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, Example 37 (Method Cl); Synthesis of N-(4-(7-methoxy-l ,5-naphthyridin-4-yloxy)phenyl)-4-(4- methoxyphenyl)phthalazin-l-amineA 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-l- ylamino)phenol and 3 equivalents of cesium carbonate (342 mg, 1.048 mmol) in 1.8 mL of DMF. The mixture was stirred at RT for 10 min. Following addition of 8-chloro-3- methoxy-l,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150 0C for 15 min in the microwave, at which time the reaction was determined complete by LC/MS. The mixture was cooled to ambient temperature and diluted with water. The solids were filtered and washed with water. The solids were triturated with methanol, filtered to remove remaining impurities, washed with additional methanol and dried under vacuum to afford N-(4-(7-methoxy- 1 ,5-naphthyridin-4-yloxy)phenyl)-4-(4- methoxyphenyl)phthalazin-l -amine as a light orange solid. MS [M+H]=502; Calc’d 501.54 for C30H25N5O3.

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

Reference£º
Patent; AMGEN INC.; WO2008/124083; (2008); A2;,
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

Step 1: 8-Chloro-1,5-naphthyridin-3-ol A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (1200 mg, 6166 mumol), boron tribromide (6412 mul, 67825 mumol) and dichloroethane (10277 mul, 6166 mumol). The vessel was sealed and the mixture was stirred at 60 C. for 16 h. The reaction mixture was carefully diluted with DCM, and the solids were filtered. The crude material was purified by silica gel chromatography with 40-70% (90:10:1 DCM/MeOH/NH4OH)/DCM to afford 8-chloro-1,5-naphthyridin-3-ol. MS:[M+H]=181.

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
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The naphthyridine compound, name is 3-Bromo-1,5-naphthyridine,cas is 17965-71-8, mainly used in chemical industry, its synthesis route is as follows.

Preparation of 1 ,5-naphthyridin-3-amine:[0589] Commercial 3-bromo-[l,5]naphthyridine (1.00 g, 4.8 mmol) was dissolved in 50 mL dioxane. To it were added t-butyl carbamate (0.85 g, 7.2 mmol), cesium carbonate (3.13 g, 9.6 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol) and XantPhos (0.42g, 0.72 mmol). The mixture was degassed with Ar stream and stirred under Ar in 85C bath for 5 h. The mixture was concentrated, taken into 400 mL EtOAc and 200 mL water. The organic phase was separated, dried, concentrated and subjected to flash column (0-30% EtOAc in DCM) to obtain tert- butyl l,5-naphthyridin-3-ylcarbamate (1.04 g, 88% yield). This compound was treated with 50 mL 4N HCl in dioxane for overnight. To the suspension was poured diethyl ether 300 mL. The suspension was vigorously stirred. The solid product was collected by filtration as 1,5- naphthyridin-3 -amine di-HCl salt

17965-71-8, As the rapid development of chemical substances, we look forward to future research findings about 17965-71-8

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
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15936-10-4, 2-Chloro-1,8-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 2 Preparation of 2-(4-(1,8-naphthyridin-2-yloxy)phenoxy)propanoic acid STR9 A 3-necked flask was equipped with a thermometer, a magnetic stirrer, a reflux condenser and a nitrogen line and flushed with nitrogen. The flask was charged with 15 ml of hexane and 1.38 gm (28.8 m moles) of 50% NaH/oil dispersion. After stirring for 10 minutes the hexane was decanted and replaced with 5 ml of DMSO followed by the dropwise addition of a solution of 2.18 gm (12 m moles) of 2-(4-hydroxyphenoxy)propanoic acid in 5 ml of DMSO. The mixture was warmed to 60 C. and a solution of 1.97 gm of 2-chloro-1,8-naphthyridine in 10 ml of DMSO was added. After warming the reaction mixture at 95 C. for one hour, the mixture was cooled to room temperature and water cautiously added. The solution was extracted with methylene chloride and the aqueous phase neutralized with acetic acid to give a white precipitate. The aqueous mixture was extracted with CH2 Cl2 and the organic layer washed twice with water, dried over Na2 SO4 and evaporated to dryness to give 3.3 gm of yellow solid which could not be redissolved in ether or CH2 Cl2., 15936-10-4

As the paragraph descriping shows that 15936-10-4 is playing an increasingly important role.

Reference£º
Patent; The Dow Chemical Company; US4472193; (1984); A;,
1,8-Naphthyridine – Wikipedia
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1375301-90-8, 3-Bromo-1,7-naphthyridin-8(7H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1375301-90-8

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

As the paragraph descriping shows that 1375301-90-8 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

23616-31-1, 1,6-Naphthyridin-5(6H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,23616-31-1

[0622] A suspension of XI-3 (2.36 g, 15.7 mmol, 1 eq), N-bromosuccinimide (3.1 g, 17.3 mmol, 1 eq), and 50 mL of 1,2-dichloroethane was stirred at rt for 3.5 hrs. The mixture was filtered; the solids were washed successively with small amounts of chloroform, water, and diethyl ether, and then dried to leave XI-4 (0.8 g, 23percent yield). MS (ESI) m/z (M+H)+ 226.8.

23616-31-1 1,6-Naphthyridin-5(6H)-one 5520368, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The naphthyridine compound, cas is 952059-69-7 name is 8-Chloro-3-methoxy-1,5-naphthyridine, mainly used in chemical industry, its synthesis route is as follows.

952059-69-7, Step 1: 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine To a resealable pressure vessel was added n-methyl-4-nitroaniline (0.911 ml, 7.19 mmol), pyridinium p-toluenesulfonate (1.81 g, 7.19 mmol), 8-chloro-3-methoxy-1,5-naphthyridine (1.000 g, 5.14 mmol), and n-BuOH (15 mL). The vessel was sealed and heated to 100 C. After 4 h, the mixture was cooled to RT, diluted with 1 N NaOH, and extracted with EtOAc. The organic fraction was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography using 50-100% Hexanes:EtOAc to afford 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine as a yellow solid. MH+=311.21.51 min.

As the rapid development of chemical substances, we look forward to future research findings about 952059-69-7

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

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, To a solution OF 4- [ (4-BROMOPHENYL) (ethoxyimino) methyl]-1-(4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), 1, 8-naphthyridine-2-carboxylic acid (25 mg, 0.14 MMOL), and Et3N (44 mg, 0.43 MMOL) in DMF (3 mL, anhydrous) was added HATU (60 mg, 0.16 MMOL) at room temperature. After 16 h the reaction mixture was poured into ice water, and the solid was collected by filtration. The solid was dissolved in CH2CI2 and dried over NA2S04. Concentration in vacuo, and purification by preparative TLC (CH2CI2-MEOH, 9: 1) afforded the title compound as a light brown powder. MS: 564 (M+).

215523-34-5 1,8-Naphthyridine-2-carboxylic acid 735156, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The naphthyridine compound, cas is 15944-34-0 name is 7-Chloro-1,8-naphthyridin-2-ol, mainly used in chemical industry, its synthesis route is as follows.

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 NaOMe (25 wt% in MeOH, 161 rnL). The resulting solution was stirred at reflux for 15 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).

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

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/116337; (2010); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

The naphthyridine compound, cas is 72754-05-3 name is 6-Bromo-1,8-naphthyridin-2-ol, mainly used in chemical industry, its synthesis route is as follows.

72754-05-3, c) (EVtert-butyl 3-(7-oxo-7.8-dihvdro-l ,,8-naphtfayridin-3-yr)acrylate; A reaction vessel was charged with 6-bromo-l,8-naphthyridin-2(lH)-one (1.5g, 6.69 mmol), tert-bxyl acrylate (4.86 mL, 33.45 mmol), and (J-Pr)2EtN (3.5 niL, 20.07 mmol) followed by DMF (40 mL). The solution was de-oxygenated with argon for 20 min. The mixture was treated with Pd(OAc)2 (150 mg, 0.67 mmol) and P(o-tol)3 (407 mg, 1.34 mmol) then heated to 100 0C for 15 h (overnight). A TLC anlaysis indicated that only the starting arylhalide is present. At this time the mixture was a yellow suspension. To this mixture was added 20 DMSO (20 mL) and an additional 75 mg OfPd(OAc)2. The mixture was heated at 100 0C for 24 h. After cooling, the dark mixture was filtered through celite and the filter cake was rinsed with EtOAc (100 mL). The filtrate was extracted with EtOAc (2 x 100 mL). The combined organic fractions were washed with brine (2 x 100 mL), H2O (100 mL), dried over MgSO4 and filtered through a pad of silica gel. The filtrate was concentrated to about 50 mL then treated with about 150 mL hexanes to form a precipitate. The precipitate was filtered to give the product as a light brown solid. Yield: 700 mg(39%); 1H-NMR (300 MHz, DMSO-d6) delta 12.36 (s, IH), 8.83 (d, IH, J = 2.3 Hz), 8.53 (d, IH, J = 2.3 Hz), 7.89 (d, IH, J = 9.0 Hz), 7.64 (d, IH, J = 18.0 Hz), 6.65 (d, IH, J = 18.0 Hz), 6.62 (m, IH)5 1.51 (s, 9H); ESIMS m/z 273 [Ci5H16N2O3 + H]+

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

Reference£º
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem