Category: 5961-59-1

5961-59-1, name is 4-Methoxy-N-methylaniline, 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. Computed Properties of C8H11NO

An activated carbon supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 mol%) was added to a 10 mL Schlenk tube,After evacuation of argon, add 1 mL of solvent (toluene).Under argon protection, to the above system,Separately, phenylsilane (78.9 mg, 0.75 mmol) was added successively,III-3 (R2 = p-methoxyphenyl, R3 = methyl) (41.2 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol).The reaction was carried out at 80 C with stirring for 15 hours.After completion of the reaction, 3 mL of ethyl acetate was added to the system,The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated,Dried over anhydrous Na2SO4, filtered,The solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 100 mixed solvent,The product was isolated and purified to give the target product IV-333.6 mg in 74% yield.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Engineering College; Zhu Lei; Wang Liansheng; Li Bojie; Li Wei; Fu Boqiao; (21 pag.)CN106892826; (2017); A;,
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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5961-59-1

HATU (1.52 g, 4.01 mmol) was added to a stirred solution of 4-methoxy-N-methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.01 mmol) iln DMF (20 mL) and DIPEA (1.27 mL, 7.29 mmol) and the reaction mixture was stirred at rt for 4 h. The reaction mixture was concentrated and the crude oil was then partitioned between EtOAc (-60 mL) and 1/2 sat. NaHCCb (aq.) (-60 mL). The organic component was washed with brine (-40 mL), dried (MgS04), filtered and concentrated. The residual oil was then purified using a Biotage Horizon (80g SiC , 10- 40% EtOAc/hexanes) to yield Intermediate 1 (1.34 g) as clear amber viscous oil. LC-MS retention time = 3.17 min; m/z = 285.3 [M+H-Boc]+. (Column: Phenomenex Luna C18 2.0 X 50 mm 3 muiotaeta. Solvent A = 95% Water : 5% Acetonitrile : 10 mM NH4OAc. Solvent B = 5% Water : 95% Acetonitrile : 10 mM NH4OAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 4 minutes, then a 1 -minute hold at 100% B. Wavelength = 220 nm). NMR (400 MHZ, CDCb) delta ppm 7.25 – 7.20 (m, 3H), 7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (app q, J=7.4 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s, 9H).

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5961-59-1

Example 1: Key Intermediate (S)-N-(1-(4-methoxyphenyl)(methyl)amino)-1-carbonyl-3-phenyl-2-yl)propynamide (4 Preparation of The starting material Boc-L-phenylalanine (1) (8.75 mmol, 2.3 g) was added to 15 mL of anhydrous dichloromethane solution. To this solution was then added 1H-benzotriazol-1-yloxytripyrrolidinylhexafluorophosphate (10.9 mmol, 5.7 g). After stirring for 0.5 h under ice bath, N,N-diisopropylethylamine (21.87 mmol, 3.61 mL) and N-methyl-4-aminoanisole (7.29 mmol, 1.0 g) were added to remove the ice bath. Stir at room temperature for 12 h. After the reaction is completed, the solvent is distilled off under reduced pressure, then saturated sodium bicarbonate solution is added to the bottle residue, and ethyl acetate is extracted; the organic layer is separated, 1N HCl solution is added, and ethyl acetate is extracted; the organic layers are combined and saturated. The brine was washed and the organic phase was dried over anhydrous sodium sulfate; Filtration and evaporation of the solvent under reduced pressure gave the intermediate compound tert-butyl-(S)-(1-((4-methoxyphenyl)(methyl)amino)-1-oxo-3-phenylpropyl- 2-Carboxylic acid (2) Crude 2.63 g, yellow oil, 94% yield,

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; Shandong University; Zhan Peng; Wu Gaoshan; Liu Xinyong; Li Guoxiong; Kang Dongwei; Yu Ji; Sun Lin; (25 pag.)CN108033952; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 5961-59-1,Some common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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.

The synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-N-methylaniline, its application will become more common.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (91 pag.)WO2016/22890; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5961-59-1, A common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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.

A solution of 62 (tert-butoxycarbonyl)-l-phenylalanine (1, 8.75mmol, 2.3g) in 15mL 63 dichloromethane was added PyBop (10.9mmol, 5.7g) at 0C, and the mixture stirred for 0.5h. Subsequently, 64 DIEA (21.87mmol, 3.61mL) and 25 4-methoxy-N-methylaniline (7.29mmol, 1.0g) were added to the mixture and then stirred at room temperature for another 8-9h (monitored by TLC). The resulting mixture was evaporated under reduced pressure and the residue was initially washed by 1N HCl and extracted with ethyl acetate (3×20mL). Then, the combined organic layer was washed with saturated sodium bicarbonate (3×50mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford corresponding crude intermediate 65 2 as yellow oil with a yield of 94%. 1H NMR (400MHz, DMSO-d6) delta 7.21 (d, J=8.4Hz, 3H), 7.15 (d, J=7.1Hz, 2H), 7.02 (d, J=8.4Hz, 2H), 6.85-6.75 (m, 2H), 4.15 (q, J=5.4Hz, 1H), 3.80 (s, 3H), 3.12 (s, 3H), 2.81-2.54 (m, 2H), 1.30 (s, 9H). 13C NMR (100MHz, DMSO) delta 172.21, 158.98, 155.74, 138.53, 136.13, 129.28, 128.47, 126.70, 115.21, 78.33, 55.94, 53.53, 37.86, 37.10, 28.65. ESI-MS: m/z 385.4 (M+1)+, C22H28N2O4 (384.2)

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Gaochan; Zalloum, Waleed A.; Meuser, Megan E.; Jing, Lanlan; Kang, Dongwei; Chen, Chin-Ho; Tian, Ye; Zhang, Fangfang; Cocklin, Simon; Lee, Kuo-Hsiung; Liu, Xinyong; Zhan, Peng; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 478 – 492;,
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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H11NO

General procedure: Compound 1a (0.0016g, 0.0043 mmol),HBpin (94L, 0.645 mmol), N-methylaniline (23 L, 0.215mmol), the internal standard1,3,5-trimethoxybenzene (10 mg) and CD3CN (0.4 mL) were loaded in a dried J-Young Tube under argonatmosphere. The sample was degassed using a freeze-pump-thaw method, and CO2 (approximately 45 mg)was introduced into the NMR tube at -196 oC. The reaction was monitored by NMR spectroscopy.PhMeN(CHO) 8a was purified by preparative TLC using ethyl acetate/hexane/triethylamine as eluent.Spectral data of all products are in accordance with those reported in the literature.

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:
Article; Wu, Di; Wang, Ruixing; Li, Yongxin; Ganguly, Rakesh; Hirao, Hajime; Kinjo, Rei; Chem; vol. 3; 1; (2017); p. 134 – 151;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5961-59-1, name is 4-Methoxy-N-methylaniline, 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. Application In Synthesis of 4-Methoxy-N-methylaniline

An activated carbon supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 mol%) was added to a 10 mL Schlenk tube,After evacuation of argon, add 1 mL of solvent (toluene).Under argon protection, to the above system,Separately, phenylsilane (78.9 mg, 0.75 mmol) was added successively,III-3 (R2 = p-methoxyphenyl, R3 = methyl) (41.2 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol).The reaction was carried out at 80 C with stirring for 15 hours.After completion of the reaction, 3 mL of ethyl acetate was added to the system,The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated,Dried over anhydrous Na2SO4, filtered,The solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 100 mixed solvent,The product was isolated and purified to give the target product IV-333.6 mg in 74% yield.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Engineering College; Zhu Lei; Wang Liansheng; Li Bojie; Li Wei; Fu Boqiao; (21 pag.)CN106892826; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 5961-59-1, name is 4-Methoxy-N-methylaniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5961-59-1, Recommanded Product: 5961-59-1

[[00146]] To a mixture of N-methyl-p-anisidine (2.8 g, 20 mmol) and malonic acid (4.3 g, 40 mmol) was added POC13 (17 mL). After heating at [90¡ã] C for 1.5 hr, the reaction mixture was poured over ice and basified with 6N [NAOH] to a pH of 14. The solution was then filtered and the filtrate was acidified with, 6N HC1 to pH 3. The precipitate was filtered and dried to afford a brown solid (1.8 g, [50percent). H] NMR (300 MHz, [MEOD-] d4) [8] 3.65 (3H, s), 3.86 (3H, s), 5.97 [(1H,] s), 7.28 [(1H,] dd, J [=] 2.8, 9.3 Hz), 7.49 (2H, d, J = 9.3 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-N-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2003/106452; (2003); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 5961-59-1, These common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, 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.

HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N- methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at RT for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (60 mL) and 1/2 sat. NaHCO3 (aq) (60 mL). The organic component was washed with brine (40 mL), dried (Mg504), filtered, concentrated and purified using a Biotage Horizon (80g5i02, 10-40% EtOAc/hexanes) to yield (5)-tert-butyl (1-((4- methoxyphenyl)(methyl)amino)- 1 -oxo-3 -phenylpropan-2-yl)carbamate (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 mm; mlz = 385.3 [M+H]. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 pm. Solvent A = 95% Water:5% Acetonitrile:10 miVi NH4OAc. Solvent B = 5% Water:95% Acetonitrile:10 miViNH4QAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time= 4 mm. Wavelength = 220). ?H NMR (400MHz, CDC13) oe 7.25 – 7.20 (m, 3H),7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (q, J=7.4 Hz, 1H), 3.83 (s, 3H),3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s,9H).

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PENDRI, Annapurna; LI, Guo; BENDER, John A.; YANG, Zhong; WANG, Alan Xiangdong; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; MEANWELL, Nicholas A.; GENTLES, Robert G.; WO2015/61518; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Methoxy-N-methylaniline

4-Acetyl-N-(4-methoxy-phenyI)-N-methyl-benzamide 152. To a stirred solution of 4-acetylbenzoic acid (0.164 g, 1 mmol) and N-methyl-j?-anisidine (0.165 g, 1.2 mmol) in dry DCM (5 mL) and NEt3 (0.17 mL) was added DMAP (catalytic) and the solution was cooled on ice. To this was then added EDCI (0.383 g, 2 mmol) and the reaction was allowed to warm to rt with stirring over 22 h. To this was added sat. aq. bicarb, and DCM and the organic layer was separated and concentrated under reduced pressure. Purification by flash chromatography using an elution gradient of hexane to 30percent EtOAc in hexane gave the title compound, 0.186 g5 66 percent: 1H NMR delta (400 MHz, CDCl3) 2.47 (3H5 s), 3.40 (3H, s), 3.66 (3H5 s), 6.67 (2H5 d, J= 8.6 Hz), 6.89 (2H, d, J= 8.2 Hz)5 7.31 (2H, d5 J= 7.8 Hz)5 7.69 (2H5 d5 J= 7.8 Hz); 13C NMR delta (100 MHz, CDCl3) 26.5, 38.2, 55.2, 114.3, 127.5, 127.9, 128.5, 136.9, 137.0, 140.4, 158.0, 169.5, 197.4; LC/MS (APCI) m/z 304.47 (M-H)-; HPLC tT = 3.61 min (>99percent) 90percent MeCN m H2O.

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 5961-59-1.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem