Author: Jessica.F

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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

Step 2. 3-Hydroxycyclobutane-l-carbonitrile. Sodium borohydride (597 mg, 15.8 mmol) was added in portions into a cold (0 C) mixture of 3-oxocyclobutane-l- carbonitrile (1.0 g, 10.52 mmol) and anhydrous methanol (10 mL). After the addition the mixture stirred for 30 minutes, and then it was carefully poured into ice water. The mixture was extracted with ethyl acetate and the organic extracts washed with water and brine and dried over anhydrous MsS04. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes: EtOAc 2/1 ratio) to afford 3- hydroxycyclobutane-l-carbonitrile, 8: 1 isomeric mixture, as oil (920 mg, 92% yield): XH NMR (500MHz, CDCh) delta ppm [4.62 (m), 4.26 (m), 1H], [3.06 (m), 2.75 (m), 2H], [5.65 (m), 2.33 (m), 2H], 2.6 (m, 1), 2.31 (m, 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); 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. 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-cyano-2-methylpropanoate

At -10C, hydrogen chloride gas was bubbled into an ethanol (50 ml) solution of 8.00 g of the mixture of cyano-dimethylacetic acid ethyl ester and cyano-dimethylacetic acid methyl ester (I-69), while stirring for 6 hours. After concentration of the reaction solution, ether was added to the thus obtained residue and stirred for 30 minutes, and the precipitated crystals were collected by filtration and dried to obtain 8.2 g of the title compound as a colorless solid. This was directly used in the subsequent reaction.

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); A1;,
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Electric Literature of 214623-57-1,Some common heterocyclic compound, 214623-57-1, name is 5-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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.

a 2-Methoxyl-5-N-[[4-morpholino]carbonyl]amino benzonitrile To a stirred mixture of 2-methoxyl-5-aminobenzonitrile (2 g, 12.34 mmol), and pyridine (1.28 g, 16.2 mmol) in dried CH2Cl2 (20 mL) was added 4-morpholinecarbonyl chloride (2.42 g, 16.2 mmol). After stirring at RT for 24 h, the mixture was diluted with CH2Cl2 and washed with H2O, brine, dried over MgSO4, concentrated to give an orange solid (3.04 g, 86%) 1H NMR: (400MHz, DMSO-d6): d 3.23 (t, J=4.9 Hz, 4H), 3.47 (t, J=4.9 Hz, 4H), 3.9 (s, 3H), 6.89 (d, J=9 Hz, 1H), 7.3 (d, J=9 Hz, 1H), 8.01 (s, 1H).

The synthetic route of 214623-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
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Related Products of 53312-78-0,Some common heterocyclic compound, 53312-78-0, name is 3-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

Representative of synthesis of ( N-(3-(3-aminopropanamido)-5-chlorobenzyl)-6 – chloro-1, 3, 4,9-tetrahydro-2H-pyrido[ 3, 4-b lindole-2-carboxamide : To a solution of 3-amino-5- chlorobenzonitrile (1.0 g, 6.55 mmol,1.0 eq), 3-((tert-butoxycarbonyl) amino) propanoic acid (1.24 g, 6.55 mmol,1.0 eq) and HATU (2.98 g, 7.86 mmol,1.2 eq) in DMF (15 mL) was added DIEA (2.5 g,19.65 mmol, 3.0 eq) at 25 C. Then the reaction mixture was stirred at 25 C for 1 hr. TLC showed 3 -amino-5 -chlorobenzonitrile was consumed completely and one new spot formed. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined organic phase was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: PE/EA = 5/1 to 3/1) to give tert-butyl (3 -((3- chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (1.5 g, yield: 70.8%) as a yellow solid. NMR (400 MHz, DMSO-^) d 10.42 (s,1 H), 7.98 (d, J = 1.6 Hz,1 H), 7.92 (s,1H), 7.71 -7.67 (m,1 H), 6.90 (t, J = 5.2 Hz,1 H), 3.32 (s, 2 H), 3.22 (dd, J = 12.8, 6.8 Hz, 2 H),1.37 (s, 9 H). [0234] To a solution of tert-butyl (3-((3-chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (500 mg,1.54 mmol,1.0 eq) in methanol (10.0 mL) was added Raney-Ni (180 mg, 3.08 mmol, 2.0 eq) and NH3·H20 (0.1 mL). The reaction was stirred at 25 C for 4 hrs under . LCMS showed the complete consumption of the starting material, and the desired product mass was detected. The reaction mixture was filtered and concentrated in vacuo to give tert-butyl (3- ((3-(aminomethyl)-5-chlorophenyl) amino)-3-oxopropyl) carbamate (460 mg, yield: 90.9%) as a yellow oil. LCMS: [M+H] + = 328.1

The synthetic route of 53312-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RECREO PHARMACEUTICALS LLC; ZHANG, Jing; WANG, Xiang; PODOLL, Jessica, D.; (207 pag.)WO2020/37155; (2020); 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Oxocyclobutanecarbonitrile

3,3-difluorocyclobutanecarbonitrile[1268] Example 125 A (8.21 g, 86 mmol) in dichloromethane (135 mL) was stirred at room temperature, cooled to <10 C, added DAST (1 1.41 mL, 86 mmol), warmed to room temperature, and stirred for 2 hours. The mixture was poured into saturated aqeuous NaHCC (200 mL) and partitioned. The aqueous phase was extracted with 2 x 50 mL dichloromethane. The combined organic phase was dried (Na2S04), filtered, and concentrated to give Example 125B (9.14 g, 78 mmol, 90 % yield) as a brown oil. XH NMR (400 MHz, CDC13) ? 3.06 - 2.91 (m, 5H). According to the analysis of related databases, 20249-16-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
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Application of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, 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.

A solution of 25.0 g (150 mmol) of 4- (hydroxymethyl) benzonitrile, 20.8 g (300 mmol) of hydroxyamine hydrochloride and 50.4 g (600 mmol) of sodium bicarbonate in 250 [ML] of methanol was heated to reflux and stirred for 20 h. The reaction mixture was cooled to rt and filtered. The solid was washed with 100 mL of methanol. The combined methanol solution was concentrated to dryness to afford [31.] 0 g (99 %) of the title compound: 1H NMR (400 Mhz, CD30D) [8] 4.63 (s, 2H), 7.39 (d, J= 8.0, 2H), 7.62 (d, J= 8.0, 2H).

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; WO2003/105771; (2003); A2;,
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Reference of 53312-81-5, 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 9: 5- 5-(Benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrileA suspension of 2-chloro-5-benzyloxypyrimidine (2.0g, 9.074mmol), 5-amino-2- fluorobenzonitrile (1.24g, 9.074mmol), in’5,(dibenzylideneacetone)palladium(0) (415 mg, 0.45mmol), 4,5-bi5,(diphenylphosphino)-9,9-dimethylxanthene (525 mg, 0.90 mol) and cesium carbonate (5.9g, 18.1mmol) in de-gassed 1,4-dioxane (15mL) was heated at 80 C for 2 days. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by flash chromatography, using 0-5% ethyl acetate:hexane as eluent, to give 5- [5- (benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrile (2.88g) as yellow solid.Mass: (ES+) 321(M+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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
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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. 14447-18-8, name is Benzyl cyanoacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Benzyl cyanoacetate

General procedure: A 100-mL round-bottom flask equipped with a stir bar is charged with dimethyl malonate (2.0 g, 15.0 mmol), crotonaldehyde (1.3 mL, 15.0 mmol), piperidine (0.2 mL, 3.0 mmol), benzoic acid (0.4 g, 3.0 mmol) and toluene (50 mL). The reaction mixture is heated at reflux using a Dean-Stark apparatus for 2 h. The toluene solution is washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel column chromatography eluting with hexanes/ethyl acetate (20/1) to afford 1a (1.7 g, 60% yield) as a red liquid.

The synthetic route of 14447-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wei; Ghiviriga, Ion; Grenning, Alexander J.; Tetrahedron; vol. 73; 29; (2017); p. 4076 – 4083;,
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Related Products of 29509-06-6,Some common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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 B22 To a stirring suspension of 6-aminobenzothiazole (0.500 g, 3.33 mmol) in cone. HCl (5 ml) at 0-5 C. was added a solution of NaNO2 (0.276 g, 3.99 mmol) in H2O (5 ml). The mixture was stirred at 0-5 C. for 75 min until a clear yellow solution was obtained. To this was then added a solution of SnCl2.2H2O (2.76 g, 13.3 mmol) in conc. HCl (5 ml). After completing the addition, the suspension was stirred at RT for 2 h. 4-Methyl-3-oxopentanenitrile (0.444 g, 3.99 mmol) and EtOH (50 ml) were added and the reaction was stirred with heating at 75 C. After 18 h, the completed reaction was cooled to RT and concentrated to an aqueous residue. This was chilled thoroughly in ice and made strongly basic (pH 12-13) by the addition of 6M NaOH. While still cold the mixture was extracted with EtOAc (2*). The combined organics were washed with H2O (2*), brine (1*), dried (MgSO4), filtered and evaporated to afford crude 1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine (0.8 g, 93% yield) as an oil which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6) delta 9.36 (s, 1H), 8.30 (d, J=2.4 Hz, 1H); 8.10 (d, J=8.8 Hz, 1H), 7.74 (dd, J=2.4 and 8.8 Hz, 1H), 5.36 (s, 1H), 5.33 (brs, 2H), 2.76 (septet, J=6.8 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 259.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-3-oxopentanenitrile, its application will become more common.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/90856; (2008); A1;,
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Reference of 20249-16-5, These common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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 73.2-(6-Fluoro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid [ 1 -(cis-3 – hydroxy-cyclobutyl)-ethyl]-amideStep 1cis-3-Hydroxy-cyclobutanecarbonitrile H3-Oxocyclobutanecarbonitrile was prepared according to Elend, D.; Fengas, D.; Fray, J. M. Synthetic Communications, 2005, 35, 657. To a solution of 3-oxocyclobutanecarbonitrile (600 mg, 6.31 mmol) in MeOH (25 mL) at 0C was slowly added sodium borohydride (263 mg, 6.94 mmol). The reaction mixture was stirred at 0C for 1 h then quenched with water and brine and extracted with EtOAc (3x). The combined organics were dried over MgSC^ and concentrated to afford 500 mg (82%) of cis-3 -hydro xy-cyclobutanecarbonitrile as a colorless oil. 1H NMR(CDCls, 300 MHz): ? (ppm) 4.26 (quin, J=7.5 Hz, 1H), 2.70 – 2.82 (m, 2H), 2.50 – 2.66 (m, 1H), 2.26 – 2.41 (m, 2H), 2.09 (br. s., 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
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