Tag: M.W=100-200

These common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, 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: 2,2-Diethoxyacetonitrile

To a vial was added 2,2-diethoxyacetonitrile (XIX) (1.0 g, 7.74 mmol) dissolved MeOH (7.74 mL) followed by addition of MeONa/MeOH (0.18 mL, 0.77 mmol) dropwise. The reaction was stirred at room temperature for 20 h. HOAc (44.3 muL, 0.77 mmol) was added until pH=7-8 (using pH strips). (4-Bromo-3-fluoro-phenyl)methanamine hydrochloride (XX) (1.86 g, 7.74 mmol) was added and stirred at 40 C. for 4 h. The solvent was removed under vacuum. Sulfuric acid (12.6 mL, 232.3 mmol) was added and stirred at 40 C. for 16 h. NH4OH (30.8 mL, 240.0 mmol) was added dropwise at 0 C. The solvent was removed under vacuum and the residue was purified by C18 silica gel (240 g) [0?50% H2O/MeCN (0.1% Formic acid)] to produce 6-bromo-7-fluoro-isoquinolin-3-amine (XXI) (1.33 g, 5.50 mmol, 71.1% yield) as an off-white solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 6.07 (2H, s), 6.61 (1H, s), 7.76 (1H, d, J=9.33 Hz), 8.01 (1H, d, J=6.86 Hz), 8.80 (1H, s); ESIMS found for C9H6BrFN2 m/z 242.9 (81BrM+H).

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

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Hofilena, Brian Joseph; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; (149 pag.)US2019/125740; (2019); A1;,
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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 4435-14-7 as follows. HPLC of Formula: C8H13N

The isopropyl cyclohexylacetimidate hydrochloride used as the starting material was prepared as follows: In a manner analogous to that described in Example 1, from cyclohexylacetonitrile, there was obtained isopropyl cyclohexylacetimidate hydrochloride in the form of a pale pink solid of melting point 108-110 C.

According to the analysis of related databases, 4435-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US5399712; (1995); A;,
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Electric Literature of 327056-73-5, 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. 327056-73-5 name is 3-Chloro-5-fluorobenzonitrile, 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 solution of 19 (1.07 g, 5 mmol), 16 (1.3 g, 7.56 mmol), K2CO3 (2.07 g, 15.0 mmol) and NMP (10 mL) was stirred and heated to 110 C. for 6 h. The reaction mixture was cooled to RT and diluted with H2O (50 mL) and twice extracted with EtOAc. The combined organic extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (10:90) to afford 0.328 g of 31.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2007/88053; (2007); 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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)phenylacetonitrile

To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95%). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+M).

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; Goble, Stephen D.; Yang, Lihu; Zhou, Changyou; Kothandaraman, Shankaran; Guiadeen, Deodialsingh; Butora, Gabor; Pastemak, Alexander; Mills, Sander G.; US2007/117797; (2007); A1;,
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21883-13-6, name is 4-Methoxy-2-methylbenzonitrile, belongs to nitriles-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: 21883-13-6

Example 3 Methyl 3-(4-methoxy-2-methylphenyl)-2-methyl-3-oxopropanoate Methyl 2-bromopropanoate (0.3 mL) was added to anhydrous tetrahydrofuran (100 mL) of zinc powder (11 g) under argon gas atmosphere, followed by refluxing by heat for 15 minutes. 4-methoxy-2-dimethylbenzonitrile (5.0 g) was added to the resultant reaction solution, and further methyl 2-bromopropanoate (15 mL) was dropped thereinto taking 40 minutes, followed by refluxing by heat for 1 hour. The resultant reaction solution was cooled into room temperature, and was diluted with tetrahydrofuran (50 mL) and 50% potassium carbonate solution (30 mL), followed by stirring for 30 minutes. The supernatant of the reaction solution was separated, and concentrated under reduced pressure. The residual was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated saline solution, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. Methanol (110 mL) and IN hydrochloric acid (33 ml) were added to the residue, and stirred at room temperature for 15 hours. The resultant reaction solution was concentrated under reduced pressure, was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0?71:29), to thereby obtain a title compound (5.4 g) having the following physical properties. TLC: Rf 0.55 (hexane:ethyl acetate=3:1); 1H-NMR(300 MHz, CDCl3): delta 7.72 (d, J=9.3 Hz, 1H), 6.81-6.73 (m, 2H), 3.85 (s, 3H), 3.68 (d, J=0.6 Hz, 3H), 2.54 (s, 3H), 1.56 (d, J=0.6 Hz, 3H), 1.45 (dd, J=7.2, 0.3 Hz, 3H).

The synthetic route of 21883-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1961754; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, belongs to nitriles-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 326-62-5, Computed Properties of C8H6FN

General procedure: To a solution of 9 (20 mmol) in anhydrous DMF (100 mL) was added appropriate aryl acetonitriles (22 mmol) at room temperature. After the mixture was stirred for 0.5 h, 60% NaH (1.0 g, 24 mmol) was added portion wise at -10C under a nitrogen atmosphere. The whole mixture was stirred at the same temperature for 1 h, warmed to room temperature and then reacted for 48-72 h. The resulting mixture was acidified with acetic acid under ice cooling and concentrated under reduced pressure to afford the crude intermediate 10. Then, without further purification, EtOH (300 mL) was added at room temperature. After stirred for 0.5 h, 10% NaOH (100 mL) was added dropwise under ice cooling. The reaction mixture was then stirred at room temperature for 24-48 h and then acidified to pH 5-6 with acetic acid. After most of the solvent was removed under reduced pressure, the resulting residue was poured into water and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude product, which was first purified by flash chromatography (eluent: CH2Cl2) and followed by recrystallization from MeOH or AcOEt, to afford target compounds 3a-h.

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, 2-(2-Fluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Guo-Shen; Du, Fen; Zhao, Tian-Sheng; Xiong, Yuan-Zhen; Indian Journal of Heterocyclic Chemistry; vol. 28; 2; (2018); p. 255 – 260;,
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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. 193290-27-6, name is 3-(2-Hydroxyethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(2-Hydroxyethyl)benzonitrile

To a cooled (0 C) solution of S15 (150 mg, 1.019 mmol) (which was prepared as described in Lee, B. C; Choe, Y. S.; Lee, K. H.; Kim, B. T.; Chi, D. Y. J. Labelled Compd. Rad. 2001, 44, S404) in CH2C12(8 mL) were added MsCl (0.16 mL, 2.038 mmol) and Et3N (0.43 mL, 3.057 mmol). After stirring for 0.5 h at 0 C, brine was added. The layers were separated and the aqueous layer was extracted with CH2C12. The combined organic layers were dried over anhydrous Na2S04and concentrated in vacuo. To a cooled (0 C) solution of the crude mixture in THF/DMF (4/1, 15 mL) were added triphenylmethylsilane (TrtSH) (1.13 g, 4.076 mmol) and NaH (60% dispersion in mineral oil, 163 mg, 4.076 mmol). After stirring for 16 h at 25 C, the reaction mixture was quenched by the addition of saturated NH4C1 solution and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexanes = 1/30) to afford S16 (1.8 g, 94% for two steps)

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 193290-27-6.

Reference:
Patent; HONG Jiyong; LUESCH Hendrik; WO2015/200699; A2; (2015);,
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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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 77326-36-4

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

According to the analysis of related databases, 77326-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
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Application of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, 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.

3-(2′-Aminopyrimidin-4′-yl)-1H-indole (80 mg, 0.38 mmol),KOH (30mg, 0.48mmol)With 5-bromopenteronitrile (0.23g, 1.43mmol)Miscible in DMF (6mL),And stirred at 40 C for 15 h,The resulting mixture was concentrated under reduced pressure to about 1/2 volume.Pour into H2O (20 mL),Extracted with EtOAc (15 mL¡Á3).The organic phase was combined and washed with saturated brine (20 mL).Anhydrous Mg2SO4 is dried,Silica gel layer filtration,The filtrate is evaporated to dryness.The resulting solid was dissolved in methanol (10 mL).Dry hydrogen chloride gas was passed at 0 C and stirred for 11 h, then evaporated to dryness.The resulting yellow solid was redissolved in methanol (10 mL).Slowly add 25% concentrated ammonia (1 mL) and stir for 3 h.The mixture is concentrated,Purified by column chromatography,Obtained a yellow solid (89 mg, yield 85%, a compound of formula I-26).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Jiang Tao; Dong Xueyang; Zhang Lijuan; Tong Sheng; Yin Ruijuan; Zhang Hailin; (26 pag.)CN108218838; (2018); A;,
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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. 3032-92-6, name is 4-Ethynylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C9H5N

General procedure: An8 ml glass vial was charged with the alkyne (0.3 mmol), aryl iodide(0.25 mmol), K2CO3 (79 mg, 0.5 mmol), CuI (2.4 mg, 5 mol%), 3-Pphen(3.9 mg, 5 mol%), PEG-400 (20 mg, 20 mol%) and water (1 ml) under argon. The vial was closed with a Teflon cap and the heterogeneous reaction mixture was stirred at 100 C for 3 or 6 h (see Scheme 1). After cooling, the mixture was extracted with EtOAc, the extract was dried overMgSO4. After evaporation, the residue was purified by flash chromatography on silica gel with light petroleum as the eluent. 1H and 13C NMR spectroscopic data of products were consistent with those describedpreviously.13

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; Mitrofanov, Alexander Yu.; Beletskaya, Irina P.; Mendeleev Communications; vol. 29; 4; (2019); p. 378 – 379;,
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