Heterocyclic Building Blocks-Naphthyridine

As a common heterocyclic compound, it belong naphthyridine compound,3-Bromo-8-chloro-1,7-naphthyridine,1260670-05-0,Molecular formula: C8H4BrClN2,mainly used in chemical industry, its synthesis route is as follows.,1260670-05-0

To a solution of 3-bromo-8-chloro-1,7-naphthyridine (2.43g) in toluene (30 mL), EtOH (10 mL), and 10%Na 2CO 3 aq. (10 mL)pd (dppf) Cl 2. DCM (420 mg) was added. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.1g) was added dropwise under N 2 protection. The mixture was allowed to stir at 100C for 16h. The reaction was quenched by H 2O (50 mL)and extracted by EtOAc for 3 times. Organic layer was combined and washed with brine. The resulting solution was concentrated and purified by silicagel (eluting with hexane-EtOAc using a gradient from 8: 1 to 5: 1) to afford 8-chloro-3-vinyl-1,7-naphthyridine (1.1g)as a brown solid. 88%).

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine,belong naphthyridine compound

Reference£º
Patent; BETTA PHARMACEUTICALS CO., LTD; ZHANG, Yao; WANG, Yiqian; FU, Bang; CHEN, Jie; WANG, Jiabing; DING, Lieming; (43 pag.)WO2020/15716; (2020); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 5,7-Dichloro-1,6-naphthyridine, and cas is 337958-60-8, its synthesis route is as follows.,337958-60-8

To a 40 mL vial was added 5,7-dichloro-1,6-naphthyridine, (510 mg, 2.56 mmol), tert-butyl (1R,3s,5S)-3 -amino-9-azabicyclo [3.3.1 jnonane-9-carboxylate (677 mg, 2.82 mmol), DIPEA (1.34 mL, 7.69 mmol), and DMSO (8.54 mL). The vial was capped and the reaction mixture was heated to 110 C and stirred for 16 h. The reaction mixture was5 diluted with water and brine and extracted with EtOAc (4 x 30 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford the desired product as a brown solid which was dissolved in a minimal amount of DCM and adsorbed onto Celite, purified by column chromatography (40 g column; 0-100% EtOAc in hexanes) to afford the title product as a yellow solid (901.6 mg, 86 % yield; 9910 % purity). (m/z): [M+Hj calcd for C21H27C1N402 403.18, found 403.3.

With the complex challenges of chemical substances, we look forward to future research findings about 5,7-Dichloro-1,6-naphthyridine

Reference£º
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.,952059-69-7

The 2-[3-methoxy-5-(7-methoxy-l,5-naphthyridin-4-yloxy)pyridin-2-yl]acetic acid used s as a starting material was prepared as follows :; -Under an atmosphere of argon, a mixture of 4-chloro-7-methoxy-l,5-naphthyridine (0.3 g), methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate (0.303 g), caesium carbonate (1.51 g) and DMF (3 ml) was stirred and heated to 90C for 5 hours. The resultant mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The 0 organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained methyl 2-[3-methoxy-5-(7-methoxy- l55-naphthyridin-4-yloxy)pyridin-2-yl]acetate as a solid (0.395 g); 1H NMR Spectrum: (CDCl3) 3.76 (s, 3H), 3.84 (s, 3H)5 3.93 (s, 2H), 4.02 (s, 3H), 6.74 (d, IH)5 7.11 (d, IH)5 7.69 s (d, IH)5 8.14 (d, IH)5 8.69 (d, IH)5 8.78 (d, IH); Mass Spectrum: M+H4″ 356.

952059-69-7 is used more and more widely, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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

Step 5 2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridine The compound was prepared according to the procedure as described in WO 0033838. To a solution of 2-methyl-1,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35 ml) 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 was concentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) delta 1.82-1.87 (m, 2H), 2.22 (s, 3H), 2.65-2.76 (m, 2H), 3.33-3.36 (m, 2H), 6.32 (d, 1H, J=7.25 Hz), 7.07 (d, 1H, J=7.38 Hz). Mass spectrometry: 149.15 (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; Khanna, Ish Kumar; Clare, Michael; Gasiecki, Alan F.; Rogers, Thomas; Chen, Barbara; Russell, Mark; Lu, Hwang-Fun; US2002/77321; (2002); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

55716-28-4, 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. 8-Methoxy-1,7-naphthyridin-6-amine, cas is 55716-28-4,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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)

The chemical industry reduces the impact on the environment during synthesis,55716-28-4,8-Methoxy-1,7-naphthyridin-6-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

2-Methyl-1,8-naphthyridine (1.1592 g, 8.0 mmol) and SeO2 (1.2452 g, 11.2 mmol) were added to 20 mL of 1,4-dioxane. The mixture were refluxed for 4 h in nitrogen atmosphere and filtered. The filtrate was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, ethyl acetate) (0.71 g, 56.6percent yield). Characterization of 1,8-naphthyridine-2-aldehyde: HRMS (EI) m/z: calcd for C9H7N2O [M+H]+, 159.0588; found, 159.0561. 1H NMR: (400 MHz; DMSO; TMS) 10.15 (s, 1H), 9.24-9.26 (m, 1H), 8.71 (d, 1H), 8.60-8.62 (m, 1H), 8.08 (d, 1H), 7.78-7.80 (m, 1H). 13C NMR (100 MHz, DMSO): 194.3, 155.8, 155.5, 155.0, 140.5, 138.3, 125.6, 124.9, 118.5.

1569-16-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1569-16-0 ,2-Methyl[1,8]-Naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Article; Liu, Xingjiang; Chen, Mingxing; Liu, Ziping; Yu, Mingming; Wei, Liuhe; Li, Zhanxian; Tetrahedron; vol. 70; 3; (2014); p. 658 – 663;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 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. 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

2-(2-(7-Methoxyquinolin-4-ylamino)ethyl)-6-phenylpyridazin-3(2H)- one. A mixture of 2-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one (60 mg, 743 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (55 mg, 282 mumol) in iPrOH (2 mL) was heated to 150 0C for 15 min under microwave. The mixture was filtered and the filtrate was chromatographed on silica with 2-5% (2N NH3-MeOH) in CH2Cl2 to give the product as a white solid (60 mg). MS (ESI pos. ion) calc’d for C2IHi9N5O2: 373.1; found 374.2 (MH+). 1H NMR (400 MHz, Chloroform-d) delta ppm 3.81 – 3.89 (m, 2 H) 3.92 (d, J=I.37 Hz, 3 H) 4.64 (t, J=5.48 Hz, 2 H) 6.54 (dd, 1 H) 7.03 (dd, J=9.78, 1.57 Hz, 1 H) 7.10 (s, 1 H) 7.39 – 7.48 (m, 4 H) 7.66 (dd, J=9.59, 1.56 Hz, 1 H) 7.70 – 7.79 (m, 2 H) 8.38 (t, 1 H) 8.46 (dd, 1 H).

The chemical industry reduces the impact on the environment during synthesis,952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

254-60-4, 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. 1,8-Diazanaphthalene, cas is 254-60-4,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Step C 2-Chloro-3-cyclopropyl-[1,8]naphthyridine (2-5) A mixture of naphthyridine 2-4 (14 g, 77 mmol) and 100 mL POCl3 and 0.1 mL DMF was refluxed at 120 C. for 3 hr and concentrated. The residue was treated with 300 mL ice-water and solid K2CO3 until pH=9. The mixture was extracted three times with ethyl acetate, washed with brine and dried over MgSO4. After solvent removal, the desired compound 2-5 was obtained as a yellowish solid. 1H NMR (400 MHz, CDCl3): delta9.00 (q, 1H), 8.10 (q, 1H), 7.78 (s, 1H), 7.50 (q, 1H), 2.34 (m, 1H), 1.00 (m, 2H), 0.82 (m, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,8-Diazanaphthalene, 254-60-4

Reference£º
Patent; Wang, Jiabing; US2004/38963; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1260670-05-0, 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. 3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Step 1 To a 100 mL sealed tube was added 3~bromo-8-chloro-l,7-naphthyridine K-l (1.00 g, 4.10 mmol), 1,4-dioxane (15 mL) and NH3_H20 (40 mL) at room temperature. The mixture was sealed and stirred at 100 C for 15 h, then cooled and partitioned between water (150 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (50 mL x 2) and the combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound K-2. MS for K-2: m/e = 224 and 226 (M+l).

The chemical industry reduces the impact on the environment during synthesis,1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,I believe this compound will play a more active role in future production and life.

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

Name is 7-Bromo-2-chloro-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1309774-03-5, its synthesis route is as follows.

Example 0929 N,N-dimethylacetamide (75 mL), 5-isopropylpyridazine-3-amine (5.12 g) and sodium tert-amyl oxide (9.08 g) were added to 7-bromo-2-chloro-1,5-naphthyridine (9.58 g), followed by stirring at 80 C. for 1 hour. The reaction mixture was poured into water (300 mL), and the precipitated solid was collected by filtration and washed with ethanol, thereby obtaining 7-bromo-N-(5-isopropylpyridazin-3-yl)-1,5-naphthyridine-2-amine (7.70 g) as a brown solid. 1H-NMR (DMSO-d6) delta: 10.89 (1H, s), 8.88 (1H, d, J=2.0 Hz), 8.80 (1H, d, J=2.0 Hz), 8.73 (1H, d, J=2.0 Hz), 8.48 (1H, d, J=2.0 Hz), 8.27 (1H, d, J=9.2 Hz), 7.79 (1H, d, J=9.2 Hz), 3.09-3.00 (1H, m), 1.32 (6H, d, J=6.6 Hz). MS m/z (M+H): 344.

1309774-03-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1309774-03-5 ,7-Bromo-2-chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

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