Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15992-83-3,1,8-Naphthyridin-2-amine,as a common compound, the synthetic route is as follows.,15992-83-3

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.

As the paragraph descriping shows that 15992-83-3 is playing an increasingly important role.

Reference£º
Patent; Rhone-Poulenc S.A.; US3948917; (1976); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

6-Bromo-1,8-naphthyridin-2-ol, cas is 72754-05-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

72754-05-3, Step 1: A mixture of 6-bromo-i,8-naphthyridin-2(1H)-one (1.0 equiv) and 2,5-dihydrofuran (10 equiv) in AcOH (0.05 M) was irradiated with UVA lamps (Rayonet reactor, RPR3 500 A bulbs) at RT overnight. The mixture was filtered, washing with EtOAc, and the solids were dried in vacuo. The so-obtained residue was purified via flash chromatography over silica gel, eluting with DCM and 0-20% EtOAc gradient to provide the title (rac)-2-bromo- 6a,6b,7,9,9a,9b-hexahydrofuro[3 ?,4?: 3 ,4]cyclobuta[ 1,2-c] [1 ,8]naphthyridin-6(5H)-one as a yellow solid in 9% yield. ?H NIVIR (400 IVIHz, DMSO-d6) oe 10.60 (s, 1H), 8.20 (m, 1H), 7.85 (m, 1H), 4.13 (d,J= 9.4 Hz, 1H), 3.97 (d,J= 9.6 Hz, 1H), 3.38 (m, 3H), 3.06 (d,J 8.9, 5.1 Hz, 1H), 2.90 (dd, J= 9.7, 4.4 Hz, 1H), 2.84 (m, 1H). LCMS (m/z) (M+H) = 295.1/297.1, Rt = 0.69 mm.

As the rapid development of chemical substances, we look forward to future research findings about 72754-05-3

Reference£º
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1. Ethyl 1- (2, 4-difluorophenyl)-6-fluoro-4-oxo-7- (piperazin-1-yl)-1, 4-dihydronaphthyridine-3- carboxylate: Ethyl 7-chloro-1- (2, 4-difluorophenyl)-6-fluoro-4-oxo-1, 4-dihydronaphthyridine- 3-carboxylate (766 mg, 2.0 mmol) and piperazine (430 mg, 5. 0 mmol, 2.5 equiv) were dissolved in 20 mL of pyridine and allowed to stir at room temperature for 24 h. The solvent was removed in vacuo, and the crude product was taken up in CH2C12, washed with 5% aq Na2CO3, then water. The organic layer was dried (Na2SO4), evaporated in vacuo, and the resulting white solid was purified on silica gel column using a linear gradient (100% CH2C12 to 10% MeOH in CH2C12) to give a white solid. ESI MS m/z 433 (M+H+), 887 (2M+Na+) ; IH NMR (400 MHz, CDC13) : 8 8. 94 (s, 1H, quinolone), 8.12 (d, J= 12. 5 Hz, 1H, quinolone), 7.39 (app dd, J= 13. 3 Hz, 7.04 Hz, 1H, Ph), 7.26 (s, 1H, Ph), 7.04 (app q, J= 15. 7, 8. 6 Hz, 1H, Ph), 4.36 (q, J= 7.0, 2H, Et), 3.50 (app t, J= 4.7 Hz, 4H, piperazine), 2.87 (app t, J= 4.7 Hz, 4H, piperazine), 1. 38 (t, J= 7.0 Hz, 3H, Et)., 100491-29-0

100491-29-0 Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 1268243, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; CUMBRE INC.; WO2005/70940; (2005); 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.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

952059-69-7, Example 103; 2-(2-(7-Methoxy-l,5-naphthyridin-4-ylamino)ethyl)-6-(4-methylthiophen-2- yl)pyridazin-3(2H)-one. A suspension of 2-(2-aminoethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (360 mg, 1530 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (298 mg, 1530 mumol) in iPrOH (5 mL) was heated to 100 C in a sealed vial. After 3 h, the reaction mixture was partitioned between CH2Cl2 (30 mL) and IM NaOH (10 mL). The organic layer was dried over MgSO4, concentrated to a solid, and purified on 40 gram of silica eluting with 0-60% of 6% (2M NH3 in MeOH)/ CH2Cl2. The resulting oil was crystalized from ACN (0.5 mL). MS (ESI pos. ion) m/z (MH+): 394. Calc’d exact mass for C20Hi9N5O2S: 393. 1H NMR (400 MHz, Chloroform-d) delta ppm 2.28 (s, 3 H) 3.84 (q, J=6.06 Hz, 2 H) 3.93 (s, 3 H) 4.55 (t, J=6.06 Hz, 2 H) 6.56 (d, J=5.48 Hz, 1 H) 6.93 – 6.98 (m, 2 H) 7.02 (t, J=5.67 Hz, 1 H) 7.16 (d, J=I .17 Hz, 1 H) 7.46 (d, J=2.74 Hz, 1 H) 7.52 (d, J=9.78 Hz, 1 H) 8.40 (d, J=2.74 Hz, 1 H) 8.46 (d, J=5.28 Hz, 1 H).

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; AMGEN INC.; WO2008/103277; (2008); A2;,
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

2-chloro-1,5-naphthyridine (101 mg, 0.614 mmol), boronate ester R1 (195 mg, 0.920 mmol), S-Phos (25.2 mg, 0.061 mmol), K3PO4 (391 mg, 1.841 mmol) and PdOAc2 (6.89 mg, 0.031 mmol) were combined in a 5-mL microwave vial in THF (2.5 mL) and water (500 mul). The reaction mixture was heated at 100 C for 15 min. The reaction mixture was diluted with EtOAc (20 mL), washed with sat. aq. NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4 filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (10 to 100% EtOAc in hexanes) to afford the title compound as a pale orange solid (118 mg, 90%). 1H NMR (500 MHz, DMSO): delta 9.02 (dd, J = 4.1, 1.6 Hz, 1 H), 8.48 (d, J = 8.8 Hz, 1 H), 8.48-8.42 (m, 1 H), 8.25 (d, J = 8.7 Hz, 1 H), 7.84-7.79 (m, 2 H), 7.13 (d, J = 16.0 Hz, 1 H), 4.25 (q, J = 7.1 Hz, 2 H), 1.30 (t, J = 7.1 Hz, 3 H) ppm; LRMS m/z (M+H) 229.2 found, 229.1 required.

The synthetic route of 7689-62-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Sharp & Dohme Corp.; BRESLIN, Michael J.; COX, Christopher D.; HARTINGH, Timothy J.; PERO, Joseph; RAHEEM, Izzat T.; ROSSI, Michael; VASSALLO, Laura; (89 pag.)EP2714041; (2016); B1;,
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: (Method C2) Synthesis of 4-(4-tert-butylphenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine In a nitrogen purged sealed tube, 8-chloro-3-methoxy-1,5-naphthyridine (0.053 g, 0.271 mmol) was dissolved in DMF (2.00 mL). 4-(4-(4-Tert-butylphenyl)phthalazin-1-ylamino)phenol (0.100 g, 0.271 mmol) and cesium carbonate (0.176 g, 0.541 mumol) were added, and the mixture in the tube was stirred at 90 C. for 17 h. Upon cooling to RT, the mixture was concentrated in vacuo, and purified by silica gel chromatography using 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2 to yield 4-(4-tert-butylphenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine as off-white solid. MS [M+H]=528.1; Calc’d 527.6 for C33H29N5O2.

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

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

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,1569-16-0

The mixture of 2-methyl-l,8-naphthyridine (85 mg, 0.586 mmol), E25A (128 mg, 0.586 mmol), and 4-methylbenzenesulfonamide (100 mg, 0.586 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by reverse phase ISCO (26 g C18 30 min gradient from 100percent A: 0percent B to 0percent A: 100percent B (A = 90percent H2O/10 percent ACN + 0.1percent TFA); (B = 90percent ACN/10percent H2O + 0.1percent TFA); detection at 220 nm) to yield E25B (18 mg, 5percent) as a minor byproduct. LCMS (ES): m/z 516.2 [M+H]+.

The synthetic route of 1569-16-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); 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

Method N B-9 Ex. 3 To a stirred solution of Intermediate B-9 (400 mg, 0.937 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (252 mg, 1.03 mmol) in THF (10 mL) was added LHMDS (1 M in THF, 3.28 mL, 3.28 mmol) at RT. The mixture was stirred at 45 C overnight, quenched with NH CI (sat.) and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The residue was treated with 5 mL of DCM and 0.5 mL of TFA and stirred at 25 C for 2 h. The mixture was neutralized with NaHC03 and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica column chromatography (PE: EtOAc = 1 : 1) to afford example 3. MS for example 3: m/e = 533 and 535 (M+l)., 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; 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

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

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

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

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

0385-7 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (142 mg), bis(pinacolato)diboron (223 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (47 mg), potassium acetate (115 mg), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(3-(3-ethyl-4-iodo-1H-pyrazol-1-yl)propyl)morpholine (204 mg), sodium carbonate (124 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (41 mg), and water (0.3 mL) were added thereto, followed by stirring at 80 C. for 4 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-ethyl-1H-pyrazol-1-yl)propyl)morpholine (18 mg). MS m/z (M+H): 386., 1309774-03-5

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