Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.959558-28-2,4-Bromo-2,7-naphthyridin-1-amine,as a common compound, the synthetic route is as follows.,959558-28-2

A solution of Bromo compound 6a (100 mg, 0.45 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 2b (150 mg, 0.37 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 55 C and allowed to stir 12 h. The reaction was diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL), saturated NH4Cl (1 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 16 was obtained by flash column chromatography. Yield = 35%; TLC Rf = 0.1 (10 % MeOH/CH2Cl2) 1H NMR (500 MHz, DMSO-d6) delta 10.77 (s, 1H), 9.60 (s, 1H), 9.05 (d, J = 2.2 Hz, 1H), 9.00 (d, J = 2.0 Hz, 1H), 8.73 (d, J = 5.7 Hz, 1H), 8.54 (t, J = 2.1 Hz, 1H), 8.38 (s, 1H), 8.20 (s, 1H), 8.04 (d, J = 9.9 Hz, 1H), 7.96 (d, J = 5.7 Hz, 1H), 7.93 (s, 2H), 7.73 (s, 1H), 3.57 (s, 2H), 2.39 (s, 8H), 2.17 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.06, 158.62, 154.11, 152.24, 149.60, 148.90, 148.03, 140.47, 138.31, 137.37, 132.96, 131.83, 130.34, 128.86, 124.01, 120.21, 117.56, 112.05, 100.80, 90.37, 89.95, 57.87, 55.11, 53.02, 46.03; HRMS (ESI+): calcd. for C29H27F3N7O (MH+) 546.2224, found 546.2221

959558-28-2 4-Bromo-2,7-naphthyridin-1-amine 23727075, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

72754-05-3, 6-Bromo-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,72754-05-3

Boronic acid 7: To a solution of compound 6 (10 g, 44.44 mmol) in dry tetrahydrofuran (350 mL) was added sodium hydride (2 g, 66.66 mmol, 80% dispersion) at 0 C. After the mixture was stirred at room temperature for 30 min, the mixture was cooled below -60 C. in a dry ice/acetone bath, and n-butyllithium (70 mL, 112 mmol, 1.6 M in hexane) was added over 30 min. The mixture was kept stirring for another 30 min, then triisopropyl borate (40 mL, 177 mmol) was added dropwise. The reaction mixture was stirred for 10 min, and then warmed to 0 C. slowly in an ice bath. HCl (5 N) was added to the mixture to adjust pH=3-4, and the mixture was stirred for 20 min. Aq. NaOH was added to the mixture to adjust pH=10. After filtration, the organic layer was separated. The aqueous layer was extracted with a mixture of ethyl acetate/THF (4/1; 2¡Á120 mL) and EtOAc (100 mL). The aqueous layer was adjusted to pH=5-6 with HCl. The precipitate thus formed was collected by filtration and dried to give boronic acid 7 (3.5 g, 41%) as a white solid

The synthetic route of 72754-05-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 8-Chloro-3-methoxy-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,952059-69-7

To a microwave vial (10-20 mL) was added (6- (3-methylisoxazol-5-yl) – [1, 2, 4] triazolo [4, 3-b] pyridazin-3 -yl) methanamine (1.00 g, 4.34 mmol) and 8-chloro-3-methoxy-l, 5-naphthyridine (1.10 g, 5.65 mmol) in 2-butanol (12 mL) . The suspension was stirred at 1200C under microwave irradiation for four hours . The mixture was concentrated and taken up in ammonia in methanol (2.0 M) then purified by MPLC chromatography (eluted with 0-10% methanol in dichloromethane) to yield the product as a tan solid. MS m/z = 389.0 [M+l] + . CaIc ‘d for Ci9Hi6N8O2: 388.1

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

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

959558-28-2, 4-Bromo-2,7-naphthyridin-1-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,959558-28-2

A solution of Bromo compound 6a (96 mg, 0.43 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL, 10.8 mmol, 30 equiv) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 3b (150 mg, 0.36 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 50 C and allowed to stir 12 h. The reaction was quenched by addition of NH4Cl (5 mL) at room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 15 was obtained by flash column chromatography. Yield = 49%.; TLC Rf = 0.1 (10 % MeOH/CH2Cl2). 1H NMR (500 MHz, DMSO-d6) delta 10.65 (s, 1H), 9.60 (s, 1H), 8.93 (s, 1H), 8.74 (d, J = 5.7 Hz, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.92 (s, 2H), 7.88 (d, J = 5.7 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 3.55 (s, 2H), 2.80 (s, 3H), 2.37 (s, 8H), 2.14 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.01, 162.28, 158.58, 152.20, 149.63, 148.92, 147.44, 140.37, 138.34, 137.81, 132.86, 131.74, 127.93, 127.77, 123.97, 118.86, 117.71, 117.37, 112.05, 101.07, 92.66, 90.47, 57.90, 55.19, 53.17, 46.19, 24.28; HRMS (ESI+): calcd. for C30H29F3N7O (MH+) 560.2380, found 560.2380

As the paragraph descriping shows that 959558-28-2 is playing an increasingly important role.

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15944-34-0, 7-Chloro-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,15944-34-0

EXAMPLE 1; 7-Oxo-5 ,6,7,8-tetrahydro-ri,81naphthyridine-2-carboxylic acid methyl ester; 7-Chloro-lH-[l,8]naphthyridin-2-one (2 g, 11 mmol) was combined with triethylamine (1.1 g, 11 mmol) and bis (dppf) Pd (II) dichloride-dichloromethane complex (0.84 g, 1.0 mmol) in a 100 cc ss-reactor, purged with nitrogen and then with carbonmonoxide, pressurized to 500 psi, stirred and heated to 100 0C for 15 h. The solution was purged with nitrogen and concentrated then triturated in ethanol. The product was isolated as a solid, (2.1 g, 10 mmol, 92.9%). MS: APCI: M+l: 205.1 (Exact Mass: 204.2). 7-Oxo-5,6,7, 8-tetrahydro-[l,81naphthyridine-2-carboxylic acid7-Oxo-5,6,7,8-tetrahydro-[l,8]naphthyridine-2-carboxylic acid methyl ester (9.71 g, 47.1 mmol) and LiOH (3.9 g, 164 mmol) were stirred overnight in THF at room temperature. TLC showed disappearance of starting material so the reaction was concentrated and the residue was poured over ice water and neutralized withHCl then NH4OH. The solid that formed was collected via vacuum filtration and dried in vacuo then concentrated in toulene to remove water. The product was isolated as a white solid (8.56 g, 44.54 mmol, 94.5%). MS: APCI: M+l: 193.0 (Exact Mass: 192.17).

The synthetic route of 15944-34-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90273; (2006); 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.72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

72754-05-3, 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one To a solution of 6-bromo-1,8-naphthyridin-2(1H)-one (0.1 g, 0.444 mmol) in DMF (2 mL) was added sodium hydride (0.021 g, 0.889 mmol) at 0 C. The reaction was stirred at 0 C. for 30 min, then SEM-Cl (0.118 mL, 0.667 mmol) was added. The reaction was stirred at room temperature overnight, then diluted with ammonium chloride solution, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether to give 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one (0.12 g, 76%). 1HNMR 400 MHz (CDCl3): 0.034 (s, 9H), 0.95-0.99 (m, 2H), 3.73-3.77 (m, 2H), 5.92 (s, 2H), 6.75-6.77 (m, 1H), 7.56-7.58 (m, 1H), 7.96-7.98 (m, 1H), 8.63-8.64 (m, 1H).

As the paragraph descriping shows that 72754-05-3 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); 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.15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.

Preparation B 7-methoxy-1H-[1,8]naphthyridin-2-one To a solution of 7-chloro-1H-[1,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 mL) was added NaOMe (25 wt % in MeOH, 161 mL). The resulting solution was stirred at reflux for 15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added. The phases were separated and the aq. layer was extracted with EA (8*80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid (5.22 g, 100% yield). 1H NMR (d6DMSO) delta: 11.96 (s, 1H); 7.96 (d, J=8.5 Hz, 1H); 7.81 (d, J=9.4 Hz, 1H); 6.63 (d, J=8.5 Hz, 1H); 6.34 (d, J=9.4 Hz, 1H); 3.90 (s, 3H).

15944-34-0, The synthetic route of 15944-34-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); 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.215523-34-5,1,8-Naphthyridine-2-carboxylic acid,as a common compound, the synthetic route is as follows.,215523-34-5

General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM.

215523-34-5 1,8-Naphthyridine-2-carboxylic acid 735156, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Article; Talbot, Amelie; Maltais, Rene; Kenmogne, Lucie Carolle; Roy, Jenny; Poirier, Donald; Steroids; vol. 107; (2016); p. 55 – 64;,
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.17965-71-8,3-Bromo-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,17965-71-8

Nitrogen was flushed into a stirred solution of 3-bromo-1,5-naphthyridine (2 g, 9.56 mmol) in dry toluene for 15min. 1-Ethoxy vinyl tributyltin (3.8 g, 10.52 mmol) and Bis(triphenylphosphine)palladium chloride (0.33 g, 4.7 mmol) were added and the mixture was stirred overnight at 90 C. The reaction mixture was cooled to rt and filtered through celite. The filtrate was concentrated under vacuum. 6N HCI (50 mL) was added to the resulting mixture and the solution was stirred for 1 h at rt. It was then neutralized with a saturated solution of NaHCO3. It extracted with EtOAc (3 x 150 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to get crude product. The crude was purified by flash column chromatography to afford the title compound. Yield: 62% (1.0 g, yellow solid). 1H NMR (400 MHz, DMSO-de): delta 9.39 (d, J = 2.8 Hz, 1 H), 9.14-9.12 (m, 1 H), 8.96 (d, J = 2.4 Hz, 1 H), 8.51 (d, J = 11.6 Hz, 1 H), 7.93-7.89 (m, 1 H), 7.65-7.54 (m, 1 H), 2.50 (d, J = 2.4 Hz, 3H). LCMS: (Method A) 173.2 (M +H), Rt. 1.63 min, 90.89% (Max).

The synthetic route of 17965-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1260670-05-0, 3-Bromo-8-chloro-1,7-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1260670-05-0

Step 2 To a stirred solution of intermediate M-2 (90.0 mg, 0.20 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (74.0 mg, 0.30 mmol) in THF (3 mL) was added LHMDS (1 M in THF, 0.510 mL, 0.51 mmol) at RT and the mixture was heated at 45 C. After 2 h, additional 1 eq. of LHMDS was added and the mixture was stirred overnight at 45 C. The reaction was quenched with saturated NH4C1 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was treated with 5 mL of DCM and TFA (0.5 mL) was added. The mixture was stirred at 25 C for 2 h, then nuetralized with saturated NaHC03 and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by p-TLC (DCM: MeOH = 15 : 1) to afford compound M-3. MS for M-3: m/e = 551 and 553 (M+l).

As the paragraph descriping shows that 1260670-05-0 is playing an increasingly important role.

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