Category: nitriles-buliding-blocks

Synthetic Route of 151-18-8, These common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, 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.

Example 483 N-(3-(((2-cyanoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-6-methylpyridine-3-carboxamide To a solution of 4-(((6-methylpyridin-3-yl)carbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 56 (0.66 g, 2.0 mmol) and 3-aminopropionitrile (0.18 ml, 2.4 mmol) in DMF (15 ml), WSC (0.41 g, 2.4 mmol) and HOBt (0.32 g, 2.4 mmol) were added, and the mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, passed through a small amount of silica gel and evaporated under reduced pressure. Diethyl ether was added to the precipitated crystals, and the crystals were collected by filtration to give the title compound (0.60 g, yield 86%) as crystals. melting point 118-120 C. 1H-NMR (CDCl3): delta 1.55-1.80 (3H, m), 2.00-2.15 (2H, m), 2.15-2.30 (1H, m), 2.64 (3H, s), 2.74 (2H, t, J=6.6 Hz), 3.65-3.80 (3H, m), 4.00-4.15 (1H, m), 5.36 (1H, dd, J=9.3, 2.1 Hz), 7.26 (1H, d, J=7.5 Hz), 7.20-7.30 (1H, m), 8.07 (1H, dd, J=8.4, 2.7 Hz), 8.50 (1H, s), 9.09 (1H, d, J=2.7 Hz), 10.34 (1H, s).

Statistics shows that 3-Aminopropanenitrile is playing an increasingly important role. we look forward to future research findings about 151-18-8.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
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Application of 1147558-43-7, 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. 1147558-43-7, name is 4-Amino-3-chloro-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Chloro-5-fluoro-4-nitrobenzonitrile Sodium perborate tetrahydrate (131 g, 851 mmol) in acetic acid (200 mL) was heated to 60 C. A solution of 4-amino-3-chloro-5-fluorobenzonitrile (29.02 g, 170 mmol) in acetic acid (500 ml.) was added dropwise and the reaction was stirred at 60 C for 16 h. The LCMS the indicated the reaction showed -50% conversion. Additional sodium perborate tetrahydrate (14.4 g) was added and the reaction stirred at 70 C for 2 h. Then additional sodium perborate tetrahydrate (70 g) was added and the reaction was stirred at 80 C for 5 h, followed by RT for 2 days. The reaction was then poured into ice water and extracted with EtOAc (3x). The combined organic extracts were washed with H20 (2x), brine, dried over MgS04 and concentrated. When most of the acetic acid was evaporated, water was added to the residue. The orange precipitate was collected by filtration, washed with H20 and air dried to give the crude product as an orange solid. NMR showed the product contaminated with -10% of starting material. This product was used without any further purification.

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, 4-Amino-3-chloro-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2012/174342; (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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H8BrN

Exemplary compound 10 was prepared according to a synthetic scheme shown in FIG. 2. The synthetic procedures for preparing compound 10 are described in?Probes for Narcotic Receptor Mediated Phenomena. 34. Synthesis and Structure- Activity Relationships of a Potent mu-Agonist d-Antagonist and an Exceedingly Potent Antinociceptive in the Enantiomeric C9-Substituted 5-(3-Hydroxyphenyl)-N-phenylethylmorphan Series?, J. Med. Chem. 2007, 50, 3765-3776.

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; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; RICE, Kenner Cralle; JACOBSON, Arthur E.; LI, Fuying; GUTMAN Eugene S.; BOW, Eric W.; (99 pag.)WO2019/182950; (2019); A1;,
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Application of 103146-25-4,Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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.

Experiment 38; A range of experiments were conducted examining the resolution of diol with (+)-(S,S)-DTT. The general procedure is described below, and the details and results for each reaction are in table 1.Racemic diol (20 g, 58.4 mmol) was dissolved in approximately half of the solvent used for the experiment at 40 C. (+)-(S,S)-DTT.H2O (quantity specified in the table) was added as a solution in the other half of the solvent. The solution was held at 40 C. and was seeded within two minutes with crystals of (S)-diol.?(+)-(S,S)-DTT (approximately 5 mg). Crystallization typically began within 5-10 minutes after seeding. After 2 h at 40 C., the temperature of the solution was lowered to 20 C. over 2 h, and the solution was held at this temperature for a further 1 h. The product was then separated by filtration, washed with the appropriate solvent (2¡Á20 mL) and dried overnight at 60 C. under reduced pressure.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; US2009/69582; (2009); A1;,
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Reference of 243128-37-2, 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 98; 4-Fluoro-3-methoxy-benz lamine; Add 4-fluoro-3-methoxy-benzonitrile (2 g, 0. 01 mol), 10% palladium on carbon (0.400 g) and glacial acetic acid (120 ml) to a pressure vessel. Purge the reaction vessel with nitrogen, purge the reaction vessel with hydrogen, pressurize the reaction mixture with hydrogen (415 Kpa), seal the vessel, and agitate the reaction. After 8 hours stop the agitation, vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the 5% palladium on carbon and return the filtrate for product isolation. Concentrate the crude solution, re-dissolve in CH2C12 (80mL) and washe with 5N NaOH (35mL). Separate the organic and aqueous phases and extract the aqueous with additional CHUCK (20mL). Combine the organic solutions, dry, filter and concentrate to give the crude material 2. 08g (100%). The title compound as the major product (Rf = 0.12, 10% MeOH/CH2C12) is used without further purification. MS (ES+) 156.1 (M+1) +. lH NMR (400MHz, CDC13) : 8 7. 01 (dd, 1H, J= 8.2, 11.4), 6.95 (dd, 1H, J = 2. 1,8. 4), 6.80 (m, 1H), 3.89 (s, 3H), 3.82 (s, 2H), 1.54 (br s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
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Synthetic Route of 57381-34-7, The chemical industry reduces the impact on the environment during synthesis 57381-34-7, name is 5-Chloro-2-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation 10: 1-[5-Chloro-2-(4-methyl-piperazin-1-yl)-phenyl]-ethanone; STEP A; A mixture of 5-chloro-2-fluoro-benzonitrile (500 mg, 3.21 mmoi), K2CO3 (1.32 g, 9.64 mmol) and 1-methyi-piperazine (482 mg, 4.81 mmoi) in DMSO (6.4 ml) was stirred at 100C for 6 h and then partitioned between water and Et2O. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 98:2:0.1) to give 660 mg of 5-chloro-2-(4-methyl-piperazin-1-yl)-benzonitrile. Y= 87%

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, 5-Chloro-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAC S.R.L.; WO2007/113249; (2007); A2;,
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Synthetic Route of 143879-77-0, 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 143879-77-0 as follows.

a) 6-FLUORO-3-NITRO-2-PHERZOXYBENZONITRILE AND 2 FLUORO-3-NITRO-6-PHENOXYBENZONITRILE 2, 6-Difluoro-3-nitro-benzonitrile (10 g) and phenol (5.1 g) were dissolved in dimethylformamide (80 mL). Sodium hydride (60% in mineral oil) (2.2 g) was added and the mixture stirred for 10 h at room temperature under nitrogen. Both regioisomers were formed in a 2: 1 ratio in favour of the 2-phenoxy substituted desired product. Isopropyl alcohol was cautiously added followed by dilute hydrochloric acid (2M). The resulting solution was extracted with dichloromethane and the combined organic extracts washed with water. The organic phase was washed with brine, dried (magnesium sulphate), filtered and concentrated in vacuo. The residue obtained (9.7 g) was used in subsequent reaction without further purification. GCMS m/z = 258 [(M+ )]

According to the analysis of related databases, 143879-77-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2004/113303; (2004); A1;,
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Reference of 874-97-5, 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. 874-97-5 name is 3-Cyanobenzyl alcohol, 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.

3-Cyanobenzyl alcohol (308 mg, 2.32 mmol), N-hydroxyphthalimide (416 mg, 2.55 mmol) and triphenylphosphine (668 mg, 2.55 mmol) were dissolved in THF (8 mL). Diethyl azodicarboxylate (DEAD) (0.40 mL, 2.55 mmol) was added dropwise while stirring to the solution and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the residue washed with THF (4 mL) and dried under high vacuum. The crude product (1.24 g, 4.46 mmol) was dissolved in ethanol (8 mL) and hydrazine monohydrate (0.43 mL, 8.92 mmol) was added. The reaction was refluxed for 2 h and filtered. Ethanol was removed under reduced pressure and the residue suspended in ethyl ether. The ethyl ether layer was washed with 3% Na2CO3 (2*10 mL), brine (10 mL) and concentrated. The crude product (830 mg, 5.61 mmol) was dissolved in THF (15 mL) and cooled to 0 C. Lithium aluminum hydride (1 M in THF, 11.2 mL, 11.2 mmol) was added dropwise and the reaction was stirred overnight at room temperature. It was then quenched with methanol (10 mL) and water (2 mL). The mixture for stirred for a further 30 min. The salts were filtered off and the solvent removed by evaporation in vacuo. The crude product was purified by silica gel flash column chromatography using 20% MeOH/dichloromethane as eluent to afford the desired product as white solid (59 mg, 0.388 mmol, 17% over 3 steps). 1H NMR (CDCl3, 300 MHz): delta (ppm) 4.07 (s, 2H), 4.63 (s, 2H), 5.18 (s, 4H), 7.36-7.44 (m, 4H).

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

Reference:
Patent; NEWLINK GENETICS CORPORATION; Mautino, Mario; Jaipuri, Firoz; Marcinowicz-Flick, Agnieszka; Kesharwani, Tanay; Waldo, Jesse; (201 pag.)US10047066; (2018); B2;,
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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. 151-18-8, name is 3-Aminopropanenitrile, A new synthetic method of this compound is introduced below., name: 3-Aminopropanenitrile

A solution of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxy-phenyl)-1-[2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl]-1H-pyrazol-4-yl}-amide.dioxane (36 g, 57.0 mmol) in DCM (500 mL) was treated with 3-amino-propionitrile (5.0 mL, 68.4 mmol) and acetic acid (50 mL). The mixture was cooled in an ice bath before the addition of sodium triacetoxyborohydride (18.1 g, 85.4 mmol) portionwise. The reaction was allowed to warm to room temperature and stirred for 1.5 hours. The mixture was diluted with methanol and loaded onto a pad of Isolute SCX-2 which had been conditioned with MeOH. After flushing with MeOH, the product was eluted with 2M ammonia in MeOH. The basic fractions were combined and evaporated to afford pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (3-(5-chloro-2-difluoromethoxy-phenyl)-1-{2-[4-(2-cyano-ethylamino)-piperidin-1-yl]-2-oxo-ethyl}-1H-pyrazol-4-yl)-amide as a pale brown solid (31.1 g, 91%). LCMS (Method 3) [M+H]+=598.2, RT=2.25 min. 1H NMR (400 MHz, CDCl3) delta: (ppm) 9.84 (s, 1H), 8.78 (dd, 1H, J=1.6, 6.9 Hz), 8.69 (s, 1H), 8.58-8.55 (m, 1H), 8.40 (s, 1H), 7.68 (d, 1H, J=2.5 Hz), 7.41 (dd, 1H, J=2.7, 8.7 Hz), 7.28 (d, 1H, J=8.7 Hz), 7.28 (s, 1H), 7.00 (dd, 1H, J=4.2, 6.9 Hz), 6.50 (t, 1H, J=74.1 Hz), 5.08 (d, 1H, J=15.4 Hz), 5.02 (d, 1H, J=15.5 Hz), 4.37 (d, 1H, J=13.4 Hz), 3.88 (d, 1H, J=13.4 Hz), 3.22-3.12 (m, 1H), 3.02 (t, 1H, J=6.4 Hz), 2.98-2.86 (m, 2H), 2.82-2.72 (m, 1H), 2.52-2.46 (m, 2H), 1.96-1.83 (m, 2H), 1.36-1.20 (m, 2H).

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; Genentech, Inc.; Zak, Mark Edward; Ray, Nicholas Charles; Goodacre, Simon Charles; Mendonca, Rohan; Kellar, Terry; Cheng, Yun-Xing; Li, Wei; Yuen, Po-Wai; US2015/336962; (2015); A1;,
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Electric Literature of 99066-80-5, 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. 99066-80-5 name is Methyl 3-cyano-5-nitrobenzoate, 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.

10%Pd/C (0.9 g) was added to the solution of methyl-3-cyano-5-nitrobenoate (25 mmol) in MeOH (200 mL) and THF (100 mL). Then the solution was stirred at room temperature for 4 hours. After filtration, it was concentrated to give methyl-3-amine-5-cyanobenoate in 95% yield.

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

Reference:
Patent; Hutchison Medipharma Enterprises Limited; US2009/118292; (2009); A1;,
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