Category: 33311-29-4

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO2

c) 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylidene imidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide (example 53) [0196] HOBt (84 mg; 0.55 mmol; 1.5 eq), DIPEA (323 muL; 1.85 mmol; 5 eq) and 4-(2-methoxyethoxy)aniline (81 mg; 0.48 mmol; 1.3 eq) were added to a solution of 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (150 mg; 0.37 mmol; 1 eq) in dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 2 days. Ethyl acetate (10 mL) and water (5 mL) were added and the layers were separated. The organic layer was washed with saturated ammonium chloride (10 mL), water (10 mL) and sodium chloride (2 x 15 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was triturated in ethyl acetate, washed with petroleum ether, and concentrated to dryness. The residue was taken up in ethyl acetate/cyclohexane (200 muL) until precipitation, filtration. The title compound, 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide, was obtained in 25 % yield (50 mg) as a yellow solid. 1H-NMR (Acetone-d6): delta (ppm) 2.85 (m, 1H), 3.17 (m, 2H), 3.36 (s, 3H), 3.40 (m, 1H), 3.65 (m, 2H), 3.68 (s, 3H), 3.70 (m, 1H), 4.09 (m, 2H), 4.31 (m, 1H), 4.63 (m, 1H), 6.87 (m, 4H), 7.25 (m, 4H), 7.49 (m, 4H), 9.34 (s, 1H); MS (ESI+): m/z = 551.9 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33311-29-4.

Reference:
Patent; Vivalis; Guedat, Philippe; Berecibar, Amaya; Ciapetti, Paola; Venkata Pithani ,Subhash; Trouche, Nathalie; EP2664616; (2013); A1;,
Ether – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 33311-29-4

In a 100 mL 3-neck RBF, N-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amine (0.205 g), 4-(2-methoxyethoxy)aniline (0.137 g), Cs2CO3 (0.266 g) and Xantphos (0.032 g) were taken in degassed 1,4-dioxane (8.0 mL) and reaction mixture was degassed under argon for 30 minutes. Palladium acetate (0.013 g) was added to reaction mixture and again it was degassed for 30 minutes. The reaction mixture was heated to 80 C. and stirred for 3.5 h. The reaction was monitored on TLC using hexane:ethyl acetate: (5:5) as mobile phase. After completion, the reaction mixture was allowed to cool at room temperature. The reaction mixture was poured into water and product was extracted with ethyl acetate (3*25 mL). The ethyl acetate layer washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure. Crude material was purified by triturating with diethyl ether to give 0.1 g of N4-(2-(benzyloxy)-5-nitrophenyl)-5-fluoro-N2-(4-(2-methoxyethoxyl)phenyl)pyrimidine-2,4-diamine. 1H NMR: CDCl3 (400 MHz): 3.47 (d, 3H, J=11.6), 3.77 (dd, 2H, J=4.8, 8.8), 4.15 (t, 2H, J=4.8), 5.28 (s, 2H), 6.96 (d, 1H, J=8.8), 7.03 (d, 1H, J=8.8), 7.08 (d, 1H, J=9.2), 7.45 (m, 7H), 7.83 (s, 1H), 7.9 (d, 2H, J=2.8), 8.02 (dd, 1H, J=2.1, 6.8), 9.18 (s, 1H).

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

33311-29-4, name is 4-(2-Methoxyethoxy)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C9H13NO2

b. 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid [4-(2-methoxy-ethoxy)-phenyl]-amide; A mixture of 4-(6,7-dimethoxy-quinazolin-4-yl)-piperidine-1-carbonyl chloride (18 mg, 0.0536 mmol), as prepared in Example 3a, 4-(2-methoxy-ethoxy)-phenylamine (8.9 mg, 0.0533 mmol), as prepared in the previous step, and triethylamine (14 muL, 0.1 mmol) was stirred in DMSO (0.5 mL) at 50 C. overnight. The reaction was then cooled to RT, partitioned between EtOAc (10 mL) and H2O (10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by prep tlc (1:9 MeOH/DCM) afforded the title compound as a brown solid (5.7 mg, 23%). 1H NMR (300 MHz, CDCl3) delta 9.16 (s, 1H), 7.28-7.25 (m, 4H), 6.89 (m, 2H), 6.33 (br s, NH), 4.29-4.24 (m, 2H), 4.12-4.07 (m, 8H), 3.74 (m, 2H), 3.59 (m, 1H), 3.45 (s, 3H), 3.17 (m, 2H), 2.22-2.08 (m, 2H), 2.05-1.97 (m, 2H); LC/MS (ESI): calcd mass 466.2, found 467.4 [M+1]+.

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baindur, Nand; Gaul, Michael David; Kreutter, Kevin Douglas; Baumann, Christian Andrew; Kim, Alexander J.; Xu, Guozhang; Tuman, Robert W.; Johnson, Dana L.; US2006/281772; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 33311-29-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (492 mg, 2.95 mmol) and 4-(2-methoxy-ethoxy)-phenylamine (492 mg, 2.95 mmol) in CH2Cl2 (12 mL) and glacial AcOH (14 drops) was added NaBH(OAc)3 (758 mg, 3.58 mmol) and the reaction stirred at room temperature overnight. Purification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 96:4) gave the desired aniline (R)-3-{4-[4-(2-methoxy-ethoxy)-phenylamino-piperidin-1-yl}-butyronitrile (0.72 g, 94%) as an orange oil.

The chemical industry reduces the impact on the environment during synthesis 4-(2-Methoxyethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AnorMED Inc.; US2005/277668; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 33311-29-4,Some common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[00511] To a solution of tert-butyl 3-(2-chloro-5-nitropyrimidin-4-ylamino )phenylcarbamate(1) (430 mg, 1.37 mmol) in THF (10 mL) was added DIEA (530 mg, 4.1 mmol) and 4-(2-methoxyethoxy)aniline (39) (274 mg, 1.64 mmol) at r.t. under N2 atmosphere. The resultingmixture was stirred at r.t. overnight. The solvent was removed and the residue was purified byflash column chromatography (silica gel, 0 to 5% ethyl acetate in PE/DCM (1/1), with 0.5%TEA) to provide tert-butyl 3-(2-( 4-(2-methoxyethoxy)phenylamino )-5-nitropyrimidin-4-ylamino)phenylcarbamate (2) (559 mg, 96%) as a yellow solid. LC-MS (ESI) m/z (M+1) 497.1.

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; YAN, Shunqi; LOURY, David, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; WANG, Longcheng; WO2014/130693; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 33311-29-4, A common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

tert-Butyl (3-((2-chloro-5-fluoropyrimidin-4-yl)amino)phenyl)carbamate (800 mg, 2.37 mmoL) and 4-(2-methoxyethoxy)aniline (576 mg, 2.84 mmoL) were suspended in tert-amyl alcohol (14 mL) and acetic acid (5 drops). Heated to reflux for 4 h. After cooling, solvent was removed via rotary evaporation. The dark oil was partitioned between water/brine and THF (10 mL each), agitated, and separated layers and dried organic phase over sodium sulfate. The solvent was removed via rotary evaporation to afford a purple solid, 0.55 g. LC/MS (RT=2.997/(M+1)) 470.2. Additional 150 mg of product minus the (BOC) protecting group crystallized from the aqueous layer

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 33311-29-4, A common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of compound 27-1 in DMF (50 mL) was added dropwise DIPEA (4.55 g, 35.23 mmol) and compound 27-1-1 (5 g, 30.2 mmol) under nitrogen atmosphere at 0 C., and the reaction solution was reacted at 0 C. for 0.5 h, followed by warmed to r.t. and reacted for another 1 h. The resulting reaction solution was diluted with EtOAc (50 mL) and washed with brine (30 mL×3). The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to give a residue was purified by column chromatography (3% to 8% of PE/EtOAc) to afford the title compound (360 mg, 26.3%) as white solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(2-Methoxyethoxy)aniline

To a solution of 2.4-dichloro-l,3,5-triazine A.91 (2 g, 13.34 mmol) in DMF (10 mL) at 0 0C were added DIEA (2.4 mL, 13.77 mmol) and 4-(2-methoxyethoxy)benzenamine (2.027 g, 12.12 mmol) and the mixture was stirred at 0 0C for 30 minutes and then room temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (50 mL x 1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The brown solid was purified by silica gel column chromatography using 30% of ethyl acetate in hexane as eluent to give 4-chloro-N-(4-(2-methoxyethoxy)phenyl)-l,3,5-triazin-2-amine A.92 (2.887 g, 84.8% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 10.58 (1 H, s), 8.56 (1 H, d, J=5.9 Hz), 7.51 (2 H, t, J=9.5 Hz), 6.96 (2 H, t, J=7.9 Hz), 4.04 – 4.1 1 (2 H, m), 3.65 (2 H, dd, J=5.3, 3.8 Hz), 3.31 (3 H, s); Mass Spectrum (ESI) m/e = 281.0 [M+l].

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 4-(2-Methoxyethoxy)aniline

To a solution of compound 3 (400 mg, 1.0 mmol) and 4-(2-methoxyethoxy)aniline (0.2 g, 1.2 mmol) in 8 ml dioxane was added 4-methylbenzenesulfonic acid monohydrate (0.15g, 0.8 mmol). The mixture was stirred at 100 0C for two hours. The solvent was evaporated. The residue was dissolved in 30 ml ethyl acetate and washed with NaHCO3 aqueous solution, water and brine. The organic layer was separated and dried over Na2SO4. After removal of solvent, the crude product was subject to chromatography on silica gel (hexane:EtOAc = 1 :1). 0.40 g of the title compound 5 was obtained: MS m/z: 530.1, 532.1(M+H+).

The synthetic route of 4-(2-Methoxyethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVILA THERAPEUTICS AND USES THEREOF; WO2009/158571; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(2-Methoxyethoxy)aniline

In a 25 mL three neck RBF with thermometer pocket, a solution of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate (0.250 g) in 1,4-dioxane (8.0 mL) was added. 4-(2-Methoxyethoxy)aniline (0.122 g) was added and the reaction was degassed for 10 minutes under argon. After 10 minutes, Xantphose (0.0176 g) and Cs2CO3 (0.396 g) were added and again degassed the reaction for 10 minutes followed by addition of Pd (OAc)2 (0.003 g) under argon. The reaction was heated to 80 C. and stirred for 3.5 hr under argon. The reaction was monitored on TLC using hexane:ethyl acetate (2:8) as mobile phase. After completion of the reaction, the reaction mixture was allowed to cool at room temperature. The reaction mixture was poured into water and product was extracted with ethyl acetate (3*25 ml). Ethyl acetate layer washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to give 0.250 g of tert-butyl (5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate. This crude material was used in the next step without any further purification. M+1=539.9.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem