Tag: M.W:100-200

Name is 8-Chloro-3-methoxy-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

10g and 11.1gThe 1,5-naphthyridine derivative is dissolved in DMF.2.51 g of sodium hydride was added in portions on an ice bath.Add 5 minutes at room temperature after adding,After stirring for 2 hours at 50C,TLC showed that the raw material spots almost disappeared.Cool the reaction solution to ice bathIn an ice bath,Add 2.51g of sodium hydride,After stirring for 5 minutes,Add 4.5 ml acetyl chloride,There are a lot of white solids in the solution,After stirring for 3h at room temperature,Add 200ml of water to quench unreacted sodium hydride,Add 400ml of ethyl acetate to extractThe organic layer is washed three times,100ml each time.The organic layer is dry,concentrate,The concentrated oil was dissolved in 200 ml of THF.Join 37g TBAF,Stir at room temperature,The reaction gradually turned black.Stop the reaction after 30 minutes,Diluted the reaction with 100 ml of ethyl acetateWash 3 times,30ml each time.After the ethyl acetate layer is dry,concentrate,Get crude product.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO251,mainly used in chemical industry, its synthesis route is as follows.,55716-28-4

B. 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0 C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3*500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101 C.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Methoxy-1,7-naphthyridin-6-amine,belong naphthyridine compound

Reference£º
Patent; Novartis AG; US6136821; (2000); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Chloro-1,5-naphthyridine, and cas is 7689-62-5, its synthesis route is as follows.,7689-62-5

0001-3 A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was added dropwise to a mixture of 2-chloro-1,5-naphthyridine (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) at 85 C., and acetic acid (2 mL) was added thereto, followed by stirring at 85 C. for 3 hours. The reaction mixture was cooled to room temperature, and added dropwise to a 6 mol/L sodium hydroxide aqueous solution (60 mL) under ice-cooling. The solid matter was collected by filtration, suspended in methanol (5 mL), and subjected to an ultrasonic treatment. The solid matter was collected by filtration, and washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v % methanol aqueous solution (8 mL), the resultant product was subjected to an ultrasonic treatment, and the solid matter was collected by filtration, thereby obtaining 7-bromo-2-chloro-1,5-naphthyridine (3.33 g) as a pale yellow solid. MS m/z (M+H): 243.

7689-62-5 is used more and more widely, we look forward to future research findings about 2-Chloro-1,5-naphthyridine

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

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

In the second step, 2-methyl-1,8-naphthyridine (27 mmol, 3.8 g) was dissolved in diethyl ether (50 mL) under a nitrogen atmosphere, and then cooled to -78¡ã C., and added dropwise with stirring (0.5 h increments). (b) Diethyl ether solution (20mL) of CH3-Li (32mmol, 1.6M, purchased from JV of BAHL Technology, Inc.), and then warmed to room temperature (25¡ãC) and stirred for 12h. The reaction was quenched by adding 15mL of saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with chloroform three times. The organic layers were combined and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give an orange-red oil. KMnO4 (96 mmol, 15.2 g, purchased from Beijing Chemical Industry Plant) was added at room temperature. After stirring for 6 h at 25¡ã C., the mixture was suction filtered, and the filtrate was evaporated under reduced pressure to obtain a crude solid product, which was further purified by column chromatography (petroleum ether/ethyl acetate mixture with a volume ratio of 100/1). A compound (known compound) having the structure represented by the formula (1-1) is obtained,The yield was 75percent.

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; Chinese Academy Of Sciences Chemical Institute; Fan Qinghua; Ma Wenpeng; Chen Fei; He Yanmei; (51 pag.)CN105111208; (2018); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,8-Diazanaphthalene, cas is 254-60-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A. A solution of [1,8]naphthyridine (0.2 mmol) and potassium amide (0.8 mmol) in liquid ammonia (20 mL) is stirred at -40 C. for 3 h. The solution is concentrated. Residue is partitioned between EtOAc and water. EtOAc layer is separated and washed successively with water and brine. EtOAc layer is dried over sodium sulfate, filtered and concentrated to give [1,8]naphthyridin-2-ylamine which is used as is for the next step., 254-60-4

With the rapid development of chemical substances, we look forward to future research findings about 1,8-Diazanaphthalene

Reference£º
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

Step 1: N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide In a screw cap test tube were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (281 mg, 1443 mumol), N-(5-aminopyrimidin-2-yl)benzamide (281 mg, 1312 mumol) and pyridinium p-toluenesulfonate (494 mg, 1968 mumol) in butan-2-ol (2623 mul, 1312 mumol) then heated at 100 C. The reaction turned black in a minute. After 1 h, the reaction mixture showed full conversion to product according to LCMS. The reaction mixture was diluted with CH2Cl2, neutralized with sat. NaHCO3. An emulsion was formed but the two layers eventually separated. The aqueous phase was extracted 3 times with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated under reduce pressure to give a tan solid. The solid was triturated with hexane, filtered, and dried under vacuo. Brown solid was collected. LCMS confirmed the presence of the product, N-(5-(7-methoxy-1,5-naphthyridin-4-ylamino)pyrimidin-2-yl)benzamide. MS Calcd for C20H16N6O2: [M]+=372. Found: [M+H]+=373.

With the complex challenges of chemical substances, we look forward to future research findings about 952059-69-7,belong naphthyridine compound

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

Name is 8-Chloro-3-methoxy-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 952059-69-7, its synthesis 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).

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO139,mainly used in chemical industry, its synthesis route is as follows.,337958-60-8

Intermediate 8: 1,1-Dimethylethyl (3R)-3-{[(7-chloro-1,6-naphthyridin-5-yl)amino]methyl}-3-fluoro-1-piperidinecarboxylate[0387]5,7-dichloro-1,6-naphthyridine (5.01 g, 25.2 mmol) and 1,1-dimethylethyl (3R)-3-(aminomethyl)-3-fluoro-1-piperidinecarboxylate (5.32 g, 22.90 mmol) in NMP (20 ml) was added DIPEA (8.00 ml, 45.8 mmol) and the mixture was stirred at 100 C. for 72 h under nitrogen. The reaction was cooled and partitioned between ethyl acetate and water (200 ml each). The aqueous was washed with ethyl acetate. The combined organics were washed with water and the solvent was removed. The residue was dissolved in DCM and loaded onto a 100 g silica SNAP column and purified on the SP4 eluting with 0-50% ethyl acetate in cyclohexane over 17 CVs. Appropriate fractions were combined and the solvent was removed to give the title compound as a pale orange solid which was dried under high vacuum for 2 h (7.61 g).[0389]LCMS (Method B): Rt=1.12 min, MH+ 395/397

With the complex challenges of chemical substances, we look forward to future research findings about 5,7-Dichloro-1,6-naphthyridine,belong naphthyridine compound

Reference£º
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis 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.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

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

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.,1569-16-0

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).

1569-16-0 is used more and more widely, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

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