mg) in a nitrogen atmosphere, and the reaction vessel was sealed, followed by stirring at 100 C. for 5 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was collected by separation, washed 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 (hexane-ethyl acetate), thereby obtaining 2-chloro-7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (57 mg) as a white solid. 1H-NMR (CDCl3) delta: 9.15 (1H, d, J=2.0 Hz), 8.35-8.31 (2H, m), 8.04 (1H, s), 8.00 (1H, s), 7.57 (1H, d, J=8.6 Hz), 5.53 (2H, s), 3.68-3.63 (2H, m), 0.99-0.93 (2H, m), 0.00 (9H, s).

1309774-03-5, 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23616-31-1,1,6-Naphthyridin-5(6H)-one,as a common compound, the synthetic route is as follows.

A suspension of XI-3 (2.36 g, 15.7 mmol, 1 eq), N-bromosuccinimide (3.1 g, 17.3 mmol, 1 eq), and 50 mL of 1,2-dichloroethane was stuffed at rt for 3.5 hrs. The mixture was filtered; the solids were washed successively with small amounts of chloroform, water, and diethyl ether, and then dried to leave XI-4 (0.8 g, 23percent yield). MS (ES) m/z (M+H) 226.8.

23616-31-1, As the paragraph descriping shows that 23616-31-1 is playing an increasingly important role.

Reference£º
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
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.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,952059-69-7

Five 20 mL microwave vials were each charged with 4-aminophenol (0.700 mg, 33 mmol) and 3 equivalents of cesium carbonate in 6.0 ml of DMF. The mixture was stirred at RT for 10 minutes. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (1 g, 26 mmol), the reaction vessels were capped and irradiated at 150 C. for 15 min in the microwave, at which time the reaction was determined complete by LCMS. The mixture was allowed to cool to ambient temperature and material from the five vessels was combined. A deep brown solid crashed out with addition of water. Filtered solids, washed with water and dried overnight in the vacuum oven to afford 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as a brown solid. [0359] Alternatively, the title compound may be prepared by the following method: In a nitrogen purged sealed pressure vessel, dissolved 4-aminophenol (0.617 g, 5.65 mmol) in DMF (0.030 L). Cesium carbonate (3.68 g, 11.3 mmol) was added and the mixture was stirred at RT for 5 min. Added 8-chloro-3-methoxy-1,5-naphthyridine (1.00 g, 5.14 mmol), heated to 90 C., stirred for 17 h. The mixture was allowed to cool to RT and was concentrated. The crude material was triturated with methanol, filtered, washed with methanol followed by water, and air dried to yield 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as brown solid. MS [M+H]=268.1; Calc’d 267.3 for C15H13N3O2.

The synthetic route of 952059-69-7 has been constantly updated, and we look forward to future research findings.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.249889-68-7,8-Chloro-2-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,249889-68-7

Example 81 : (S)-3-(2,3-dihydro-benzo [ 1 ,4] dioxin-6-yl)-5- { [2-(6-methoxy- [l,5]naphthyridin-4-ylamino)-ethylamino]-methyl}-oxazolidin-2-one:; 81. i. N1 -(6-methoxy-fl, 5]naphthyridin-4-yl)-ethane-l,2-diamine:; A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (1.71 g, 8.81 mmol) and ethylenediamine (1.18 mL, 2 eq.) was heated slowly to 800C over 1 h and subsequently up to 1000C for 2 h. After cooling to rt, the yellow solution was taken in DCM and successively washed with NaHCO3. The aq. layer was back extracted with DCM (3 times) and the combined org. layers were concentrated to afford the title intermediate as a pale yellow oil (0.98 g, 51% yield). MS (ESI, m/z): 219.4 [M+H+].

249889-68-7 8-Chloro-2-methoxy-1,5-naphthyridine 22244395, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/126024; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem