Extracurricular laboratory: Synthetic route of 100491-29-0

100491-29-0, As the rapid development of chemical substances, we look forward to future research findings about 100491-29-0

Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A. Method I: 560 mg (5mmol) of 1,4-diazabicyclo[2.2.2]octane and 890 mg (5.3 mmol) of 90% pure 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole are added to 1.9 g (5 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate in 20 ml of acetonitrile. The mixture is stirred at room temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 80 ml of water. The undissolved residue is filtered off with suction, washed with water and dried. Yield: 1.6 g (64% of theory) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylate, melting point: 173-176 C. (with decomposition)

100491-29-0, As the rapid development of chemical substances, we look forward to future research findings about 100491-29-0

Reference£º
Patent; Bayer Aktiengesellschaft; US5464796; (1995); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Extracurricular laboratory: Synthetic route of 15944-34-0

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

7-Chloro-1,8-naphthyridin-2-ol, cas is 15944-34-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

To a solution of 7-chloro-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1.80 g, 10.0 mmol) and 2- bromo-1 , 1-diethoxyethane (4.92 g, 25.0 mmol) in DMF (25 mL) was added Cs2C03 (4.90 g, 15.0 mmol) and the mixture heated at 70C under N2 overnight. The mixture was diluted with H2O (200 mL), extracted with EtOAc (100 mL x 3) and the combined organic extracts were washed with H2O (200 mL x 2), brine (100 mL) and concentrated under reduced pressure. The residue was purified by chromatography (EtOAc/petroleum ether, 1 :5 to 1 :2, v/v) to afford a white solid of 7-chloro-1-(2,2-diethoxyethyl)-1 ,2-dihydro-1 ,8-naphthyridin-2- one 5a (1.80 g, 61 %). TLC: Rf = 0.45 (silica gel, petroleum ether/EtOAc = 2 : 1 , v/v). 1 H NMR (Method E) (CDC ): delta ppm 7.78 (d, J = 8.0 Hz, 1 H), 7.61 (d, J = 9.6 Hz, 1 H), 7.15 (d, J = 8.0 Hz, 1 H), 6.72 (d, J = 9.6 Hz, 1 H), 5.10 (t, J = 5.6 Hz, 1 H), 4.67 (d, J = 5.6 Hz, 2H), 3.79 (m, 2H), 3.54 (m, 2H), 1.1 1 (t, J = 7.2 Hz, 6H).

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

Reference£º
Patent; REDX PHARMA PLC; COOPER, Ian; LYONS, Amanda; (102 pag.)WO2017/137743; (2017); A1;,
1,8-Naphthyridine – Wikipedia
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Extracurricular laboratory: Synthetic route of 15992-83-3

15992-83-3, As the rapid development of chemical substances, we look forward to future research findings about 15992-83-3

1,8-Naphthyridin-2-amine, cas is 15992-83-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Preparation of 5,7-dioxo-6-(1,8-naphthyridin-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (16.0 g.), m.p. 200 C., by reacting 2-amino-1,8-naphthyridine (8.65 g.) with 5,6-dihydro-1,4-dithiine-2,3-dicarboxylic acid anhydride (22.0 g.) [prepared according to the method of H. R. Schweizer, Helv. Chim. Acta, 52, 2229 (1969)] in diphenyl ether (70 cc.) at 150 C. for half an hour, in the presence of anhydrous acetic acid (0.4 cc.). Preparation of 5-hydroxy-6-(1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (13.0 g.), m.p. 260 C., by reacting sodium borohydride (2.15 g.) with 5,7-dioxo-6-(1,8-naphthyridin-2-yl)-2,3,6,7-tetrahydro-1,4-dithiino[2,3-c]pyrrole (18.0 g.) in anhydrous tetrahydrofuran (200 cc.) to which anhydrous methanol (80 cc.) has been added gradually, at a temperature not exceeding 40 C.

15992-83-3, As the rapid development of chemical substances, we look forward to future research findings about 15992-83-3

Reference£º
Patent; Rhone-Poulenc S.A.; US3948917; (1976); A;,
1,8-Naphthyridine – Wikipedia
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Extracurricular laboratory: Synthetic route of 35192-05-3

35192-05-3, As the rapid development of chemical substances, we look forward to future research findings about 35192-05-3

2-Chloro-1,7-naphthyridine, cas is 35192-05-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Step B: Preparation of [N- (4-TERT-BUTYL-PHENYL)-2- ( [1, 7]] naphthyridin-2-ylamino)-benzamide A mixture of [2-AMINO-N- (4-TERT-BUTYL-PHENYL)-BENZAMIDE] (Step A, 163 mg, 0.61 mmol), [2-CHLORO- [1,] 7] naphthyridine [(100] mg, 0.61 [MMOL),] [PD2 (DBA)] 3 (6.0 mg, 0. [006] mmol), 2- dicyclohexyl [PHOSPHINO-2′- (N-N-DIMETHYAMINO)] biphenyl (6.0 mg, 0.015 mmol), and LiN (TMS) 2 (1 M solution in THF, 2.3 mL) was heated at [80 C] for 12 h in a sealed tube. The mixture was concentrated in vacuo and the crude material was purified with flash chromatography [(SI02,] [20%] EtOAc/hexane) and crystallization from EtOH to give the desired compound. MS [(ES+)] : [397.] 0 (M+H) [+.] Calc’d for [C25H24N4O-396.] 48.

35192-05-3, As the rapid development of chemical substances, we look forward to future research findings about 35192-05-3

Reference£º
Patent; AMGEN INC.; WO2004/5279; (2004); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Extracurricular laboratory: Synthetic route of 96568-07-9

As the rapid development of chemical substances, we look forward to future research findings about 96568-07-9

Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 96568-07-9, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

96568-07-9, Example 109 7-(4-chloro-2-isoindolinyl)-1-cyclopropyl-6-flurro-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid STR325 310 mg of 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4- oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 660 mg of 4-chloroisoindoline, 0.42 ml of triethylamine, and 5 ml of anhydrous chloroform were processed in the same manner as in Example 107 to produce 75 mg of 7-(4-chloro-2- isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8- naphthyridine-3-carboxylic acid. Melting point: above 300 C. 1 H-NMR (DMSO-d6) delta: 8.68 (1H, s, C2 –H), 8.06 (1H, d, C5 –H), 7.45-7.55 (3H, m, ARM-H), 5.3 (4H, br, s, 2 x–CH2 N–), 3.83 (1H. m, STR326 1.10-1.40 (4H, m, STR327

As the rapid development of chemical substances, we look forward to future research findings about 96568-07-9

Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5026856; (1991); A;,
1,8-Naphthyridine – Wikipedia
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Simple exploration of 959558-28-2

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

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

EXAMPLE 32: Synthesis of 4-[2-(2-fluoro-phenyl)-[1 ,8]naphthyridin-4-yl]-[2,7]naphthyridin- 1- C/MS: 1.40, [M+H] 368

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

Reference£º
Patent; MERCK PATENT GMBH; JONCZYK, Alfred; DORSCH, Dieter; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2011/95196; (2011); A1;,
1,8-Naphthyridine – Wikipedia
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Downstream synthetic route of 215523-34-5

As the paragraph descriping shows that 215523-34-5 is playing an increasingly important role.

215523-34-5, 1,8-Naphthyridine-2-carboxylic acid is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,215523-34-5

PyBOP (132 mg, 254 muiotaetaomicronIota) was added to a mixture of 1 ,8-naphthyridine-2-carboxylic acid (40.2 mg, 231 muiotaetaomicronIota), 8-amino-2-(2-chloro-4,5-difluorophenyl)-2-azaspiro[4.5]decan-1 -one (isomer 1 , Intermediate I45 ) (80.0 mg, 254 muiotaetaomicronIota) and N,N-diisopropylethylamine (160 muIota, 920 muiotaetaomicronIota) in DMF (2.3 ml) and the mixture was stirred for 2 h at room temperature. For work-up, water (45 ml) and methanol (2 ml) were added and the mixtre was stirred over night. The precipitate was collected by filtration, washed with water and dried to give the title compound 87.0 mg (79 % yield). LC-MS (Method 1 ): Rt= 1.08 min; MS (ESIpos): m/z = 471 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.932 (1.28), 0.949 (1.24), 1.231 (1.28), 1.352 (0.85), 1.591 (0.43), 1.634 (0.73), 1.657 (3.54), 1.665 (3.07), 1.689 (16.00), 1.696 (15.91), 1.732 (4.05), 1.742 (3.41), 1.761 (3.46), 1.772 (3.11), 1.791 (1.62), 1.801 (1.37), 1.855 (5.29), 1.877 (3.07), 1.886 (2.69), 2.069 (0.43), 2.155 (7.04), 2.172 (13.78), 2.190 (7.51), 2.337 (0.81), 2.518 (9.26), 2.523 (6.53), 2.674 (1.79), 2.679 (0.81), 2.888 (0.47), 3.612 (0.51), 3.639 (7.59), 3.656 (13.87), 3.674 (7.34), 3.871 (0.73), 3.897 (1.75), 3.908 (1.66), 3.919 (1.75), 3.946 (0.73), 7.697 (5.21), 7.717 (5.72), 7.724 (5.59), 7.732 (9.13), 7.743 (11.05), 7.753 (8.02), 7.763 (9.30), 7.863 (5.38), 7.884 (5.63), 7.889 (5.80), 7.910 (5.63), 8.264 (15.15), 8.285 (15.66), 8.580 (7.55), 8.586 (7.89), 8.601 (7.64), 8.606 (7.17), 8.680 (15.27), 8.701 (13.82), 8.822 (6.10), 8.844 (5.89), 9.197 (8.96), 9.202 (9.17), 9.208 (8.41), 9.212 (7.94)

As the paragraph descriping shows that 215523-34-5 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Simple exploration of 1309774-03-5

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

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,1309774-03-5

0421-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (48 mg), bis(pinacolato)diboron (58 mg), a 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride-dichloromethane complex (16 mg), potassium acetate (42 mg), and 1,4-dioxane (1.9 mL) was stirred at 100 C. for 2 hours. N-(4-bromopyridin-2-yl)acetamide (42 mg), sodium carbonate (45 mg), a bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (14 mg), 1,4-dioxane (0.3 mL), and water (0.19 mL)) were added to the reaction mixture, followed by stirring at 100 C. for 2 hours. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining N-(4-(6-chloro-1,5-naphthyridin-3-yl)pyridin-2-yl)acetamide (12.6 mg) as a pale brown solid. MS m/z (M+H): 299.

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

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

Downstream synthetic route of 1569-16-0

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

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

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

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

Downstream synthetic route of 1309774-03-5

As the paragraph descriping shows that 1309774-03-5 is playing an increasingly important role.

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,1309774-03-5

0540-1 A suspension of 7-bromo-2-chloro-1,5-naphthyridine (44 mg), 1-(4-aminopiperidin-1-yl)ethanone (26 mg), tris(dibenzylideneacetone)dipalladium(0) (15 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (30 mg), and sodium tert-butoxide (50 mg) in 1,4-dioxane (2 mL) was stirred at 80 C. for 4 hours. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (methanol-ethyl acetate), thereby obtaining 1-(4-((6-chloro-1,5-naphthyridin-3-yl)amino)piperidin-1-yl)ethanone (8.1 mg). MS m/z (M+H): 305.

As the paragraph descriping shows that 1309774-03-5 is playing an increasingly important role.

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