Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55716-28-4,8-Methoxy-1,7-naphthyridin-6-amine,as a common compound, the synthetic route is as follows.,55716-28-4

EXAMPLE 76; N-(2-Chloro-5-(8-methoxy-l,7-naphthyridin-6-yl)pyridin-3-yl)-4- fluorobenzenesulfonamide; (1) 8-methoxy-l,7-naphthyridin-6-yl trifluoromethanesulfonate.; (Some starting materials may be obtained from Parkway Scientific, NY, NY) To a 50 mL round- bottomed flask was added 8-methoxy-l,7-naphthyridin-6-amine (175 mg, 999 mumol), DMF (1.6 mL), trifluoromethane sulfonic acid (0.8 mL, 9041 mumol), sodium nitrite (0.06 mL, 1998 mumol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 40 mL). The organic extract was washed with water (10 mL), satd NaCl (10 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give 8-methoxy-l,7-naphthyridin-6-yl trifluoromethanesulfonate (126mg, 41% yield). MS (ESI pos. ion) m/z calc’d for Ci0H7F3N2O4S: 308.0; found 309.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 4.25 (s, 3 H) 7.13 (s, 1 H) 7.70 (dd, J=8.33, 4.24 Hz, 1 H) 8.19 (dd, J=8.40, 1.53 Hz, 1 H) 9.04 (dd, J=4.24, 1.61 Hz, 1 H)

As the paragraph descriping shows that 55716-28-4 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2009/155121; (2009); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

To a solution of (R)-tert-butyl 3-(1,1-difluoro-4-iodobutyl)pyrrolidine-1-carboxylate (700 mg, 1.88 mmol) and 2-methyl-1,8-naphthyridine (407 mg, 2.82 mmol) in THF (12 mL) at 0¡ã C. was added LiHMDS (2.82 mL, 1M, 2.82 mmol). The reaction mixture was stirred at 0¡ã C. for 3 h, then quenched with saturated ammonium chloride solution (6 mL), diluted with water (15 mL) and extracted with EtOAc (30 mL¡Á2). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-TLC to give the desired product tert-butyl 3-(5-(1,8-naphthyridin-2-yl)pentyl)-3-fluoropyrrolidine-1-carboxylate as a light yellow solid (350 mg). Yield 48percent (ESI 388 (M+H)+).

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

Reference£º
Patent; Lazuli, Inc.; Harrison, Bryce A.; Bursavich, Matthew G.; Brewer, Mark; Gerasyuto, Aleksey I.; Hahn, Kristopher N.; Konze, Kyle D.; Lin, Fu-Yang; Lippa, Blaise S.; Lugovskoy, Alexey A.; Rogers, Bruce N.; Svensson, Mats A.; Troast, Dawn M.; (172 pag.)US2018/244648; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

254-60-4, 1,8-Diazanaphthalene is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,254-60-4

Example 125: 4-Chloro-N-[5-chloro-2-(3,4-dihvdro-2H-H ,81naphthyridine-1 – carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide; [00531] 5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (208 mg, 0.50 mmol), 1 ,2,3,4-tetrahydro-[1 ,8]naphthyridine [(135 mg, 1.0 mmol) 1 ,2,3,4-tetrahydro-[1,8]naphthyridine was prepared freshly from 1,8- napthyridine via hydrogenation over Pt2O], BOP (486 mg, 1.1 mmol), DIEA (185 mg, 1.4 mmol) were reacted according to the procedure for the synthesis of 5- chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)-picolinic amides. HPLC purification (20 ? 90% gradient of MeCN-water) provided 4-chloro-N-[5-chloro- 2-(3,4-dihydro-2H-[1 ,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl- benzenesulfonamide: MS m/z. 531.0 (M+H).

254-60-4 1,8-Diazanaphthalene 136069, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

A common heterocyclic compound, the naphthyridine compound, name is 2,7-Naphthyridin-1-amine,cas is 27225-00-9, mainly used in chemical industry, its synthesis route is as follows.

4-Bromo-2,7-naphthyridin-1-ylamine32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25% aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

27225-00-9, As the rapid development of chemical substances, we look forward to future research findings about 27225-00-9

Reference£º
Patent; Merck Patent GmbH; Jonczyk, Alfred; Zenke, Frank T.; Amendt, Christiane; US2015/252041; (2015); A1;,
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,10261-82-2

To a suspension of Intermediate 3 (5.9 g) in dry DME (180 ml) and dry DMF (45 ml) at 0C under argon was added in portions NaH (60% w:w dispersion in mineral oil, 3.2 g). After stirring for 45 minutes, the mixture was treated with lithium bromide (8.8 g) and the suspension was allowed to warm to room temperature. After stirring for 45 minutes, the mixture was treated with allyl bromide (7 ml) and then stirred at 65C for 3 h. The mixture was cooled to room temperature and concentrated under reduced pressure, then t-BuOMe (300 ml) was added and the mixture was then washed with 1 N NH4Cl (200 ml). The combined aqueous phases were extracted with t-BuOMe (2 x 100 ml). The organic phases were combined, washed with brine (200 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (4.29 g, 57%). To obtain an additional amount of the desired compound, the combined aqueous phases were extracted exhaustively with CH2Cl2. Then, the organic extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (1.5 g, 20%). [ES MS] m/z 187 (MH+).

As the paragraph descriping shows that 10261-82-2 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; EP2080761; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

A common heterocyclic compound, the naphthyridine compound, name is 7-Chloro-1,8-naphthyridin-2-ol,cas is 15944-34-0, mainly used in chemical industry, its synthesis route is as follows.

To a solution of 7-chloro-l,8-naphthyridin-2(lH)-one (2.7 g, 15.2 mmol) (J.Org.Chem. 1990, 55, 4744-4750) in N,N-dimethylformamide (4OmL) under nitrogen at O0C was added sodium hydride (0.73 g, 18.3 mmol). The slurry was stirred for ten minutes and then (2- bromoethoxy)-t-butyl dimethylsilane (4.3 g, 18.3 mmol) was added. The mixture was heated at 8O0C for two hours then cooled to room temperature. The reaction mixture was quenched with water and the product extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with 20% acetone in n-hexane gave the product as an oil (3.2 g, 62%).MS CES): 338 (MH+) for C16H23N2SiClO21H NMR fDMSO-d): delta ppm -0.00 (s, 6H); 0.81 (s, 9H); 3.91 (t, 2H); 4.53 (t, 2H); 6.80 (d,IH); 7.45 (d, 1 H); 8.06 (d, IH); 8.29 (d, IH).

15944-34-0, As the rapid development of chemical substances, we look forward to future research findings about 15944-34-0

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71964; (2008); 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

7689-62-5, A solution of the compound 0001-2 (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) was stirred at 85C for 5 minutes. A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was dropwise added thereto. Further acetic acid (2 mL) was added dropwise thereto, and the mixture was stirred at 85C for 3 hours. To a 6 M aqueous sodium hydroxide solution (60 mL) under stirring with ice-cooling, the reaction solution which had been cooled to room temperature was added dropwise. The precipitated solid was separated by filtration, and the solid was then suspended in methanol (5 mL), and thereafter subjected to sonication. Thereafter, the suspension was filtered, and then the resulting solid was washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v% aqueous methanol solution (8 mL), subjected to sonication, and then the suspension was filtered, and the residue was then washed with a 75 v/v% aqueous methanol solution twice to obtain a compound 0001-3 (3.33 g) as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.13 (1H, d), 8.77 (1H, dd), 8.53 (1H, dd), 7.91 (1H, d). MS m/z (M+H): 245.

7689-62-5 2-Chloro-1,5-naphthyridine 15153031, anaphthyridine compound, is more and more widely used in various.

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

A common heterocyclic compound, the naphthyridine compound, name is 3-Bromo-1,5-naphthyridine,cas is 17965-71-8, mainly used in chemical industry, its synthesis route is as follows.

A solution of ethyl 2,3-dihydro-lH-isoindole-4-carboxylate hydrochloride (80 mg, 0.35 mmol), 3-bromo-l,5-naphthyridine (144 mg, 0.69 mmol), Pd2(dba)3-chloroform adduct (18.2 mg, 0.018 mmol), XantPhos (20.3 mg, 0.04 mmol), and cesium carbonate (344 mg, 1.06 mmol) in toluene (5 mL) stirred for 16 h at 100 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 2×20 mL of dichloromethane, and the combined organic phases were washed with 1×10 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 20:1 dichloromethane/methanol) to afford ethyl 2-(l,5-naphthyridin-3-yl)-2,3-dihydro-lH-isoindole-4-carboxylate (110 mg, 98%) as a red solid. MS: (ESI, m/z): 320[M+H]+.

17965-71-8, As the rapid development of chemical substances, we look forward to future research findings about 17965-71-8

Reference£º
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

A common heterocyclic compound, the naphthyridine compound, name is 7-Bromo-2-chloro-1,5-naphthyridine,cas is 1309774-03-5, mainly used in chemical industry, its synthesis route is as follows.

0039-1 A solution of 7-bromo-2-chloro-1,5-naphthyridine (2.04 g), 5-cyclopentyl-1,3,4-thiadiazole-2-amine (1.41 g), and potassium carbonate (1.73 g) in dimethylsulfoxide (16 mL) was stirred at 130 C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, and the solid matter was collected by filtration, thereby obtaining N-(7-bromo-1,5-naphthyridin-2-yl)-5-cyclopentyl-1,3,4-thiadiazole-2-amine (1.92 g). 1H-NMR (DMSO-d6) delta: 12.20 (1H, s), 8.84 (1H, d, J=2.7 Hz), 8.56 (1H, d, J=2.7 Hz), 8.31 (1H, d, J=9.3 Hz), 7.51 (1H, d, J=9.3 Hz), 3.56-3.40 (1H, m), 2.22-2.08 (2H, m), 1.94-1.34 (6H, m). MS m/z (M+H): 376, 378.

1309774-03-5, As the rapid development of chemical substances, we look forward to future research findings about 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

Step 1 To a mixture of 3-bromo-8-chloro-l ,7-naphthyridine J-1 (4.00 g, 16.4 mmol), but-2-yn-l-ol (1.78 g, 24.6 mmol), Cs2C03 (8.03 g, 24.6 mmol), and 5-(di-ieri-butylphosphino)-l’,3′,5′- triphenyl-rH-l ,4′-bipyrazole (1.67 g, 3.29 mmol) in THF (40 mL) was added diacetoxypalladium (0.574 g, 1.64 mmol) under N2. The mixture was stirred at 70 C for 4 h and concentrated; the residue was purified directly by silica column chromatography (PE: EtOAc = 3: 1) to afford compound J-2. MS for J-2: m/e = 233 (M+l).

1260670-05-0, 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