Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,952059-69-7

Under an atmosphere of argon, a mixture of 4-chloro-7-methoxy-l,5-naphthyridine (1 g), methyl 2-(4-hydroxy-2-methoxyphenyl)acetate (1.01 g), caesium carbonate (5.02 g) and DMF (10 ml) was stirred and heated to 1000C for 3 hours. The resultant mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate and methanol as eluent. There was thus obtained methyl 2-[2-methoxy-4-(7-methoxy-l,5-naphthyridin- 4-yloxy)phenyl]acetate (1.23 g); 1H NMR Spectrum: (DMSOd6) 3.63 (s, 3H)5 3.65 (s, 2H)5 3.76 (S5 3H)5 4.0 (s, 3H)5 6.75 (m, 2H), 6.95 (d, IH), 7.3 (d, IH), 7.79 (d, IH)5 8.72 (m, 2H); Mass Spectrum: M+H+ 355.

The synthetic route of 952059-69-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

A common heterocyclic compound, the naphthyridine compound, name is 2-Chloro-1,5-naphthyridine,cas is 7689-62-5, mainly used in chemical industry, its synthesis route is as follows.

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.

As the rapid development of chemical substances, we look forward to future research findings about 7689-62-5

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

15944-34-0, 7-Chloro-1,8-naphthyridin-2-ol is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,15944-34-0

10. i. 7-methoxy-lH-[l, 8]naphthyridin-2-one:To a solution of 7-chloro-lH-[l,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 niL) was added sodium methoxide (25 wt% in MeOH, 161 mL). The resulting solution was stirred at reflux for15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added.The phases were separated and the aq layer was extracted with EA (8 x 80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid(5.22 g, 100% yield).1H NMR (d6DMSO) delta: 11.96 (s, 1eta); 7.96 (d, J = 8.5 Hz, IH); 7.81 (d, J = 9.4 Hz, IH); 6.63 (d, J = 8.5 Hz, IH); 6.34 (d, J = 9.4 Hz, IH); 3.90 (s, 3H).

The synthetic route of 15944-34-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/147616; (2009); 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

Synthesis of 2-[1-(2-tert-butyl-6-chloro-5-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridine 20 ml of dimethylacetamide and 5 ml (17.8 mmoles) of diisopropylethylamine are added into a single-necked flask containing 1.5 g (6.84 mmoles) of 2-tert-butyl-4,6-dichloro-5-methyl-pyrimidine and 1.46 g (6.84 mmoles) of 2-piperidin-4-yl-[1,8]naphthyridine. This mixture is heated at 100 C. overnight. The next day 0.2 equivalent of naphthyridine is added and the mixture is heated for another 6 hours. The reaction mixture is returned to ambient temperature before concentrating to dryness. The residue obtained is taken up in a mixture of water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The collected organic phases are dried over magnesium sulphate then the solvent is evaporated off under reduced pressure (2 kPa). The residue is chromatographed on silica gel eluding with a gradient of heptane-ethyl acetate (70-30) to heptane-ethyl acetate (50-50). 1.77 g of expected product is obtained. TLC: Rf=0.50 [silica gel, eluent heptane-ethyl acetate (50-50). 1H-NMR (CDCl3): delta 1.37 (s, 9H, tert-butyl); 2.1 (m, 1H, cyclopropyl); 2.15 (m, 4H, N-CH2–CH–CH2); 2.27 (s, 3H, CH3); 3.1 and 4.05 (2m, 4H, CH2–N–CH2); 3.25 (m, 1H, N-CH2-CH2–CH2-CH2); [(7.48; 8.18; 9.12), 3m, 5H, naphthyridine]. MS: 396 (MH+).

As the paragraph descriping shows that 254-60-4 is playing an increasingly important role.

Reference£º
Patent; Proskelia SAS; US2008/58348; (2008); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

17965-71-8, 3-Bromo-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,17965-71-8

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]+.

The synthetic route of 17965-71-8 has been constantly updated, and we look forward to future research findings.

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

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,952059-69-7

General procedure: Example 17 Synthesis of 4-(7-methoxy-1,5-naphthyridin-4-ylthio)benzenamine A RBF was charged with 4-aminothiophenol (161 mg, 1.285 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (250 mg, 1.285 mmol) and 5.2 mL of DMF, and the mixture was stirred at RT for 45 min. The orange, heterogeneous mixture was diluted with EtOAc and washed with 1N NaHCO3. The aqueous portion was extracted two additional times with EtOAc and the combined organics were dried with MgSO4, filtered and concentrated. The crude oil was concentrated twice from toluene to remove DMF and the resulting solids were dried under high vacuum to provide 4-(7-methoxy-1,5-naphthyridin-4-ylthio)benzenamine as a tan solid. MS m/z=284 [M+H]+. Calc’d for C15H13N3OS: 283.35.

952059-69-7 8-Chloro-3-methoxy-1,5-naphthyridine 59427340, anaphthyridine compound, is more and more widely used in various fields.

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

1260670-05-0, 3-Bromo-8-chloro-1,7-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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%)., 1260670-05-0

1260670-05-0 3-Bromo-8-chloro-1,7-naphthyridine 72213592, anaphthyridine compound, is more and more widely used in various fields.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35192-05-3,2-Chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

2-Chlorb-[l,7]naphthyridine (100 mg, 0.61 mmol) , 2-amino-N- (4- tert-butyl-phenyl) -benzamide (164 mg, 0.61 mmol),Pd2(dba)3 (6 mg, 0.006 mmol), (2 ‘ -Dicyclohexylphosphanyl-biphenyl – 2 -yl) -dimethyl -amine (6 mg, 0.015 mmol), and 1Msolution of LiN(TMS)2 in THF (1.83 inL) , 1.83 mmol) wereadded to a reaction vessel. The vessel was sealed and thereaction was stirred at 70 aC for 24h. The mixture wascooled to RT, and solvent was removed under vacuum. Thecrude was purified by flash column chromatography (gradiant,0 to 100% EtoAC/Hexane) to give the product as tan solid. MS(ES~) : 397.0 (M+H) + . Calc’d for C25H24N40 – 396.20., 35192-05-3

35192-05-3 2-Chloro-1,7-naphthyridine 20696625, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; WO2006/12374; (2006); 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.96568-07-9,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.,96568-07-9

EXAMPLE 64 Ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazole-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 4-(1,2,3-triazol-1-yl)piperidine hydrochloride (225 mg, 1.2 mmol) and DBU (182 mg, 1.2 mmol) was added to a suspension of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100 C. for 5 hrs. The suspended solid was filtered and the filtrate was concentrated to dryness. The residue was triturated with water and separated solid was filtered, washed with water and dried to give 135 mg of desired product. m.p. 213-214 C.; 1 H NMR (CDCl3) delta: 8.48 (s, 1H), 8.11 (d, 1H), 7.72 (s, 1H), 7.60 (s, 1H), 4.60-4.85 (m, 3H), 4.29-4.40 (q, 2H), 3.43-3.54 (m, 1H), 3.21-3.35 (m, 2H), 2.10-2.36 (m, 4H), 1.36 (t, 3H), 0.95-1.23 (m, 4H).

The synthetic route of 96568-07-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
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.54920-82-0,1,7-Naphthyridin-2(1H)-one,as a common compound, the synthetic route is as follows.,54920-82-0

To a solution of lH-l,7-naphthyridin-2-one (1.6 g, 11.0 mmol) in MeOH (50 mL) was added BnBr (2.1 g, 12.1 mmol) at to 70 ¡ãC. The resulting mixture was stirred at 70 ¡ãC for 3 hrs and then cooled to 0 ¡ãC. To the cooled mixture was added NaBH4 (2.09 g, 55.0 mmol). The resulting mixture was slowly warmed to rt and stirred for 3 hrs at rt. The reaction was quenched with 6N HC1 (20 mL). The resulting mixture was stirred at rt for 2 hrs, then basified with 2 N NaOH to pH 10 and extracted with DCM (50 mL) twice. The combined organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by column (eluting with DCM: MeOH =40:1, v:v) to give 7-benzyl-l,5,6,8-tetrahydro-l,7-naphthyridin-2-one (700 mg) as a yellow solid.

54920-82-0 1,7-Naphthyridin-2(1H)-one 589676, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem