Month: March 2021

Electric Literature of 59997-51-2, 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. 59997-51-2 name is 4,4-Dimethyl-3-oxopentanenitrile, 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.

Example 22. Preparation of Compound Nos. 142, 142a and 142b Step 2. To a solution of 4,4-dimethyl-3-oxopentanenitrile (2.22 g, 19.79 mmol) in ethanol (25 mL) was added hydrazine hydrate (1.06 g, 21.37 mmol) at 0 C. The reaction mixture was stirred at 100 C for 16 h. The reaction mixture was concentrated to remove the solvent, diluted with water, extracted with EtOAc (300 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford 5-(tert-butyl)-lH-pyrazol-3-amine (1.3 g, crude).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4-Dimethyl-3-oxopentanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; RAI, Roopa; GREEN, Michael, John; ANSARI, Amantullah; AGARWAL, Anil, Kumar; (216 pag.)WO2016/3827; (2016); A2;,
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Some common heterocyclic compound, 15996-76-6, name is 4-(Aminomethyl)benzonitrile hydrochloride, molecular formula is C8H9ClN2, 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-(Aminomethyl)benzonitrile hydrochloride

Triethylamine (4.932 mL, 35.583 mmol) was added to solution of 4-(aminomethyl)benzonitrile hydrochloride (5.000 g, 29.652 mmol) in dichloromethane (20 mL) at the room temperature, and the mixture was stirred for 10 mm at the same temperature. The reaction mixture was treated at the same temperature with Di-tert-butyl dicarbonate (6.795 g, 31.135 mmol) and stuffed for additional 5 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The title compound was used without further purification (tert-butyl (4-cyanobenzyl)carbamate, 6.850 g, 99.5 %, whtie solid).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15996-76-6, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); 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. 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 38487-85-3

General procedure: To the solution of anthranilonitrile S-1 (2.0 mmol) and Et3N (2.4 mmol) in 20 mL dry CH2Cl2 was added acryloyl chloride (2.2 mmol) at 0 C. The mixture was allowed to stir at room temperature. After completion of the reaction, the reaction was quenched with saturated NaHCO3 solution, then extracted with CH2Cl2, washed with brine, dried over MgSO4 and concentrated by evaporator affording amide S-2 without any further purification.

The synthetic route of 38487-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Tao; Zhou, Jia-Li; Li, Junpeng; Shen, Yuehai; Gao, Chuanzhu; Li, Ya-Min; Synthesis; vol. 50; 17; (2018); p. 3460 – 3466;,
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Electric Literature of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 zinc chloride (50 mL, 1.0 M in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1.0 M in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1 h then 1-bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1 N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%).

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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Nitrile – Wikipedia,
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Application of 194853-86-6, 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 194853-86-6 as follows.

EXAMPLES; Example 1; 4-[(Cyclopropylmethyl)(2-{[4-(1 ,1 -dimethylethyl)phenyl]oxy} ethyl)amino]-2- (trifluoromethyl)benzonitrile; A. 4-[(Cyclopropylmethyl)amino]-2-(trifluoromethyl)benzonitrile; A mixture of 4-fluoro-2-(trifluoromethyl)benzonitrile (9.45 g, 50 mmol), 1- cyclopropylmethanamine (5.0 g, 70 mmol), and potassium carbonate (10 g) was stirred for 12 h in acetonitrile (50 mL) at 55 0C. The mixture was cooled to 20 0C, filtered, and the filter-cake was washed with acetonitrile (3 x 25 mL). The filtrate was concentrated under vacuum to obtain 11.9 g (99%) of the title compound as a white EPO solid: 1H NMR (400 MHz, CDCI3) delta 7.53 (d, J = 8.6 Hz, 1 H), 6.83 (d, J = 2.4 Hz, 1 H), 6.65 (dd, J = 8.6, 2.4 Hz, 1H)1 4.62 (bs, 1 H), 3.02 (d, J = 7.1 Hz, 2H), 1.09 (m, 1 H), 0.61 (m, 2H), 0.27 (m, 2H).

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); A1;,
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Related Products of 90381-43-4,Some common heterocyclic compound, 90381-43-4, name is 7-Methoxy-2-naphthonitrile, molecular formula is C12H9NO, 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 90C 7-Methoxy-8-nitro-2-naphthalenecarbonitrile Example 90B (3 g, 16.4 mmole) in acetic anhydride (30 mL) at 0 C. was treated with fuming HNO3 (1.2 mL), and the resulting thick slurry was diluted with water (20 mL), stirred 20 min then filtered and dried in vacuo to provide 3.69 g of the title compound as a yellow solid. MS (DCI/NH3) m/e 246 (M+NH4)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Methoxy-2-naphthonitrile, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6258822; (2001); B1;; ; Patent; Abbott Laboratories; US6284796; (2001); B1;,
Nitrile – Wikipedia,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

(3R,4R)-N-( 1 -Cyanocyclopropyl)-4-(5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)-2-(5 – fluoropyridin-3 -yl)thiazol-4-yl)bicyclo [4.1 . 0]heptane-3 -carboxamide was synthesized following the same procedure as in Step H of Example 1 using (3R,4R)-4-(5-(4-(1,1- dioxidothiomorpholino)phenyl)-2-(5 -fluoropyridin-3 -yl)thiazol-4-yl)bicyclo [4.1 . 0]heptane-3 -carboxylic acid (0.180 g, 0.340 mmol, 1.00 equiv), DMF (5 mL), 1- aminocyclopropanecarbonitrile hydrochloride (0.202 g, 1.70 mmol, 5.00 equiv), HATU (0.324 g, 0.850 mmol, 2.50 equiv) and DIPEA (0.330 g, 2.55 mmol, 7.48 equiv). This resulted in 0.135 g (67%) of (3R,4R)-N-( 1 -Cyanocyclopropyl)-4-(5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)-2-(5 – fluoropyridin-3-yl)thiazol-4-yl)bicyclo[4. 1 .0]heptane-3-carboxamide as a yellow solid: MS (ES,m/z): 592.1 (M + 1).

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; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
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These common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, 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. Recommanded Product: 939-80-0

EXAMPLE 3a Preparation of 4-chloro-3-aminobenzonitrile A degassed solution of 40 mmol of 4-chloro-3-nitrobenzonitrile (starting material) and 40 ml of xylene are placed in an autoclave (volume: 200 ml).5.0 mmol of TPPTS (in the form of 9.2 g of an aqueous solution containing 0.546 mol of TPPTS/kg of solution) as phosphine and 2.4 g (60 mmol) of NaOH, 23.8 ml of H2 O and 1.0 mmol of PdCl2 are added. The pH isfrom 10.5 to 11.0. The autoclave is closed, evacuated and filled with nitrogen. The evacuationand filling with nitrogen is repeated twice, then the autoclave is filled with CO, evacuated and refilled with CO. The evacuation and filling with CO is repeated twice. The autoclave is subsequently pressurized with CO to a pressure of 120 bar and the mixture is heated to 100 C. while stirring. The reaction time is 20 hours. The mixture is subsequently cooled to room temperature, the autoclave is emptied and the organic phase is separated from the aqueous phase. The organic phase is filtered to remove traces of palladiumand evaporated under reduced pressure, with the desired product being purified, if desired by crystallization or chromatography.

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

Reference:
Patent; Hoechst Aktiengesellschaft; US5744643; (1998); A;,
Nitrile – Wikipedia,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 179897-89-3

To a solution of zinc chloride (50 mL, 1. OM in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1. OM in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1h, then 1- bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%). H NMR (400 MHz, CDC13) 8 7.38-7. 30 (m, 2H), 7.11 (dt, J=8.5, 1.4 Hz, 1 H), 2.49 (s, 2H), 0.90 (s, 9H).

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 179897-89-3.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
Nitrile – Wikipedia,
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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. 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2

Take carbazole monoaldehyde 0.502g (2mmol)Add about 3 mL of dichloromethane to a 100 mL round bottom flask to dissolve completely.Then, 0.3 g of p-aminophenylacetonitrile and 30 mL of ethanol were added to the flask.1.5 mL of TBAH (tetrabutylammonium hydroxide) was added dropwise as a catalyst.The progress of the reaction was monitored by thin layer chromatography and reacted at 80 C for 12 hours.The reaction mixture was cooled and a small amount of yellow precipitate was precipitated.Dry the organic phase to a yellow solid, dissolve it with a small amount of dichloromethane and pour it into a beaker.Add 100mL of ethanol and stir. A large amount of yellow solid precipitates and is quickly filtered.The solid obtained by suction filtration was washed three times with ethanol.The collected solid was dried and weighed 0.44 g of an orange-red solid with a yield of about 60%.

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 3544-25-0.

Reference:
Patent; Anhui University; Zhu Weiju; Fang Min; Liu Xiaonan; Ge Jialong; Li Cun; Wu Zhenyu; (12 pag.)CN108640867; (2018); A;,
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