Tag: M.W=100-200

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;,
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Synthetic Route of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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.

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 366-99-4 as follows. SDS of cas: 366-99-4

Example 18; Synthesis of (4-Chloro-6-cyclohexylmethoxy-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl)-amine (114); To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by addition of NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexanes:ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp 98° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.36; MS (ESI): m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7).; Example 19; 6-Cyclohexylmethoxy-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4-diamine; Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70:30 hexanes:ethyl acetate), mp 181° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.17; MS (ESI): m/z 472 (M+H, 100), 261 (1.5).

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 20781-20-8

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80C for 24 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (1.73 g, 73%). 1H NMR (DMSOd6) 11.00 (1 H, s), 7.62 (1H, dd), 7.29 (1 H, d), 7.21 (1 H, d), 6.90 (1H, d), 6.56 (1 H, d), 6.43 (1 H, dd), 4.59 (2H, s), 3.79 (3H, s), 3.72 (3H, s). MS: [M-H+] 314.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
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Application 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.

A) (3-Trifluoromethoxy-phenylamino)-acetonitrile; A mixture of 3-(trifluoromethoxy)aniline (1.00 g, 5.64 mmol), bromoacetonitrile (745 mg, 6.21 mmol), sodium iodide (1.86 g, 12.4 mmol), and sodium carbonate (858 mg, 6.21 mmol) in CH3CN (15 mL) was heated at reflux for 18 h, then partitioned between water and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc gradient) afforded the title compound (904 mg, 74percent). Brown liquid, MS: 215.2 (M+H)+.

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; Adam, Jean-Michel; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; Ricklin, Fabienne; Roche, Olivier; US2010/22518; (2010); A1;,
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Application of 1535-75-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1535-75-7 as follows.

General procedure: To a mixture of chloral hydrate (19.9 g, 120 mmol) in water (400 mL) was added Na2SO4(142 g, 1 mol) in portions at 40 C. After becoming homogenous and clear, the mixture was cooled to room temperature. 1 (100 mmol) and concentrated HCl (9 mL) were then added to the resulting solution, followed by a mixture of hydroxylamine hydrochloride (20.9 g, 300 mmol) in water. The solution was heated at reflux for 8 h and then cooled to room temperature. The precipitate was collected and dissolved in a 10 % aqueous NaOH solution. The resulting mixture was filtered through a pad of Celite. The filtrate was acidified to pH = 3 with 6 N HCl. The precipitate was filtered and dried to give the desired product 2.

According to the analysis of related databases, 1535-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Chang-Chun; Wang, Bao-Lei; Liu, Jing-Bo; Wei, Wei; Li, Yu-Xin; Liu, Yang; Chen, Ming-Gui; Xiong, Li-Xia; Yang, Na; Li, Zheng-Ming; Chinese Chemical Letters; vol. 28; 6; (2017); p. 1248 – 1251;,
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Application of 393-15-7, A common heterocyclic compound, 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

General procedure: To a solution of N-[4-[5-(3-aminophenyl)-1,2,4-oxadiazol-3-yl]-3-chlorophenyl]-3-pyridinecarboxamide (VIc)(0.2 g, 0.51 mmol, 1 equiv) in THF (20 ml) was added phosgene(15wt % in toluene, 1.7 ml, 2.55 mmol, 5.0 equiv) and the reactionmixture was refluxed under N2 for 4 h. Upon the reactioncompletion as indicated by TLC the solution was concentratedunder reduced pressure, flushed with dry toluene. To theresulting residuewas added THF (20 ml), the appropriate aniline(0.77 mmol, 1.5 equiv) and DIPEA (0.132 g, 178 ml, 1.02 mmol, 2equiv) and the reaction mixture was refluxed under N2 overnight.Upon completion of the reaction as indicated by TLC, thesolution was concentrated, and the residue was purified bychromatography to give the desired final products (25-50).

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; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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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. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6781-17-5

EXAMPLE 1 A mixture of 1.9 g of 1-chloro-3-(4-fluorophenoxy)-propane, l.8 g of 2-(2-ethoxyphenoxy)ethylamine, 0.53 g of sodium carbonate and 60 ml of dimethylformamide was heated at 80-90 C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride, M.P. 78-82 C. Recrystallization from ethanol-benzene gave white crystals, M.P. 84-86 C.

According to the analysis of related databases, 6781-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4010280; (1977); A;,
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22236-08-4, name is 3-(Difluoromethoxy)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. SDS of cas: 22236-08-4

To a solution of 3- (difluoromethoxy) aniline (318 mg, 2.0 iranol) and pyridine (633 mg, 8.0 iranol) in N-methylpyrrolidone (2 mL) was added phenyl chloroformate (251 muL, 2.0 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 2-chloro-4- [ (5-methyl-5H-pyrrolo [3, 2-d]pyrimidin-4- yl) oxy] aniline (275 mg, 1.0 mmol) was added to the reaction mixture, and the mixture was stirred at 800C for 8 hr. The reaction mixture was diluted with water, basified with IN aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=80/20->0/100) , and then silica gel column chromatography (hexane/ethyl acetate=80/20-»0/100) and recrystallized from diisopropyl ether to give the title compound (229 mg, 50%) as a white solid. 1H-NMR (DMSO-de, 300 MHz) delta 4.11 (3H, s) , 6.61 (IH, d, J = 3.0 Hz), 6.81 (IH, dd, J = 8.0, 2.1 Hz), 7.19 – 7.23 (IH, m) , 7.22 (IH, t, J = 74.1 Hz), 7.31 (IH, dd, J = 9.0, 2.7 Hz), 7.35 (IH, t, J = 8.0 Hz), 7.49 (IH, t, J = 2.1 Hz), 7.56 (IH, d, J = 2.7 Hz), 7.80 (IH, d, J = 3.0 Hz), 8.17 (IH, d, J = 9.0 Hz), 8.30 (IH, s), 8.43 (IH, br s) , 9.60 (IH, br s) .

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/4749; (2007); A1;,
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Some common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-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. SDS of cas: 19500-02-8

2-Methoxy-4-bromotoluene; Crude 2-methoxy-6-amino-toluene (max. 120 mmol) was suspended in HBr (48%, 48 ml) and water (120 ml) and cooled to 0C in an ice bath. Sodium nitrite (9.2 g) in water (24 ml) was added dropwise to the cold mixture, which turned yellow then brown. After 10 min, excess nitrite was destroyed by addition of urea (0.08 g) and the mixture was rapidly filtered into cold (0C) acetone (480 ml) to give a bright yellow solution. CuBr (99.999%, 18.89,131 mmol) was then added portionwise and the resulting mixture stirred at 0C for 3h. Gas evolution was observed. The mixture was allowed to warm to ambient temperature, and then concentrated in vacuo. Dichloromethane was then added and the mixture washed with sat. aq. sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulphate and concentrated in vacuo to give the product (23.1 g, 96%) as a red oil. No.H (CDCl3; 250MHz) 7.18-6.77 (3H, m, aromatics), 3.83 (3H, s, OCH3), 2.32 (3H, s, CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19500-02-8, its application will become more common.

Reference:
Patent; ARAKIS LTD.; WO2005/103019; (2005); A1;,
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