Month: November 2020

As a common heterocyclic compound, it belong naphthyridine compound,7-Chloro-1,8-naphthyridin-2-ol,15944-34-0,Molecular formula: C8H5ClN2O,mainly used in chemical industry, its synthesis route is as follows.,15944-34-0

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).

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Chloro-1,8-naphthyridin-2-ol,belong naphthyridine compound

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

3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0, it is a common heterocyclic compound, the naphthyridine compound, 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

1260670-05-0 is used more and more widely, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine

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-Chloro-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 7689-62-5, its synthesis route is as follows.,7689-62-5

2-chloro- 1 ,5-naphthyridine ( 10- 1 ) (35 g, 213 mmol) in toluene (420 mL) was treated with tributyl(vinyl)stannane (101 g, 93.4 mL, 319 mmol) and tetrakis( phenylphosphine)palladium (36.9 g, 31.9 mmol). The mixture was heated at 140 C under microwave irradiation for 20 min, then cooled and concentrated in vacuo. The residue was purified by silica gel flash column chromatography, eluting with 0-100% EtO Ac/heptane. The fractions containing the desired product (10-2) were pooled, and after solvent removal in vacuo, 19 g (57%) of the product were obtained. LC/MS: m/z (M+H) = 157.2.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Chloro-1,5-naphthyridine

Reference£º
Patent; MERCK SHARP & DOHME CORP.; BARROW, James, C.; COX, Christopher, D.; NOLT, Mark, B.; SHIPE, William, D.; WO2013/74390; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Chloro-1,8-naphthyridin-2-ol, and cas is 15944-34-0, its synthesis route is as follows.,15944-34-0

A suspension of 300 mg (1.66 mmole) OF7-CHLORO-LH- [1, 8] naphthyridin-2-one (J. ORG. Chem. 1990, 55, 4744-4750) in 5 ML of anhydrous DMF was cooled to 0 C in an ice bath under a N2 atmosphere. A solution of 1.0 M lithium bis (trimethylsilyl) amide in THF (2.0 mL, 2.0 mmole) was added in a dropwise fashion. After stirring at 0 C for 5 min. , 381 mg (2.49 mmole) of 1-bromo-3-methoxypropane was added. The ice bath was removed, and the reaction mixture was stirred at room temperature for 5 min. An additional 5 ML of anhydrous DMF was added, and the heterogeneous mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with EtOAc, and washed with H20 (3x) and brine. The organic layer was dried over MGS04, filtered, and concentrated. Purification by flash column chromatography (SIO2, 40% EtOAc/hexanes gradient to 60% EtOAc/hexanes) gave 304 mg (72 %) of 7-chloro- 1-(3-methoxypropyl)-1H-[1,8]naphthyridin-2-one. MS : NEZ 253. 1,255. 1 (M+I)

With the complex challenges of chemical substances, we look forward to future research findings about 15944-34-0,belong naphthyridine compound

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

A solution of 2-Methyl-l ,8-naphthyridine (0.037 g, 0.257 mmol), Intermediate 25 (0.100 g, 0.257 mmol) and 4-methylbenzenesulfonamide (0.044 g, 0.257 mmol) in toluene (0.555 mL) was stirred at 110 C for 14 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was purified by preparative HPLC (Phenomenex Luna AXIA 5u21.2xl00 mm, 10 min gradient, 15 min run, 10% to 100% Solvent B = 90% MeOH-10% H2O-0.1%TFA, Solvent A = 10% MeOH-90% H2O-0.1%TFA) to afford TFA salts of IB and IE, respectively. These salts were individually dissolved in MeOH (1.000 mL) and 250 mg Dianion WA21J resin was added. After stirring at room temperarture for 1 h, the resin was removed by filtration and washed well with MeOH. The filtrates were concentrated in vacuo to afford IB (25.8 mg, 20%) as an orange-brown oil and IE (32.5 mg, 19%) as a brown oil, respectively. IB: NMR (500MHz, CDCb) 59.06 (dd,J=4.1, 1.9 Hz, 1H), 8.16-8.05 (m, 2H), (0395) 7.92 (d,J= 16.0 Hz, 1H), 7.54 (d,J= 8.3 Hz, 1H), 7.39 (dd,J= 8.0, 4.1 Hz, 1H), 7.25 (d, J= 1.4 Hz, 1H), 7.13-7.04 (m, 3H), 6.98 – 6.86 (m, 2H), 6.32 (dd,J=8.8, 7.2 Hz, 1H), 4.17 – 4.05 (m, 3H), 4.02 – 3.95 (m, 1H), 3.88 (s, 3H), 3.64 – 3.55 (m, 1H), 3.34 – 3.25 (m, 1H), 3.05 – 2.92 (m, 2H), 1.20 (t, J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 515.1 [M+H]+ (0396) IE.: NMR (500MHz, CDCB) delta 9.04 (dd,J=4.1, 1.9 Hz, 1H), 8.07 (dt,J=8.0, 1.5 Hz, 2H), 7.95 (d, J= 8.3 Hz, 2H), 7.48 – 7.31 (m, 4H), 7.08 – 7.00 (m, 2H), 6.93 – 6.83 (m, 1H), 6.81 (d,J=1.7Hz, 1H), 6.52 (d,J=1.7Hz, 1H), 6.23 (dd,J=8.7, 7.3 Hz, 1H), 4.26 (t, J= 7.4 Hz, 1H), 4.07 (q, J= 7.1 Hz, 2H), 3.92 – 3.79 (m, 4H), 3.77 – 3.68 (m, 1H), 3.48 – 3.33 (m, 5H), 3.20 – 3.08 (m, 1H), 3.02 – 2.81 (m, 3H), 1.12 (t,J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 659.2 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 1569-16-0,belong naphthyridine compound

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (95 pag.)WO2019/94319; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

2-methyl-1,8-naphthyridine (288 mg, 2 mmol) and twice the equimolar amount of selenium dioxide (221.92 mg-443.84 mg, 2 mmol-4 mmol) was dissolved in 50 ml of 1,4-dioxane under nitrogen or without nitrogen protection at 80 ¡ã C to 130 ¡ã C for 8-16 hours. During the reaction, the silica gel plate was detected at any time until the basic reaction of 2-methyl-1,8-naphthyridine was completed and a new point was generated. After completion of the reaction, the reaction mixture was suspended, purified on silica gel column with dichloromethane to obtain 1,8-naphthyridine-2-aldehyde., 1569-16-0

With the rapid development of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY, CHINESE ACADEMY OF SCIENCES; FU, WENFU; ZHAO, CHUNCHAO; (14 pag.)CN104974181; (2017); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 2-Methyl[1,8]-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

In a 25 mL microwave reaction tube,Adding 2-methylnaphthyridine,Salicylaldehyde 0.5 g (4 mmol) and 10 ml acetic anhydride,Forming an orange-red solution,At a controlled temperature of 130 ¡ã C,Microwave power 50W, microwave reaction 40min,With the thin layer of the reaction process to monitor;After the reaction,The solvent was concentrated under reduced pressure to remove acetic anhydride,Oil-like viscous liquid,Dissolved with hot ethanol,Then recrystallized from acetone,Precipitation of yellow powder,That is, 2- (2′-hydroxystyryl) naphthyridine probe reagent,Yield 35percent.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; Guizhou University; Ceng, Xi; Ruan, Qin; Mou, Lan; Li, Zhao; Zhang, Hong; (29 pag.)CN106045996; (2016); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-8-chloro-1,7-naphthyridine, and cas is 1260670-05-0, its synthesis route is as follows.,1260670-05-0

Ammonium hydroxide (40 mL, 1.04 mol, 28%) was added to a solution of 3-bromo- 8-chloro-l,7-naphthyridine (1.00 g, 4.11 mmol) and THF (10 mL) in a sealed tube. The mixture was sealed, stirred at 100 C overnight, diluted with H20 (100 mL), and then extracted with EtOAc (3 x50 mL). The combined organic layers were washed (2x 100 mL brine), dried (Na2S04), filtered, and concentrated to dryness to give Intermediate 9 (824 mg, 89%) as a yellow solid. 1H NMR (400MHz, DMSO-i): delta 8.81 (s, 1H), 8.51 (s, 1H), 7.90 (d, 1H), 7.05 (br s, 2H), 6.87 (d, 1H); MS: 223.9 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 1260670-05-0,belong naphthyridine compound

Reference£º
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (167 pag.)WO2018/170167; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

2-chloro-1,8-naphthyridine (89 mg, 0.54 mmol), 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (100 mg, 0.431 mmol), and cesium carbonate (202 mg, 0.620 mmol) were suspended in dry dimethylformamide (0.86 mL) under nitrogen and heated to 100 C. for 18 h. The mixture was cooled and extracted with ethyl acetate and water. The phases were separated and the organic was dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using the ISCO (0-100% EtOAc in hexane), gave the desired 5-(trans-3-((1,8-naphthyridin-2-yl)amino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (32 mg, 0.089 mmol, 21% yield) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) delta: ppm 1.45 (s, 6H) 2.42 (ddd, J=13.88, 9.28, 3.29 Hz, 2H) 3.44-3.62 (m, 2H) 5.22-5.38 (m, 2H) 6.71 (d, J=8.92 Hz, 1H) 7.16 (dd, J=7.82, 4.46 Hz, 1H) 7.79-7.98 (m, 2H) 8.11 (q, J=3.12 Hz, 2H) 8.84 (dd, J=4.38, 1.90 Hz, 1H)., 15936-10-4

15936-10-4 is used more and more widely, we look forward to future research findings about 2-Chloro-1,8-naphthyridine

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

72754-05-3, 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. 6-Bromo-1,8-naphthyridin-2-ol, cas is 72754-05-3,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Step 1: To a stirred solution of 6-bromo-1,8-naphthyridin-2(1H)-one (1 equiv) in DIVIF (0.2 M) at 25 C were added cesium carbonate (1.3 equiv) and iodoethane (1.1 equiv) and the reaction was stirred for 30 mm. The mixture was poured onto water and extracted three times with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated to give 6-bromo-1-ethyl-1,8-naphthyridin-2(1H)-one as a yellow solid in 87% yield, which was used without further purification. LCMS (m/z) (M+H) = 253.0/255.0, Rt = 0.91 mm

The chemical industry reduces the impact on the environment during synthesis,72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,I believe this compound will play a more active role in future production and life.

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