Month: June 2021

Synthetic Route 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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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., SDS of cas: 873980-68-8

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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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, Safety of 1-Bromo-3-fluoro-5-methoxybenzene

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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Synthetic Route 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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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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 4316-51-2

POCl3 (6 mL, 64.17 mmol) was carefully added to a solution of 4-methoxy-N,N-diphenylaniline (10 g, 36.32 mmol), DMF (5 mL, 64.85 mmol) and 50 mL of 1,2-dichloroethane. The mixture was refluxed for 4 h, then cooled to room temperature (r.t.), and poured into a saturated aqueous sodium acetate solution (100 mL). The product was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated by a rotary evaporator. The residue was purified by silica gel column chromatography using ethyl acetate: n-hexane (2:3) to give (1) (7.6 g, Yield: 69%). TOF/MS (ESI): found 326.1 (M+Na+). 1H NMR (300 MHz, CDCl3, delta): 9.79 (s, 1H, ArCHO), 7.68-6.89 (m, 14H, ArH), 3.83 (s, 3H, ArOCH3).

According to the analysis of related databases, 4316-51-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Giang, Ha Ngoc; Kinashi, Kenji; Sakai, Wataru; Tsutsumi, Naoto; Journal of Photochemistry and Photobiology A: Chemistry; vol. 291; (2014); p. 26 – 33;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, COA of Formula: C4H8Br2O

General procedure: 1,3-Dibromopropane (2.2 Kg, 10.9 mol) was slowly added to a stirred suspension of 264 g magnesium turnings (11 mol)In tetrahydrofuran (17.6 L).Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition is complete, the mixture is precooled to minus 50 degrees Celsius for two hours at minus 40 to 50 degrees Celsius,And the reaction mixture prepared from 2-chloropyridine was added.Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition was completed, the temperature was slowly raised to 60 C and stirred for 3 hours.The reaction mixture was concentrated under reduced pressure to 20 liters of n-hexane (20 L).The resulting solid was removed by filtration.Concentration of the filtrate followed by pressure distillation gave the desired target intermediate (1.16 Kg, 62%) as a colorless liquid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Zhejiang Xingyue Pharmaceutical Technology Co., Ltd.; Ying Lv; Chen Qingquan; Hu Junbin; (103 pag.)CN104177394; (2017); B;,
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Application of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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: 0.41 mmol of polyethylene glycol diamine,DIPEA105 mg, 4-fluoro-2- (2,6-dioxopiperidin-3-yl) ethindol-1,3-one,Add DMF 2mL, 90 C for 12 h. Cool to room temperature,Add water 20mL, ethyl acetate extraction,The extract is saturated with saline,Dried over anhydrous magnesium sulfate,Evaporated under reduced pressure,Silica gel column chromatography (methanol: dichloromethane 1; 10)Intermediate 7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; Jilin University; Lu Haibin; Wang Shihui; Li Haiyan; Wang Chunhe; Deng Jiayu; Feng Mingming; Guo Yu; Su Runping; Jin Xiangqun; (26 pag.)CN106543185; (2017); 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 145903-31-7 as follows. Application In Synthesis 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 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. COA of Formula: C18H21NO4

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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