Category: nitriles-buliding-blocks

Reference of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A four-necked flask equipped with stirrer and thermometer was charged with 219 g of a solution containing 21.9 g (0.064 mol) of [()-4- [4-DIMETHYLAMINO-L-] (4′- [FLUOROPHENYL)-1-HYDROXYBUTYL]-] 3-hydroxymethylbenzonitrile in toluene. Then, 14.6 g (0.128 mmol) of vinyl butyrate, 5.07 g (0.128 mol) of pyridine, 7.89 g (0.064 mol) of benzoic acid and 2.19 g of an immobilized enzyme (Novozym 435) were added into the above mixture. The reaction mixture was allowed to warm up to [60 C] and stirred for 15 hours under a slight flow of nitrogen and stirring was stopped. The enzyme was filtrated off from the reaction mixture with Kiriyama funnel, and washed with 50 g of toluene. The combined toluene layer was washed twice with water (255 ml, 265 ml) and concentrated to give 14.9 g of [(R)-5-CYANO-2-] [dimethylamino- (4′-fluorophenyl)- hydroxybutyl] benzyl butyrate benzoic acid salt. To a mixture of 4.0 g of (R) -5-Cyano-2- [dimethylamino- (4′-fluorophenyl)- hydroxybutyl] benzyl butyrate benzoic acid salt (7.48 mmol), 40 ml of water and 40 ml of toluene were added 1.26 g of 30% sodium hydroxide (9.45 mol) with stirring, the mixture was kept stirring for 30 minutes. After stirring, the mixture was allowed to stand and the toluene layer was separated. The toluene layer was washed with 40 ml of water and concentrated at [40 C] under reduced pressure, to thereby obtain 2.7 g of (R) -5-Cyano-2- [dimethylamino- [(4′-FLUOROPHENYL)-HYDROXYBUTYL]] benzyl butyrate. 1H NMR (400 MHz. CDC13) [A] (ppm): 7.69 [(1H,] s), 7.68-7. 56 (2H, m), 7.36-7. 23 (2H, m), 7.02-6. 90 (2H, m), 5.41 [(1H,] d, J [14.] 9 Hz), 4.99 [(1H,] d, J [14.] 6 Hz), 2.59- 2.42 [(1H,] m), 2.40-2. 30 (3H, m), 2.26 (2H, dt, J= 7.3 Hz, 1.5 Hz), 2.18 (6H, s), 1.68- 1.57 (2H, m), 1.67-1. 46 (2H, m), 0.93 (3H, t, [J =] 7.6 Hz).

The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); 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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H10BrN

To a stirred solution of 2-(4-bromophenyl)-2-methylpropanenitrile (11.88 g, 53.0 mmol, 1.0 eq.) in THF (150 ml) was added dropwise a solution of B in THF (1.0 N, 159 ml, 159.0 mmol, 3.0 eq.) at an ice-water bath temperature, and the resultant mixture was heated to reflux for 4 hours. The reaction mixture was cooled to ambient temperature, and was concentrated to dryness. The obtained residue was dissolved in methanol, and was heated to reflux for additional (0135) 1 hour. The reaction mixture was concentrated to dryness again, and was treated with water. The aqueous phase was extracted with EA, washed with brine, dried over Na2S04, and was concentrated to dryness. The crude material 2-(4-bromophenyl)-2-methylpropan- 1 -amine was used directly in next step without further purification

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; PHARMABLOCK SCIENCES (NANJING), INC.; LIU, Liu; LI, Jin; YANG, Minmin; (126 pag.)WO2019/173804; (2019); A1;,
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These common heterocyclic compound, 89001-53-6, name is 2-Methyl-4-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. Product Details of 89001-53-6

solution of the 2-methyl-4-nitrobenzenecarbonitrile (160.0 g, 0.98 mol) in 80% sulfuric acid (700 mL) was heated in an oil bath at 100 C for 2 hours, cooled to room temperature and poured onto crushed ice. The resulting solid was filtered and used without purification in the next step.

The synthetic route of 2-Methyl-4-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/69245; (2004); 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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

3.123. Compound 111: (lR,2R)-N-[6-(2-chloro-4-cyano-6-fluoro-N-methyl-anilino)-l-methyl- 3.123.1. Step i): 4-amino-3-chloro-5-fluoro-benzonitrile A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) is stirred at 70C for approximately 16 h. The mixture is concentrated. H20 is added to the residue and the solid product is filtered off and washed (sat. NaHCC>3 and H20). To eliminate H20, THF is added and removed under reduced pressure to yield the desired product (Int. 21). 3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte

The synthetic route of 63069-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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Reference of 327056-73-5, The chemical industry reduces the impact on the environment during synthesis 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

5-Fluoro-3-chloro-benzonitrile (Ig, 6.4 mmol) was dissolved in DMSO (20 ml) followed by addition Of K2CO3 (1.3g, 9.6 mmol) and 1 -methyl piperazine (1.4 ml, 12.8 mmol). The reaction mixture was heated at 80 0C for 20 hours. Diethyl ether was added to the crude material (10 ml) then acidified with IN HCl. A precipitate was filtered off from the crude reaction mixture to give 3-chloro-5-(4-methyl- rhoirhoerazin-l-yl)-benzonitrile (1.4g, 93% yield) as a white solid (LC/MS: Rt 1.83 [M + H]+ 236, acidic method).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/70195; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 92664-05-6, name is Potassium 1-cyano-3-ethoxy-2,3-dioxopropan-1-ide, 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 92664-05-6, COA of Formula: C6H6KNO3

To a stirring suspension of crude 5-hydrazi- nylisoquinoline (prepared from Example 25 step a, 6.0 g, 37.7 mmol) and potassium 1-cyano-3-ethoxy-3-oxoprop-1- en-2-olate (8.1 g, 45.2 mmol) in ethanol (36 mE) was added a solution of 6 N aqueous hydrochloric acid (7.7 mE, 45.2 mmol) and deionized water (10 mE). The reaction mixture was heated at 90 C. for 5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resulting residue was extracted with 2:1 chloroforml iPrOR. The organic layer was washed with aqueous saturated sodium bicarbonate and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting solid was suspended in dichloromethane/diethyl ether and the yellow solid was collected by filtration to give the desired product (3.14 g, 11.1 mmol, 30%)

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, Potassium 1-cyano-3-ethoxy-2,3-dioxopropan-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (2018); A1;,
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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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Oxobutanenitrile

General procedure: In a 250 mL RBF, 3-aminobut-2-enenitrile (2.0 g, 0.24 mole) was added to a stirred solution of cyclohexyl hydrazine hydrochloride (4.0 g, 0.026 mole) and acetic acid (0.1 mL) in ethanol (60 mL). The reaction was refluxed for 6 h. Crude was evaporated and loaded on column to elute out product at 40% ethyl acetate in hexane. (1.74 g, 40%)

According to the analysis of related databases, 2469-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sharma, Swagat; Kozek, Krystian A.; Abney, Kristopher K.; Kumar, Sushil; Gautam, Nagsen; Alnouti, Yazen; David Weaver; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 791 – 796;,
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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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 78881-21-7

To the ice-cold trifluoroacetic anhydride (60 mL) was added 4-amino-3-methyl-benzonitrile (14.33 g, 0.108 mol) in portion. The resulting white slurry was stirred at 0 C. for 30 min. Then ammonium nitrate (17.28 g, 0.216 mol) was added. The reaction mixture was allowed to stir at 0 C. for 1 h and at room temperature for 14 h. After removal of most solvent, the reaction mixture was cooled with ice and quenched with ice. The yellow precipitate was filtered, washed with cold water, and dried under vacuum. The crude product (15.5 g, 52% yield, and ca. 80% pure) was used for the next step without purification. 1H NMR (300 MHz, CD3OD) delta 8.05 (1H, s), 7.74 (1H, s), 2.30 (3H, s). LRMS (neg. ESI, (M-H)-) m/z 272.

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 78881-21-7.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
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Synthetic Route of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 oC. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1:1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 oC (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-1H-indazol-3-amine (549.0 g, 75% yield) as a brick red-colored solid.1H NMR (400 MHz, CDCl3): d 10.36 (bs, 1H), 8.20 (d, J = 8.4 Hz, 1H), 7.07 (d, J = 8.40 Hz, 1H), 4.73 (bs, 2H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichloro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; GILLIS, Eric P; PARCELLA, Kyle E.; PATEL, Manoj; PEESE, Kevin M; (277 pag.)WO2020/84492; (2020); A1;,
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Some common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, molecular formula is C6H11NO2, 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. Computed Properties of C6H11NO2

In a 2 L, three-neck round bottom flask (equipped with magnetic stir bar, thermometer, and addition funnel), charged diethoxyacetonitrile (111.1 g, 860 mmol) and methanol (620 mL, anhydrous) while under a steady nitrogen flow. Via an addition funnel, slowly charged 25 wt % solution of sodium methoxide (4.64 g, 86 mmol, 19.7 mL) in methanol. (Note: addition is slightly exothermic). The mixture was stirred for 15 h, at which point, the solvent was removed under vacuum (Note: starting material had not been completely converted according to NMR). The residue was dissolved in methanol and charged with a fresh sodium methoxide solution- same concentration/equivalents- and stirred another 15 h). The solvent was removed under vacuum and the residue was dissolved in diethyl ether (1.0 L), with the organic phase washed with water (3 x 500 mL), then brine (1 x 300 mL). The organic layer was dried over magnesium sulfate, the salts filtered and the solvent reduced under vacuum to give 89.9 g of a crude mixture of methyl 2,2-diethoxyethanimidoate and un-reacted starting material (10-12 mol % by NMR) as a thin oil. Note that best yields of the imidate are obtained when the organic layer is stripped of at 400 mbar and 45 0C because of its volatility.The oil was dissolved in methanol (300 mL,) and placed into a 2 L round bottom flask (equipped with magnetic stir bar, reflux condenser) along with 1-(4-bromophenyl)methanamine (100.0 g, 537 mmol) and the mixture subjected to heating in a pre-heated oil bath. The mixture was stirred at 700C for 18 h and then allowed to cool. The solvent was removed to give 158.8 g of the desired intermediate (1) in 93.8% yield (based on 1-(4-bromophenyl)methanamine as limiting reagent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6136-93-2, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/125405; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts