Month: September 2021

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;,
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Reference of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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 sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); 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. 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C8H10BrNO

Preparation 40: 2-methoxy-5-methyl-4-(1 -methyl-1 A7-pyrazol-4-yl)aniline To a solution of 4-bromo-2-methoxy-5-methylaniline (Preparation 39, 350 mg, 1 .620 mmol) in EtOH (2.5 mL), toluene (2.5 mL) and water (2.5 mL) was added 1 -methylpyrazole-4- boronic acid pinacol ester (404 mg, 1 .944 mmol), sodium carbonate (343 mg, 3.24 mmol) and Pd(PPh3)4 (225 mg, 0.194 mmol). The reaction mixture was heated to 80C for 2.5 hours, under nitrogen. The reaction mixture was cooled to room temperature and diluted with EtOAc (30 mL), washed with water (30 mL) and brine (30 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-5% MeOH in DCM to give the title compound (140 mg, 36%). 1 H NMR (500 MHz, CDCI3): delta 7.56 (d, J = 0.5 Hz, 1 H), 7.39 (s, 1 H), 6.75 (s, 1 H), 6.63 (s, 1 H), 3.96 (s, 3H), 3.86 (s, 3H), 3.76 (br s, 2H), 2.27 (s, 3H). LCMS (ESI) Rt = 1 .13 minutes MS m/z 218.30 [M+H]+

The synthetic route of 873980-68-8 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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Electric Literature of 123652-95-9, 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. 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1. Model canadense amide quinones (DCA – CONH – 07) preparation, comprising the following steps:

The synthetic route of (3-Fluoro-4-methoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong University of Technology; Zhao Suqing; Zhang Bingjie; Feng Dongyan; Fang Yinglin; Wu Ke; Ling Huaying; Tan Qiting; Chen Yanting; Yang Yang; Zhao Jiawei; Ma Zhuolin; Hong Weiqian; (24 pag.)CN109651183; (2019); A;,
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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 162705-07-9 as follows. Product Details of 162705-07-9

General procedure: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

According to the analysis of related databases, 162705-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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Electric Literature of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 °C for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 °C, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

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

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, category: ethers-buliding-blocks

A solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1 H-pyrazol-4-ylboronic acid (41 mg, 0.083 mmol), 1-bromo-3- fluoro-5-methoxybenzene (20 mg, 0.10 mmol), Pd(PPh3)4 (10 mg, 0.0083 mmol), Na2003 (44 mg, 0.42 mmol) in degassed 1,4-dioxane and H20 (4:1, 1.7 mL) was heated at 85 C for 18 hours. LiOH (10 mg, 0.42 mmol) was added and the reaction was heated at 95 O under microwave radiation for 30 mm. i N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of ammonium formate) (60 to 80%). The product was lyophylised to give the title compound (16 mg, 0.028 mmol, 34%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 1.8 Hz, 1H), 8.03 (dd, J= 8.5, 1.8 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 6.94 -6.89 (m, 2H), 6.86 (d, J = 11.5 Hz, 1 H), 3.80 (5, 3H),3.35 (sept, J = 6.7 Hz, 1H), 2.32 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz): 552.1 [M+1].

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, 1-Bromo-3-fluoro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
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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 145903-31-7 as follows. Safety of 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine

Experimental Example 4 7-Methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (3.0 g), triethylamine (3.1 g) and bromoacetyl chloride (3.2 g) were reacted in the same manner as in Experimental Example 1 to give 4-bromoacetyl-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (2.5 g). IR numaxCHCl3 (cm-1): 1640 1 H-NMR(CDCl3, 100 MHz)delta: 2.75-2.94 (2H, m), 3.68-4.18 (4H, m), 3.80 (3H, s), 4.66-4.81 (2H, m), 6.65-7.58 (3H, m).

According to the analysis of related databases, 145903-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kirin Brewery Co., Ltd.; US5416066; (1995); A;,
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Reference of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4a (see general route 4, procedure H, M and K)2-(3-fluoro-4-methoxyphenyl)hydrazine; [00257] A room temperature solution of 3-fluoro-4-methoxyaniline (25.0 g, 177 mmol) in concentrated 12M aqueous hydrochloric acid solution (60 mL) was stirred for two hours, after which it was cooled to 0°C to which a solution of sodium nitrite (14.2 g, 205 mmol), in water (50 mL), was added, drop-wise over 45 minutes, with internal temperature monitoring such that the reaction temperature does not warm above 5°C. After stirring for one hour at 0°C, the reaction mixture was poured slowly into a 0°C pre-made solution of tin(II) chloride dihydrate (168 g, 744 mmol) in concentrated 12M aqueous hydrochloric acid solution (125 mL). The reaction mixture was allowed to warm up to room temperature, after which it was stored in the freezer overnight (12 hours), leading to the formation of a precipitate. This dark brown solid was successively washed with water (2 x 100 mL) and diethyl ether (3 x 100 mL), and dried to afford crude 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as a pasty brown solid (note that this crude solid can also be used directly in the next step). As part of the purification and isolation process, the crude hydrazine hydrochloride salt was reconstituted in water (100 mL) and 3M aqueous sodium hydroxide solution (200 mL), extracted with diethyl ether (2 x 200 mL), washed with successively with saturated sodium bicarbonate solution (2 x 100 mL), water (2 x 20 mL) and saturated sodium chloride solution (2 x 20 mL), dried (sodium sulfate), filtered and concentrated to afford 2-(3-fluoro-4- methoxyphenyl)hydrazine as a light yellow solid (15.0 g, 96.1 mmol, 54percent yield. 1H NMR (400 MHz, CDC13) delta (ppm): 6.87 (m, 1H), 6.66 (dd, 1H), 6.49-6.53 (m, 1H), 5.06 (br. s, 1H), 3.83 (s, 3H), 3.55 (br. s, 2H).[00258] A portion of 2-(3-fluoro-4-methoxyphenyl)hydrazine (5.00 g, 32.0 mmol) was dissolved in absolute ethanol (50 mL), to which a solution hydrogen chloride (15 mL, 2.5M in ethanol) was added. The resulting precipitate was filtered, washed with ethyl acetate (2 x 40 mL), and dried to afford 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as an off- white solid (4.7 g).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
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Reference of 112970-44-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112970-44-2 name is 2-Bromo-3-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
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