Heterocyclic Building Blocks-Naphthyridine

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

2-(2-((7-Methoxy-l,5-naphthyridin-4-yl)(methyl)amino)ethyl)-6-(4- methylthiophen-2-yl)pyridazin-3(2H)-one. A suspension of 2-(2- (methylamino)ethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (275 mg, 1103 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (193 mg, 993 mumol) in iPrOH (5 mL) was heated to 100 C for 18 h in an appropriately sealed vial. The mixture was partitioned between CH2Cl2 (30 mL) and IM NaOH (10 mL), and the organic dried over MgSO4. After concentration under reduced pressure, the organic residue was dissolved in iPrOH (2 mL) and the rsulting crystalized solid was washed with iPrOH (2x 0.5 mL) then dried under reduced pressure. MS (ESI pos. ion) m/z (MH+): 408. Calc’d exact mass for C2ieta2iN5O2S: 407. 1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H) 3.22 (s, 3 H) 3.83 (s, 3 H) 4.51 (t, J=5.77 Hz, 2 H) 4.75 (t, J=5.77 Hz, 2 H) 6.55 (d, J=5.52 Hz, 1 H) 6.60 (d, J=9.54 Hz, 1 H) 6.91 (s, 1 H) 6.97 (s, 1 H) 7.19 (d, J=9.54 Hz, 1 H) 7.32 (d, J=3.01 Hz, 1 H) 8.32 (d, J=5.52 Hz, 1 H) 8.46 (d, J=2.51 Hz, 1 H).

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

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

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

Starting compound 5 (9.6g, 39.4mmol, 1eq),Vinylboronic acid pinacol ester (6.68g, 43.4mmol, 1.1eq),Sodium carbonate (20.9g, 197.1mmol, 5eq) was added to the THF-water (4: 1,480mL, 50V) mixed solvent,After nitrogen substitution, tetratriphenylphosphine palladium (911.2mg, 0.79mmol, 0.02eq) was added,After nitrogen replacement again, stirring and heating to reflux,After 1.5h, TLC and LCMS analyzed a small amount of raw materials remaining.After the heat was turned off, after the system was concentrated, the residue was extracted three times with EA, and the organic phases were combined,It was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and column chromatography (EA in Hep 15%),The product compound 6 was obtained as a light yellow solid 5.9 g, and the yield was 76.1%.

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Reference£º
Patent; Shanghai Changsen Pharmaceutical Co., Ltd.; Wang Zhe; Zhang Jiyong; Zeng Zhihong; (105 pag.)CN111039942; (2020); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

To a mixture of 10percent palladium on carbon (0.369 g, 0.347 mmol) in MeOH (20 mL) under nitrogen in a 500 mL Parr reaction vessel was added 2-methyl-l,8-naphthyridine (0.500 g, 3.47 mmol). The reaction mixture was vacuum flushed with nitrogen (3x), then with hydrogen (3x) and vigorously shaken under hydrogen at 60 psi at -25 ¡ãC for 23 h. The reaction was filtered through a pad of Celite and thoroughly washed with MeOH. The filtrated was concentrated in vacuo to afford a mixture of the title compounds (506.1 mg) as a white solid. NMR indicated a mixture of two products in a ratio of 1 :0.18 which was used without further purification. LC-MS retention time = 1.70 min; m/z = (0434) 149.06 [M+H]+. (Column: Phenomenex Luna CI 8 50 x 2.0 mm 3 muiotaeta. Solvent A = 90percent Water : 10percent MeOH : 0.1percent TFA. Solvent B = 10percent Water : 90percent MeOH : 0.1percent TFA. Flow Rate = 0.8 mL/min. Start percent B = 0. Final percent B = 100. Gradient Time = 4 minutes, then a 1 minute hold at 100percent B. Oven temperature = 40 ¡ãC. Wavelength = 220 nm). Major product: NMR (400 MHz, DMSO-d6) delta 6.99 (d, J=7.3 Hz, 1H), 6.24 (d, J=7.0 Hz, 1H), 6.21 (br s, 1H), 3.26 – 3.19 (m, 2H), 2.59 (t, J=6.3 Hz, 2H), 2.16 (s, 3H), 1.74 (dt, J=l 1.7, 6.0 Hz, 2H). Minor product: NMR (400 MHz, DMSO-d6) delta 7.76 – 7.69 (m, 1H), 7.12 (d, J=7.0 Hz, 1H), 6.39 (dd, J=7.2, 4.9 Hz, 1H), 3.49 – 3.33 (m, 1H), 2.70 – 2.61 (m, 2H), 1.89 – 1.78 (m, 1H), 1.47 – 1.33 (m, 1H), 1.15 (d, J=6.3 Hz, 3H).

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; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 0762 0762-1 60% sodium hydride (136 mg) was added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (300 mg), (4-methoxyphenyl)methanol, and N-methylpyrrolidone (12.3 mL) at a temperature of from 0 C. to 5 C., followed by stirring at room temperature for 2 hours in a nitrogen atmosphere. After water and ethyl acetate were added to the reaction mixture, the organic layer was washed sequentially with 0.01 mol/L hydrochloric acid and with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), thereby obtaining 7-bromo-2-((4-methoxybenzyl)oxy)-1,5-naphthyridine (204 mg) as a white solid. MS m/z (M+H): 345.

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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

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 suspension of 7-chloro-1 ,8-naphthyridin-2(1 H)-one (700 mg, 3.9 mmol) in MeOH (15 mL), NaOMe (25% solution in MeOH, 20 mL) was added. The resulting solution was stirred at reflux for 15 h then thesolvent was removed in vacuo. Water (100 mL) and EtOAc (80 mL) were added, the phases were separated and the aqueous layer was extracted with EtOAc (8 x 80 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (630 mg, 3.6 mmol, 92% yield). LC-MS (M-H) = 177.2

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Reference£º
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (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.100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.

A. 7-([1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluoro phenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester [1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hexane and 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester were reacted and purified according to the procedure of Example 23.A to provide the title product as a solid, mp 181-183 C. (72% yield). 1 H NMR (MeOH-d4): 8.57 (s, 1H), 7.96 (bd, J=12.4 Hz, 1H), 7.63 (m, 1H), 7.26 (m, 2H), 4.3 (vbm, 1H), 4.28 (q, J=7.0 Hz, 2H), 3.8 (vbm, 2H), 1.72 (m, 1H), 1.42 (s, 9H), 1.31 (t, J=7.0 Hz, 3H), 0.98 (m, 4H), 0.65 (m, 1H).

The synthetic route of 100491-29-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc; US5164402; (1992); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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. 7-([1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester [1alpha,2alpha,5alpha]-1-tert-Butoxycarbonylamino-2-methyl-3-azabicyclo[3.1.0]hexane and 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester were reacted and purified according to the procedure of Example 23.A to provide the title product as a solid, mp 181-183C (72% yield). 1H NMR (MeOH-d4): 8.57 (s, 1H), 7.96 (bd, J=12.4 Hz, 1H), 7.63 (m, 1H), 7.26 (m, 2H), 4.3 (vbm, 1H), 4.28 (q, J=7.0 Hz, 2H), 3.8 (vbm, 2H), 1.72 (m, 1H), 1.42 (s, 9H), 1.31 (t, J=7.0 Hz, 3H), 0.98 (m, 4H), 0.65 (m, 1H).

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Reference£º
Patent; PFIZER INC.; EP413455; (1991); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

5,7-Dichloro-1,8-naphthyridin-2-amine, cas is 131998-24-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

. 5,7-dichloro-l,8-naphthyridin-2- amine (compound 1.2, 1.007 g, 4.70 mmoi) was dissolved in TFA (40 mL), then cooled 0 C. Sodium nitrite (1.623 g, 23.5 mmol) was added portion-wise at 0 C with stirring. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (20 niL), stirred for 5 minutes then carefully brought to pH =7 with NaOH (2 M). The resulting precipitated solids were filtered, washed with water and dried under reduced pressure to give compound 1.3 (864 mg, 85%). m/z (ES+) 215 (M+H)~.

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Reference£º
Patent; 3-V BIOSCIENCES, INC.; WAGMAN, Allan S.; JOHNSON, Russell J.; CAI, Haiying; HU, Lily W.; (195 pag.)WO2017/31427; (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.100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.

Example 7 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid. A mixture of tetrahydrofuran (450 cm3), water (50 cm3), methanesulfonic acid (127 cm3) and ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (United Kingdom Patent Publication No. GB 2,191,776) was heated at reflux for 1 hour, and then cooled to 25 C. The resulting crystals were isolated, washed with tetrahydrofuran, and dried under vacuum to afford 41.3 g (89%) of the above-titled compound: m.p.=250 C.; (Found: C, 50.4; H, 1.7; Cl, 9.9; F, 16.0; N, 8.0. C15 H6 ClF3 N2 O3 requires C, 50.8; H, 1.7; Cl, 10.0; F, 16.1; N, 7.9%); 1 H NMR (300 MHz, d6 -DMSO) delta 13.9 (s, 1H), 9.09 (s, 1H), 8.77 (d, J=7.5 Hz, 1H), 7.86 (td, J=5.9 and 8.8 Hz, 1H), 7.66 (ddd, J=2.7, 9.0 and 11.8 Hz, 1H), 7.39 (tm, J=8.6 Hz, 1H), 7.39 (tm, J=8.6 Hz, 1H); numax (DRIFTS) cm-1 3130, 3060, 2947, 2885, 2821, 2723, 2637, 2594, 1734, 1641, 1623, 1579, 1544, 1516.

The synthetic route of 100491-29-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc.; US6114531; (2000); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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.

(1) A mixture of 310 mg of 1-cyclopropyl-6-fluoro-7- chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 745 mg of 5-acetamidomethylisoindoline, 0.56 ml of triethylamine, and 5 ml of anhydrous chloroform was heated at 60-70 C. for 0.5 hours while stirring. The resulting reaction mixture was diluted with 25 ml of chloroform. The mixture was washed with 5% acetic acid and brine in this order, dried over anhydrous sodium sulfate, and condensed. The residue was crystallized by the addition of ethylether. The crystals were collected by filtration and recrystallized from a mixed solvent of chloroform, methanol, and ethanol to obtain 260 mg of 7-(5- acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester.

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Reference£º
Patent; Wakunaga Seiyaku Kabushiki Kaisha; US5026856; (1991); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem