Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

Step 1To a stirred solution of (R)-tert-butyl (5-(5-amino-2-fluorophenyl)-2,5 -dimethyl -1,1- dioxido-l,2,4-thiadiazinan-3-ylidene)carbamate A9 (250 mg, 0.647 mmol) and 3-bromo-8- chloro-l,7-naphthyridine (205 mg, 0.841 mmol) in THF (6.47 ml) was added LiHMDS (1M in THF, 1.617 ml, 1.617 mmol) at room temperature. The mixture was stirred at 45 C for 4h. It was diluted with saturated ammonium chloride and extracted with DCM (3x). The organics were combined, dried over magnesium sulfate, filtered and concentrated. The residue was redissolved in DCM (3 mL) and TFA (0.249 ml, 3.23 mmol) added and the reaction stirred for 15h. The reaction was quenched with saturated sodium bicarbonate and extracted with DCM (3x). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography EtOAc in DCM to afford example 2. MS for example 2: m/e = 493 (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.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WU, Wen-Lian; HE, Shuwen; WALSH, Shawn, P.; CUMMING, Jared, N.; (70 pag.)WO2016/118404; (2016); 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,1260670-05-0

General procedure: Parallel preparation of examples 6-7: To a set of vials containing the requisite aryl halide (0.20 mmol) was added a solution of HI (50 mg, 0.10 mmol) in THF (1.0 mL). The vials were capped 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, 0.25 mL, 0.25 mmol). 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 vial was 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 water (0.050 mL) and TFA (0.5 mL). The mixtures were stirred at 50C with stirring overnight. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude residue containing Example 6 was purified by mass triggered preparative HPLC. [column: Waters XBridge CI 8, 5mupiiota , 19×100 mm; solvent: gradient 35-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Example 6. The crude residue containing Example 7 was purified by mass triggered preparative HPLC [Waters Sunfire CI 8 column, 5muetaiota, 19 100 mm, using a gradient from 10% initial to 45% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 min run time] to afford Example 7.

The synthetic route of 1260670-05-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; SCOTT, Jack, D.; (65 pag.)WO2016/40226; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The naphthyridine compound, cas is 1309774-03-5 name is 7-Bromo-2-chloro-1,5-naphthyridine, mainly used in chemical industry, 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

With the rapid development of chemical substances, we look forward to future research findings about 1309774-03-5

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

The naphthyridine compound, cas is 1569-16-0 name is 2-Methyl[1,8]-Naphthyridine, mainly used in chemical industry, its synthesis route is as follows.

The starting material tert-butyl 7-(2-hydroxyethyl)-2-methyl-3,4-dihydro-l,8- naphthyridine-l(2H)-carboxylate was prepared as follows: To a stirred solution of 2-methylnaphthyridine (2.0 g, 13.9 mmol) in THF (5 ml) was added at -78¡ãC MeLi 1.6M (7.2 ml, 41.7 mmol) over 5 minutes. The reaction mixture was left to stir at -780C for 2 hours, then at room temperature for 2 hours. Then a careful5 hydrolysis at 0¡ãC with water was followed by extraction of the aqueous layer with diethyl ether. The organic layer was dried and concentrated to give 2,7-dimethyl-l,2-dihydro-l,8- naphthyridine as a red oil (1.98 g, 90percent); Mass Spectrum [M+H]+ = 161; 1H NMR Spectrum (DMSO-d6) 1.20 (d, 3H), 2.14 (s, 3H), 4.41-4.49 (m, IH), 5.46 (ddd, IH), 6.17 (dd, IH), 6.20 (d, IH), 6.44 (s, IH), 6.90 (d, IH)., 1569-16-0

With the rapid development of chemical substances, we look forward to future research findings about 1569-16-0

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/141473; (2007); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

The mixture of 2-methyl-l,8-naphthyridine (115 mg, 0.799 mmol), E6A (148 mg, 0.799 mmol), and 4-methylbenzenesulfonamide (137 mg, 0.799 mmol) in DME (10 mL) was heated at 170 ¡ãC under microwave conditions for 2 h. The mixture was purified by preparative HPLC (Phenomenex Luna Axia 5mu Omicron18 30 chi 100 mm; 10 min gradient from 85percent A: 15percent 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 E6B (170 mg, 68percent yield). LCMS (ES): m/z 312.2 [M+H]+.

1569-16-0, 1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various.

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

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

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]+., 1569-16-0

With the rapid development of chemical substances, we look forward to future research findings about 1569-16-0

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

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

Example 14; N-(l-ethyl-lJHr-pyrazol-4-yl)-2-[2-methoxy-4-(7-methoxy-l,5-naphthyridin- 4-yloxy)phenyl] acetamide; Under an atmosphere of argon, a mixture of 4-chloro-7-methoxy-l,5-naphthyridine (0.09 g), N-(l-ethyl-lH-pyrazol-4-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide (0.127 g), caesium carbonate (0.453 g) and DMF (1 ml) was stirred and heated to 900C for 7 hours. The mixture was cooled to ambient temperature and poured into water. The resultant mixture was filtered. The solid so obtained was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.12 g); 1H nuMR Spectrum: (DMSOd6) 1.32 (t, 3H)3 3.59 (s, 2H), 3.76 (s, 3H)5 4.0 (s, 3H), 4.07 (q, 2H)5 6.76 (d, IH), 6.77 (m, IH)5 6.94 (d, IH)5 7.31 (d, IH), 7.42 (s, IH), 7.79 (d, IH), 7.87 (s, IH)5 8.71 (d, IH)5 8.73 (d, IH)5 10.04 (s, IH); Mass Spectrum: M+?t 434.

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); 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.1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,as a common compound, the synthetic route is as follows.

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., 1260670-05-0

The synthetic route of 1260670-05-0 has been constantly updated, and we look forward to future research findings.

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

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

A. Ethyl 7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 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 are stirred with 680 mg (5.4 mmol) of [S,S]-2,8-diazabicyclo[4.3.0]nonane at 10 C. for 3 hours in 20 ml of acetonitrile and in the presence of 560 mg (5 mmol) of 1,4-diazabicyclo[2.2.2]octane. The suspension is filtered with suction, washed with water and dried. 0.35 g of product is obtained. By concentrating the mother liquors, stirring the residue with water, isolating the undissolved product and purifying by chromatography (silica gel, eluent: dichloromethane/methanol/17% strength aqueous ammonia), a further 0.7 g of product is isolated. Total yield: 1.05 g (44% of theory), Melting point: 184-185 C. (with decomposition), [alpha]D23: +6.8 (c=0.46, CHCl3)

100491-29-0, As the paragraph descriping shows that 100491-29-0 is playing an increasingly important role.

Reference£º
Patent; Bayer Aktiengesellschaft; US5480879; (1996); 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.7689-62-5,2-Chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,7689-62-5

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.133 g, 0.472 mmol), 2-chloro-1,5-naphthyridine (0.100 g, 0.608 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 mL, 1.437 mmol) was added and the reaction mixture was sealed under argon and heated at 100 C. for 59 h. The reaction was cooled to room temperature and partitioned between water/DCM. The aqueous layer was extracted with DCM (3*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco, (25 gram)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1?1:19) to give 67 mg (34%) of a white crystalline solid. ESI-MS 374.0 [M+1]. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.49 (dd, J=4.30, 1.56 Hz, 1H), 8.00 (d, J=3.33 Hz, 1H), 7.97 (d, J=3.33 Hz, 1H), 7.93 (d, J=9.19 Hz, 1H), 7.81-7.89 (m, 2H), 7.46 (dd, J=8.41, 4.11 Hz, 1H), 7.02 (d, J=9.19 Hz, 1H), 5.21 (m, 1H), 4.64-4.76 (m, 1H), 3.25-3.38 (m, 2H), 2.91-3.02 (m, 1H), 2.34-2.45 (m, 2H), 0.94-1.11 (m, 4H)

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

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem