Author: Jessica.F

These common heterocyclic compound, 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, 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. Application In Synthesis of 4-Methoxy-N,N-dimethylaniline

General procedure: Under an atmosphere of N2, KOt-Bu (2.2 mmol), dioxane (0.9 mL), DMSO (1.65 mmol), tertiary amine 1 (0.55 mmol), and aryl halide 2(1.65 mmol) were successively added to a Schlenk reaction tube. The mixture was stirred vigorously at 80-120 C for 12 h. Then the mixture was diluted with EtOAc, washed with sat. brine, and dried (anhyd Na2SO4). Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (petroleum ether and petroleum ether-EtOAc, 100:1 for the methoxy group derived products) to give pure products 3.

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

Reference:
Article; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
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Electric Literature of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

This material (1.8 g) is taken up in methanol (100 ml) containing concentrated hydrochloric acid (0.6 ml), treated with 10% palladium on carbon and hydrogenated at 45 psi for 8 hours. The catalyst is filtered off and the solvent removed at reduced pressure to afford 4-tert-butoxypiperidine hydrochloride.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIBA-GEIGY AG; EP475895; (1992); 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. 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;,
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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 143-24-8 as follows. Computed Properties of C10H22O5

The bis (trifluoromethylsulfonyl) imide lithium described in(Hereinafter referred to as LiNTf 2) and G 4 or G 3 Bu were weighed in amounts listed in Table 1 and placed in a 50 mL round bottom flask,In this case, the mixture was stirred at 20 C. for 6 hours under a nitrogen atmosphere to obtain a single phase colorless transparent liquid without phase separation.

According to the analysis of related databases, 143-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANEKA CORPORATION; SAITO, KEN; (13 pag.)JP2016/6022; (2016); A;,
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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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, This compound has unique chemical properties. The synthetic route is as follows., name: 1,11-Diamino-3,6,9-trioxaundecane

Synthesis of Intermediate J To a solution of 2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethanamine (646 mg, 3.36 mmol) in anhydrous i-PrOH (10.0 mL) was added triethylamine (255 mg, 2.52 mmol, 349 muL) and the reaction mixture cooled to 0 C. A solution of [(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] carbonochloridate (800 mg, 1.68 mmol) in DCM (10 mL) was added dropwise to the reaction mixture over 10 minutes. The resultant solution was stirred at 0 C. for 2 hours then warmed to room temperature and stirred another 4 hours until completion of the reaction was indicated by TLC. The reaction mixture was concentrated under reduced pressure and purified via flash chromatography with an eluent of methanol/DCM (1:4) to afford the product [(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]carbamate (823 mg, 1.30 mmol, 77.4% yield).

According to the analysis of related databases, 929-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Preceres Inc.; Heidebrecht, JR., Richard Wayne; Svenson, Sonke; Wiegand, Roger; Hwang, Jungyeon; Beaudoin, Jen; Zhong, Cheng; (181 pag.)US2017/325457; (2017); 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-2-(2-bromoethoxy)ethane

Step 1 ): (0666) To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 muIota_ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 muIota_ of bis (2- bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product Compound 3 (46%). 1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1 H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 – 3.76 (m, 4H), 3.44 – 3.31 (m, 1 H), 3.29 – 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1 H), 2.46 (d, J = 16.7, 1 H), 1 .24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDCI3) delta 1 66.64, 154.05, 152.18, 127.1 0, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 1 6.36. MS: 274 (M + 1 ). Anal. Calcd. for C15H19N3O2: C, 65.91 ; H, 7.01 ; N, 15.37; Found. 65.81 , H, 6.66, N, 15.26.

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 5414-19-7.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSITUTE, INC.; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; LEWIS, Timothy, A.; WU, Xiaoyun; GREULICH, Heidi; MEYERSON, Matthew; ELLERMANN, Manuel; LIENAU, Philip; EIS, Knut; WENGNER, Antje, Margret; KOPITZ, Charlotte, Christine; LANGE, Martin; (88 pag.)WO2018/141835; (2018); A1;,
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Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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: C8H9F2NO2

Example 1233-{ 13-(2,6-difluoro-3,5-dimethoxyphenyl)-2,8-dioxo-2,3,4,7,8,9-hexahydro-1H- pyrrolo j3?,2?:5,6j pyrido 14,3-d jpyrimidin-1-ylj methyl}benzonitrile Step 1: N-[(4-chloro-1-{[2-(trimethylsilyl)ethoxyJmethyl}-JH-pyrrolo[2, 3-bJpyridin-5- yl)methylJ-2, 6-dijluoro-3 , 5-dimethoxyaniline To a solution of sodium triacetoxyborohydride (6.2 g, 29 mmol) in trifluoroacetic acid (10.0 mL, 1.30E2 mmol) at 0 C was added a solution of 2,6-difluoro-3,5-dimethoxyaniline (1.52 g, 8.03 mmol) in methylene chloride (10 mL), followed by a solution of 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl} -1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (Example 106, Step 1: 2.27 g, 7.30 mmol) in methylene chloride (40 mL, 700 mmol). The reaction mixture was stirred at 0 C for 1 h then poured into a cold aqueous solution of NaHCO3 and then extracted with methylene chloride. The organic phase was washed with brine then dried over Na2SO4 and concentrated. The residue was purified by flash chromatography eluted with 0 to40 % EtOAc in DCM to give the desired product as a yellow oil which solidified on standing (3.32 g, 94 %). LC-MS calculated for C22H29C1F2N3O3Si (M+H) mlz: 484.2; found: 484.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 651734-54-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; ZHANG, Colin; HE, Chunhong; SUN, Yaping; LU, Liang; QIAN, Ding-Quan; XU, Meizhong; ZHUO, Jincong; YAO, Wenqing; WO2014/7951; (2014); A2;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., COA of Formula: C7H17NO2

/V./V-Diisopropylethylamine (3.397 mL, 19.5 mmol) followed by 3,3-diethoxypropan-l- amine (3.154 mL, 19.5 mmol) were added to a solution of 4-chloro-l-fluoro-2- nitrobenzene (1.765 mL, 15 mmol), in iPrOH (35 mL) and heated at 80 C for 4.5 h. After cooling to rt, the reaction mixture was diluted with EtOAc (100 mL), washed successively with LLO (acidified to -pH 6 with 0.01 M aqueous HC1, 4x) and brine (1 x, 100 mL each), dried (MgS04) and the solvent removed under reduced pressure to afford the crude product as an orange solid (4.308 g, 97%). ‘H NMR (400 MHz, CDCls): d 8.29 (br s, 1H), 8.17 (d, J = 2.6 Hz, 1H), 7.37 (ddd, J = 9.2, 2.6, 0.6 Hz, 1H), 6.83 (d, J = 9.2 Hz, 1H), 4.65 (t, J = 5.0 Hz, 1H), 3.76-3.65 (m, 2H), 3.59-3.49 (m, 2H), 3.44-3.37 (m, 2H), 2.07-2.01 (m, 2H), 1.24 (t, J = 7.0 Hz, 6H). LRMS (ESI+) m/z 324.9 [M+Na]+

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; REVIRAL LIMITED; GOOD, James; (48 pag.)WO2019/122928; (2019); A1;,
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These common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, 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. HPLC of Formula: C5H13NO

The following Examples were prepared according to Method 5 (Example 54) above using 8-chloro-A/-(2-methoxy-4-(1 -methyl-1 H-pyrazol-4-yl)phenyl)pyrido[3,4- d]pyrimidin-2-amine (Example 94) and the appropriate amine as described. Where the amine hydrochloride was used, triethylamine (190uL, 0.373 mmol) was also added to the reaction. The crude reaction residues were purified as above or according to one of the following methods: Method A: Silica gel column chromatography eluting with 0-5% or 0-10% MeOH in DCM. Method B: Silica gel column chromatography eluting with 0-5% MeOH in EtOAc. Method C: Silica gel column chromatography eluting with 0-70% EtOAc in cyclohexane followed by reverse phase preparative HPLC eluting with 10-90% MeOH in water (0.1% formic acid).

The synthetic route of 2-Methoxy-2-methylpropan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; SOLANKI, Savade; WOODWARD, Hannah; NAUD, Sebastian; BAVETSIAS, Vassilios; SHELDRAKE, Peter; INNOCENTI, Paolo; CHEUNG, Jack; ATRASH, Butrus; WO2014/37750; (2014); A1;,
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Reference of 2674-34-2, 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 2674-34-2 as follows.

Into a 200-mL three-neck flask were put 8.9 g (30 mmol) of 1,4-dibromo-2,5-dimethoxybenzene, 10 g (72 mmol) of 2-fluorophenylboronic acid, 15 mL of toluene, 15 mL of diethylene glycol dimethyl ether (diglyme), and 60 mL of a sodium carbonate aqueous solution (2.0 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.69 g (0.60 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 2 hours. The mixture was cooled down to room temperature and degassed again under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. After the heating, 0.69 g (0.60 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to this mixture, and the mixture was heated at the same temperature for 5 hours. After the heating, 2.0 g (14 mmol) of 2-fluorophenylboronic acid was added to this mixture, and the mixture was further stirred at the same temperature for 3 hours. After the heating, the mixture was cooled down to the room temperature and degassed under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. This mixture was heated to 80 C., 0.64 g (0.55 mmol) of tetrakis(triphenylphosphine)palladium(0) and 3.0 g (21 mmol) of 2-fluorophenylboronic acid were added to the mixture, and the mixture was stirred at the same temperature for 2 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a compound. The obtained compound was recrystallized with toluene to give 2.5 g of a target. The compound obtained by the concentration of the filtrate was purified by column chromatography (a developing solvent: a mixed solvent of hexane and ethyl acetate in a ratio of 30:1) to give 0.3 g of a target. The targets were 2.8 g in total, and the yield was 29%. A synthesis scheme of the above synthesis method is shown in (A-1) below.

According to the analysis of related databases, 2674-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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