Month: November 2020

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.,1569-16-0

A solution of selenium dioxide (8.61 g, 77.56 mmol) in 1,4 dioxane (140 mL) with 0.5 mL ofwater was stirred at 100 ¡ãC for 5 mm. The mixture was cooled down to 0 ¡ãC and 2-Methyl-I ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at100 ¡ãC for 5 h. Completion of the reaction was monitored by TLC. The reaction mixturewas filtered through celite bed, washed with EtOAc (50 mL) and concentrated. Theresulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brownsolid). 1H NMR (300 MHz, DMSO-d6): 6 10.18 (5, IH), 9.28-9.27 (m, IH), 8.74 (d, J = 8.1 Hz, IH), 8.63 (d, J= 8.1 Hz, IH), 8.11 (dd, J= 8.4, 1.2 Hz, IH), 7.83-7.79 (m, IH). LCMS:(Method B) 159.0 (M +H), Rt. 2.44 mm, 91 .59percent (Max). HPLC: (Method B) Rt 2.41 mm, 87.86percent (Max).

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

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 1,5-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 254-79-5, its synthesis route is as follows.,254-79-5

Preparation 63-Bromo-[1 ,5]naphthyridine[00123] [1 ,5]Naphthyridine (200 mg, 1.53 mmol) is dissolved in 2 ml_ of acetic acid, sodium acetate (300 mg, 3.07 mmol) is added, the mixture is heated to 85 0C and a solution of bromine (0.087 ml_, 270 mg, 1.69 mmol) in 0.3 ml_ acetic acid is added dropwise. The mixture is heated for 3 h, cooled and evaporated to dryness. The residue is purified by flash column chromatography to give 65 mg of title compound along with dibrominated product.

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

Reference£º
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

As a common heterocyclic compound, it belong naphthyridine compound,2-Methyl[1,8]-Naphthyridine,1569-16-0,Molecular formula: C9H8N2,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

A stirred solution of 2-methyl-1,8-naphthyridine (57.5 g, 399 mmol) (available from Manchester Organics) and (R)-tert-butyl 3-(iodomethyl)pyrrolidine-1-carboxylate (124.2 g, 399mmcl) (Intermediate 1) in THF (1 L) was cooled to 0 ¡ãC and treated under nitrogen with a solution of lithium bis(trimethylsilyl)amide in THE (1M, 399 mL, 399 mmcl) over 20 mm and the reaction mixture was stirred at 0 ¡ãC for 3 h. The reaction was quenched with saturated ammonium chloride solution (500 mL) and water (500 mL) and ethyl acetate (1 L) was added. The layers were separated and the aqueous phase was extracted with further ethyl acetate (1 L). The combinedorganic layers were dried (MgSO4), filtered and evaporated in vacuo. The residual brown oil (162 g) was purified by chromatography on a silica cartridge (750 g) eluting with a gradient of 0 ? 100percent [ethyl acetate in (5percent MeOH ? 95percent ethyl acetate)] over 8 column volumes. The appropriate fractions were combined and evaporated in vacuo to give the title compound (46.65 g, 36percent) as an orange solid: LCMS (System A) RT=0.99 mm, 97percent, ES+ve m/z328 (M+H)?, [aiD2¡ã = + 22 (c 1.00in EtOH).

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; CAMPBELL, Ian Baxter; CAMPBELL-CRAWFORD, Matthew Howard James; HANCOCK, Ashley Paul; LEMMA, Seble; MACDONALD, Simon John Fawcett; PRITCHARD, John Martin; PROCOPIOU, Panayiotis Alexandrou; (64 pag.)WO2016/46230; (2016); A1;,
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

General procedure: To a set of vials containing the requisite aryl halide(0.15 mmol) was added a solution of Bi (30 mg, 0.073 mmol) in THF (1.0 mL). The vials werecapped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vialwas drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added DCM (1 mL) and TFA (0.5 mL). The mixtures were stirred at RT for 2 hours. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) andfiltered. The crude products were purified by mass triggered preparative HPLC [Waters Sunfire C18 column, Sum, 19×100 mm, using a gradient from 10% initial to 40% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 mm run timej to afford Examples 22-23.

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; SCOTT, Jack, D.; BLIZZARD, Timothy, A.; WALSH, Shawn, P.; CUMMING, Jared, N.; (105 pag.)WO2017/95759; (2017); 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.100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

7-F4- (2-HVDROXVETHYLIDENE) PIPERIDIN-1-YLL-1-CVCLOPROPVL-6-FLUORO-4-OXO-1, 4- DIHVDRONAPHTHYRIDINE-3-CARBOXVIIC acid (163) A solution of amine 103 (256 mg, 1.06 MMOL) and triethylamine (0.5 mL, 3.55 MMOL) in ACETONITRILE (4 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4-dihydro-naphthyridine-3- carboxylic acid (200 mg, 0.71 MMOL) under nitrogen and the reaction mixture was allowed to stir for 16 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3 x 10 mL) and allowed to dry overnight to afford the title compound 163 (105 mg, 40%). MS 374 (M+H)., 100361-18-0

100361-18-0 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid 11055142, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.,100361-18-0

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolydine dimethanesulfonate (12. 5g) and 1-naphthaldehyde (11. lg) were in turn introduced into a reaction vessel at room temperature and cooled to 0~5 C. Triethylamine (12.2g) was dropwise added to the reaction mixture. After stirring the mixture for about 0. 5h, the reaction mixture was diluted by adding ethanol (30ml). 7-Chloro-l-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo- 1, 8-naphthyridine-3-carboxylic acid (lO. Og) was introduced to the reaction mixture. After raising slowly the reaction temperature to room temperature, the reaction mixture was stirred for about 15h. The title compound in the form of solid was filtered, washed with water and ethanol, and dried to prepare 15.7 g of the title compound (Yield: 84. 4%). 1H NMR (o, CDCl3) : 8.86 (m, 2H), 8.55 (s, 1H), 7. 82 (m, 3H), 7.73 (m, 1H), 7.40 (m, 3H), 4.60 (m, 2H), 4.24 (m, 2H), 4.08 (m, 1H), 3.99 (m, 1H), 3.95 (s, 3H), 3.45 (m, 2H), 1.13 (m, 2H), 0. 89 (m, 2H) Mass (FAB): 528 (M+H)

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,belong naphthyridine compound

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2003/87100; (2003); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

l-(2-(7-methoxy-l,5-naphthyridin-4-ylamino)ethyl)-5-(thiophen-2- yl)pyridin-2(lH)-one.; A suspension of 8-chloro-3-methoxy-l,5-naphthyridine (35 mg, 182 mumol) and l-(2-aminoethyl)-5-(thiophen-2-yl)pyridin-2(lH)-one (40 mg, 182 mumol) in iPrOH (0.5mL) was heated to 100C overnight. The mixture was partitioned between CH2Cl2 (10 mL) and IM NaOH (5mL). The aqueous was further extracted with CH2Cl2 (2x 5mL) and combined organics dried over MgSO4 then purified on silica (12 g) eluting with 15-60% of 5% (MeOH/ CH2Cl2). MS (ESI pos. ion) m/z (MH+): 379. Calc’d exact mass for C20H18N4O2S: 378. 1H NMR (400 MHz, Chloroform-d) delta ppm 3.09 (br. s., 1 H) 3.85 (q, J=6.13 Hz, 2 H) 3.93 (s, 3 H) 4.28 (t, J=5.97 Hz, 2 H) 6.57 (d, J=5.48 Hz, 1 H) 6.65 (d, J=9.59 Hz, 1 H) 6.81 (d, J=2.74 Hz, 1 H) 6.91 – 7.00 (m, 2 H) 7.10 – 7.15 (m, 1 H) 7.34 (d, J=2.54 Hz, 1 H) 7.50 – 7.58 (m, 2 H) 8.40 (d, J=2.74 Hz, 1 H) 8.45 (d, J=5.48 Hz, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

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

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).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,7-Naphthyridin-2(1H)-one, and cas is 54920-82-0, its synthesis route is as follows.,54920-82-0

To a suspension of 6.0 g of 1,7-naphthyridin-2(1H)-one in 60 mL of N,N-dimethylformamide, 2.5 g of 60percent sodium hydride was added at room temperature, and the mixture was stirred at 50 to 60¡ãC for 1 hour. Thereto was added 6.4 mL of 2-bromomethyl-1,3-dioxolan, the temperature was increased to 90 to 95¡ãC, and the reaction mixture was stirred for 2 hours 30 minutes. The temperature was further increased to 95 to 100¡ãC, and the mixture was stirred for 4 hours. Thereto were added 0.82 g of 60percent sodium hydride and 2.1 mL of 2-bromomethyl-1,3-dioxolan and the mixture was further stirred at the same temperature for 2 hours. Thereto were added 0.49 g of 60percent sodium hydride and 1.3 mL of 2-bromomethyl-1,3-dioxolan and the mixture was stirred at 90 to 100¡ãC for 2 hours. Thereto were further added 0.49 g of 60percent sodium hydride and 1.3 mL of 2-bromomethyl-1,3-dioxolan and the mixture was stirred at the same temperature for 4 hours. The reaction mixture was cooled to 5¡ãC, and ethyl acetate and ice water were then added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate = 100:0 to 0:100 and then, using gradient elution with chloroform:methanol = 100:0 to 90:10 to obtain 3.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,7-naphthyridin-2(1H)-one as a brown solid. 1H-NMR (CDCl3) delta: 3.85-3.94 (2H, m), 3.99-4.08 (2H, m), 4.58 (2H, d, J = 4.5 Hz), 5.29 (1H, t, J = 4.5 Hz), 6.91 (1H, d, J = 9.4 Hz), 7.41 (1H, d, J = 5.1 Hz), 7.67 (1H, d, J = 9.4 Hz), 8.45 (1H, d, J = 5.1 Hz), 9.05 (1H, s)

With the complex challenges of chemical substances, we look forward to future research findings about 54920-82-0,belong naphthyridine compound

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem