Month: August 2020

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Int-19B. Ethyl (?)-4-(2-(l,8-naphthyridin-2-yl)vinyl)-lH-pyrrole-2-carboxylate: A solution of Int-19A (0.300 g, 2.08 mmol), commercially available ethyl 4-formyl-lH- pyrrole-2-carboxylate (0.348 g, 2.08 mmol), and 4-methylbenzenesulfonamide (0.356 g, 2.08 mmol) in toluene (4.5 mL) was stirred at reflux for 21 h. The precipitate was collected, triturated with DCM (2x) and the solid air-dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid. NMR (500 MHz, DMSO-c) delta 12.14 (br. s., 1H), (0504) 9.01 (dd, J = 4.3, 2.1 Hz, 1H), 8.41 – 8.28 (m, 2H), 7.82 (d, J = 16.2 Hz, 1H), 7.76 (d, J = 8.5 Hz, 1H), 7.52 (dd, J = 8.0, 4.1 Hz, 1H), 7.46 (s, 1H), 7.24 – 7.16 (m, 2H), 4.27 (q, J = (0505) 7.2 Hz, 2H), 1.31 (t, J= 7.0 Hz, 3H). HPLC retention time (Method 1): 1.973 mia; LCMS (ES): m/z 294.0 [M+H]+.

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (117 pag.)WO2018/89360; (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.

0003-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (30 mg), 1,3,4-thiadiazole-2-amine (25 mg) and potassium carbonate (17 mg) in dimethylsulfoxide (0.5 mL) was stirred at 150 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and water was added thereto. The solid matter was collected by filtration, thereby obtaining N-(7-bromo-1,5-naphthyridin-2-yl)-1,3,4-thiadiazole-2-amine.

The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

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

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-methyl-l,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35mL) was added 10percent Pd/C, and the reaction mixture was stirred under H2 (10 psi) for 24 hours.Palladium was filtered out through celite and washed with excess ethanol. The filtrate wasconcentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) 5 7.07 (d, 1H, J= 7.38 Hz), 6.32 (d, 1H, J = 7.25 Hz), 3.36-3.33 (m, 2H), 2.76-2.65 (m, 2H), 2.22 (s, 3H),25 1.87-1.82 (m, 2H). M+H=149.15.

1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; PHARMACIA CORPORATION; WO2005/51904; (2005); 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.15992-83-3,1,8-Naphthyridin-2-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 20 The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (4.55 g), N,N’-carbonyldiimidazole (6.55 g) and 2-amino-1,8-naphthyridine (5.2 g). The product produced by precipitation in water (8.35 g; m.p. 85 C., viscous) is filtered and then dissolved in boiling 1-propanol (50 cc). After 1 hour’s cooling at 4 C., the crystallized solid is separated by filtration, washed with 1-propanol (2*5 cc) and dried at 35 C. under reduced pressure (0.067 kPa). N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide (6.9 g) is produced, m.p. 150 C. 2-Amino-1,8-naphthyridine can be prepared according to U.S. Pat. No. 3,948,917.

The synthetic route of 15992-83-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Rhone-Poulenc Sante; US4642308; (1987); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

To the compound 0001-1 (2.76 g), phosphorous oxychloride (8.3 mL) was added, and the mixture was stirred at 100C for 5 hours. The reaction solution which had been cooled to room temperature was added dropwise to a mixture of ethyl acetate (30 mL), water (30 mL), and sodium carbonate (9.57 g) in an ice-cooling bath over one hour. Further, water (10 mL) was added thereto, and sodium carbonate was added thereto until the pH reached 8.3. After stirring at room temperature for 10 minutes, the resulting mixture was subjected to liquid separation by the addition of ethyl acetate (270 mL) and water (200 mL). Further, the aqueous layer was extracted with ethyl acetate (200 mL) twice. The collected organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to obtain a compound 0001-2 (2.86 g) was obtained as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.05 (1H, dd), 8.50 (1H, dd, J=8.9), 8.41 (1H, ddd), 7.87, (1H, d), 7.86 (1H, m).

The synthetic route of 10261-82-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-methyl-1,8-naphthyridine (6.024 g, 41.8 mmol) (from step 1) in anhydrous THF (140 mL) at -40 ¡ãC under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (88.0 mL) and the reaction mixture was stirred at -40 ¡ãC for 30 min to give a blood-red solution. After stirring for 30 min at – 40 ¡ãC, neat diethyl carbonate (5.60 mL) was added drop wise to above solution in 5 min and the reaction mixture was warmed up to 0 ¡ãC (ice-bath) and stirred at that temperature for 2 h to give a dark reddish-orange solution. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (60.0 mL) to give an orange-red solution and the THF was removed in vacuo to give an orange-red mixture. The resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4/MgSO4, filtered and evaporated in vacuo to afford a dark orange-red crystalline solid (8.65 g). The crude residue was purified by Silica-gel flash chromatography using a Varian SF-40-120 g Super Flash silica gel column and elution with 10-100percent ethyl acetate in n-heptane to afford the desired product as a yellow-orange crystalline solid (7.76 g, yield 85percent). LC-MS analysis of the solid shows the desired product’s mass: m/z 217 (M+H) and m/z 239 (M+Na); Calculated for C12H12N2O2: 216.23. 1H NMR (400 MHz, DMSO-d6): delta 1.21 (t, J = 7.0 Hz, 3H), 4.10 (q, 2H), 4.89 (s, 1H), 6.77 (d, J = 9.38 Hz, 1H), 7.14 (m, 1H), 7.46 (d, J = 9.36 Hz, 1H), 7.89 (d, 1H), 8.36 (d, 1H), 11.80 (brs, 1H, -OH). 1H NMR of the isolated product was superimposable with that of an authentic sample of the product.

1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (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.1375301-90-8,3-Bromo-1,7-naphthyridin-8(7H)-one,as a common compound, the synthetic route is as follows.

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

The synthetic route of 1375301-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7689-62-5, 2-Chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A glass microwave reaction vessel was charged with 1-(trans-4-aminocyclohexyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.1050 g, 0.339 mmol), 2-chloro-1,5-naphthyridine (0.067 g, 0.407 mmol, 00358), and diisopropylethylamine (0.177 ml, 1.017 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (0.484 ml) and heated to 120 C. for 2 days. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, 100*50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 15 min. Fractions containing product were collected and concentrated. The product was taken up in DCM and loaded onto a Silicycle Si-carbonate cartridge and washed with DCM and MeOH to remove any salts to give the title compound (6.4 mg, 0.016 mmol, 4.7% yield). LCMS showed product peak at 1.434 min (m+1=402.0). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.09-1.24 (m, 4H) 1.37-1.53 (m, 2H) 1.94 (d, J=11.93 Hz, 2H) 2.39 (d, J=12.13 Hz, 2H) 2.68 (qd, J=12.91, 3.13 Hz, 2H) 2.97-3.09 (m, 1H) 4.08-4.24 (m, 1H) 4.47 (tt, J=12.32, 3.91 Hz, 1H) 6.85 (d, J=9.19 Hz, 1H) 7.45 (dd, J=8.41, 4.30 Hz, 1H) 7.91-7.96 (m, 2H) 7.97 (d, J=8.61 Hz, 1H) 8.03 (d, J=9.19 Hz, 1H) 8.60 (d, J=3.33 Hz, 1H)

As the paragraph descriping shows that 7689-62-5 is playing an increasingly important role.

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

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

General procedure: (Method C5) Synthesis of N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine A pyrex reaction tube was charged with 8-chloro-3-methoxy-1,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol (80 mg, 0.26 mmol), cesium carbonate (249 mg, 0.76 mmol) and DMSO (2 mL). The tube was sealed and the reaction mixture was heated to 130 C. After 3.5 h, an aliquot was analyzed by LCMS, and the desired product was determined to be the major peak. The reaction mixture was diluted with DMSO and purified by Gilson HPLC {5-65% (0.1% TFA in CH3CN) in H2O over 20 min}. The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with DCM. The organic portion was dried with Na2SO4, filtered, and concentrated to afford material that was further purified by silica gel chromatography, 90/10/1 CH2Cl2/MeOH/NH4OH. This provided N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine as pure material. MS [M+H]=473.01.48 minutes. Calc’d for C28H20N6O2: 472.5.

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

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

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3.1: 7-Bromo-[1,5]naphthyridin-2-ylamine [Show Image] In a sealed reactor, 500 mg (1.23 mmol, 1 eq) of 7-bromo-2-chloro-1,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 8,57 (d, 1H); 8,05 (d, 1H); 7,96 (d, 1H); 6,04 (d, 1H); 6,98 (s, 2H) ppm. MS: m/z 225 (M+H+).

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; Aeterna Zentaris GmbH; EP2332939; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem