Tag: M.W=100-200

Application of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Synthesis of2-chloro-5-methoxy-N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine [0342] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 28.08 mmol) in tertiary butyl alcohol (35 mL) under argon atmosphere were added 2-(trifluoromethoxy) aniline (4 g, 22.47 mmol) and diisopropylethylamine (35 mL) at RT. The reaction mixture was stirred at 160 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 10% EtOAc:hexanes to afford 2-chloro-5-methoxy- N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine (2 g, 22%) as a colorless syrup. 1H-NMR (CDCls, 400 MHz): delta 8.64 (d, 1H), 7.79 (s, 1H), 7.72 (br s, 1H), 7.38 (t, 1H), 7.30-7.27 (m, 1H), 7.10-7.07 (m, 1H), 4.00 (s, 3H); LC-MS: 320.3 (M+l); (column; X Select CSH C-18 (50 x 3.0 mm, 3.5 muiotaeta); RT 4.63 min. 0.05% Aq TFA: ACN; 0.80 ml/min); TLC: 15% EtOAc:hexanes {Rf. 0.3).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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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;,
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Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

Example 85; Preparation of 8-iodo-2,7-dimethyl-N-(3-(trifluoromethoxy) phenyl)quinazolin-4- amiue4-Chloro-8-iodo-2,7-dimethylquinazoline (0.30 g, 0.94 mmol) and 3- (trifluoromethoxy)benzenamine (0.20 g, 1.1 mmol) were placed in a microwave vial containing 3 mL of IPA. The vial was capped and heated in a microwave reactor at 170 0C for 10 min. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate and washed (2x) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was dried with sodium sulfate, concentrated and purified by column chromatography on silica gel using a gradient of 20 to 60 percent EtOAc in hexanes to give a 8-iodo-2,7-dimethyl-N-(3- (trifluoromethoxy)phenyl)quinazolin-4-amine (0.32 g, 74percent) as an off-white solid. MS (M+H)+ 460.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2007/76092; (2007); A2;,
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Synthetic Route of 91-16-7, 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. 91-16-7, name is 1,2-Dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

The cooled solution of veratrol (32 ml) and acetic acid (125 ml) was slowly added to a cooled solution of methanol (20 ml) and acetaldehyde (21 ml). The mixed solution was thoroughly stirred for 1 hour, then concentrated sulthric acid (95%, 125 ml) was added over 2 hours and reacted with stirring for 20 hours. Afier the reaction was completed, the reaction mixture was poured into ice water to terminate the reaction. The reaction mixture was filtered, washed with water and subjected to colunm chromatography using chloroform as a developing solution to obtain isolated 2,3,6,7-tetrakis(methoxy)-9, 1 0-dimethylanthracene (1)

The chemical industry reduces the impact on the environment during synthesis 1,2-Dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY; SUH, Donghack; CHOI, Kyounghwan; (106 pag.)US2019/31586; (2019); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2734-70-5, name is 2,6-Dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 2734-70-5

To a solution of pentanenitrile (310 mg, 3.7 mmol) and 2-methoxy-6-methylaniline (518 mg, 3.40 mmol) in toluene (13 mL) at RT was added a solution of trimethylaluminum in toluene (1.7 mL, 3.4 mmol) at 0° C. The reaction mixture was heated at 110° C. for 1 h. The cooled reaction mixture was quenched with saturated solution of Rochelle’s salt (5 mL) and stirred at RT for 30 min. The reaction mixture was extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 20-100percent EtOAc/hexanes with 0.5percent Et3N to give Compound 1a (450 mg, 56percent) as a brown oil. LCMS (Method D) retention time=0.65 min, m/z=237.1 (M+H). 1H NMR (500 MHz, chloroform-d) delta 6.88 (t, J=8.4 Hz, 1H), 6.51 (d, J=8.3 Hz, 2H), 4.68-3.89 (m, 2H), 3.71 (s, 6H), 2.33 (br. s., 2H), 1.84-1.52 (m, 2H), 1.49-1.24 (m, 2H), 0.89 (br. s., 3H).

The synthetic route of 2734-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); A1;,
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Reference of 2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, This compound has unique chemical properties. The synthetic route is as follows.

1-Hydroxypyrene-2-carbaldehyde 3 (100 mg, 0.41 mmol) wasdissolved in CH2Cl2 and 2,2′-oxybis (ethylamine) (0.02 mL,0.20 mmol) was added to the reaction mixture. The reactionmixture was stirred at RT for 12 h. The precipitate formed wasfiltered and washed with cold CH2Cl2 to give 2 as a yellow solid(176 mg, 76.6%). m.p. 200 C. 1H NMR (CDCl3, 250 MHz): delta 14.53(s, OH), 8.61 (s, 2H), 8.32 (d, J 9.10 Hz, 2H), 7.99-7.80 (m, 8H), 7.54(s, 2H), 7.35 (d, J 8.98 Hz, 2H), 3.91 (s, 8H). 13C NMR (CDCl3,62.5 MHz): delta 167.16, 156.66, 132.52, 132.18, 127.00, 127.12, 126.88,126.81, 126.66, 125.97, 124.77, 124.20, 123.90, 122.96, 121.49, 119.52,115.34, 69.91, 58.44, 30.92. HRMS (FAB) calcd for C38H29N2O3[M + H]+ 561.2100; found 561.2178.

The chemical industry reduces the impact on the environment during synthesis 2,2′-Oxydiethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hu, Ying; Liu, Yifan; Kim, Gyoungmi; Jun, Eun Jin; Swamy; Kim, Youngmee; Kim, Sung-Jin; Yoon, Juyoung; Dyes and Pigments; vol. 113; (2015); p. 372 – 377;,
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Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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. HPLC of Formula: C9H13NO

The solution of 4-oxo-4-(pyridin-2-yl)butanal (326 mg, 2 mmol) in dichloromethane (15 mL) was added NaBH(OAc)3(1.27 g, 6 mmol) and HOAc (20 mg, 0.33 mmol) at -70C. The resulting suspension was stirred at the same temperature for 30 min. The reaction was warmed to 0C and added (5)-l-(4- methoxyphenyl)ethanamine (332 mg, 2.2 mmol). The resulting suspension was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1/10) to give the desired product (400 mg, 71 %) as a red solid. H NMR (400 MHz, CDC13) delta 8.42 (s, 1H), 7.58- 7.45 (m, 1H), 7.35 (d, / = 7.2 Hz, 1H), 7.15 (d, / = 7.6 Hz, 2H), 7.02 (s, 1H), 6.68 (d, / = 8.0 Hz, 2H), 3.91 (s, 1H), 3.74-3.71 (m, 4H), 3.09 (s, 1H), 3.62 (d, / = 7.2 Hz, 1H), 2.26-2.15 (m, 1H), 1.99- 1.89 (m, 1H), 1.76 (s, 2H), 1.34 (d, J = 4.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6298-96-0, its application will become more common.

Reference:
Patent; SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI; ZHANG, Xiaohu; ZHENG, Jiyue; MA, Haikuo; (184 pag.)WO2019/60860; (2019); A1;,
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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. 103-50-4, name is Benzyl ether, This compound has unique chemical properties. The synthetic route is as follows., name: Benzyl ether

General procedure: To a sealed tube containing the respective azobenzene 1 (0.25 mmol), dibenzyl ether 2 (0.75 mmol), Pd(OAc)2 (0.025 mmol), and DCE/AcOH (1:1, v/v, 1 mL in all) was added TBHP (1.5 mmol). After stirring vigorously at 60 C for 12 h, the mixture was evaporated under vacuum. The corresponding product 3 was isolated by silica gel column chromatography with a PE/EtOAc mixture as eluent.

According to the analysis of related databases, 103-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hong, Gang; Aruma, Alfred Njasotapher; Zhu, Xiaoyan; Wu, Shengying; Wang, Limin; Synthesis; vol. 48; 8; (2016); p. 1147 – 1158;,
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A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, s).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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Reference of 39538-68-6, 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. 39538-68-6, name is 2-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-methoxy-4-methylaniline (18, 10.9 mmol), bis-(2-chloroethyl)amine hydrochloride (12.0 mmol), potassium carbonate (15.2 mmol) in 1-butanol (5 mL) was refluxed under nitrogen overnight. The hot reaction mixture was filtered and the filtrate was concentrated under vacuum. The resulting residue was triturated with acetone and filtered to give 19 as an off-white powder (14% yield), mp 212-213 C (dec); 1H NMR (free base, CDCl3) delta 9.14 (s, 1H), 6.68-6.82 (m, 3H), 3.77 (s, 3H), 3.11-3.19 (m, 8H), 2.25 (s, 3H).

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

Reference:
Article; Vangveravong, Suwanna; Zhang, Zhanbin; Taylor, Michelle; Bearden, Melissa; Xu, Jinbin; Cui, Jinquan; Wang, Wei; Luedtke, Robert R.; MacH, Robert H.; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3502 – 3511;,
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