Tag: M.W=100-200

Some common heterocyclic compound, 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 2-Fluoro-4-nitrobenzonitrile

Methyl 3-amino-6-nitrobenzothiophene-2-carboxylate: Methyl thioglycolate (0.08 mL, 0.85 mmol) was added to a solution of 2-fluoro-4-nitrobenzonitrile (145 mg, 0.87 mmol), and triethylamine (0.14 mL, 1.0 mmol) in acetonitrile (20 mL) stirred under nitrogen at 25° C. After 3 hours further triethylamine (0.28 mL, 2.0 mmol) was added to the solution, which was stirred at 25° C. for a further 16 hours. The solvent was removed under reduced pressure to give a brown residue, which upon trituration with chloroform precipitated methyl 3-amino-6-nitrobenzothiophene-2-carboxylate (103 mg, 54percent) as a red brown solid, mp 228.5-229.5° C. 1H NMR (DMSO-d6): delta 8.87 (d, J=2.0 Hz, 1H), 8.32 (d, J=9.0 Hz, 1H), 8.15 (dd, J=8.8, 2.0 Hz, 1H), 7.26 (brs, 2H), 3.77 (s, 3H). Mass Spectrum (CI): 253 (100, MH+), 252 (52, M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34667-88-4, its application will become more common.

Reference:
Patent; Warner-Lambert Company; US6344459; (2002); B1;,
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Reference of 123-06-8, The chemical industry reduces the impact on the environment during synthesis 123-06-8, name is Ethoxymethylenemalononitrile, I believe this compound will play a more active role in future production and life.

3.2 5-Amino-4-cyano-1-phenyl-1H-pyrazole (3a) A solution of phenylhydrazine (2d) (0.45 mL, 4.2 mmol) and ethoxymethylenemalononitrile (1b) (0.51 g, 4.2 mmol) in EtOH (4 mL) was irradiated at 120 C for 45 min in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (100 W). After cooling in a flow of compressed air, the solvent was evaporated in vacuo. Purification by column chromatography on silica, eluting with light petroleum/EtOAc (5:1 v/v), gave the title compound (0.738 g, 95%) as a light brown solid, mp 137-139 C (lit. 29 mp 137 C) (found: 185.0827. C10H9N4 [MH] requires 185.0822); FTIR (KBr)/cm-1 numax 3302 (NH), 3240 (NH), 2230 (CN), 1577, 1530, 1368; 1H NMR (400 MHz; CDCl3) delta 7.58 (1H, s, H-3), 7.49-7.37 (5H, Ph), 4.52 (2H, br s, exch. D2O, NH2); 13C NMR (100 MHz, CDCl3) delta 141.9 (CH), 135 (C), 129.3 (C), 125.5 (CH), 124.1 (CH), 121.3 (CH), 115.6 (C), 86.2 (C); LRMS (APcI) m/z (rel intensity) 226 ([M+MeCNH]+, 100), 185 (MH+, 64).

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, Ethoxymethylenemalononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bagley, Mark C.; Baashen, Mohammed; Paddock, Victoria L.; Kipling, David; Davis, Terence; Tetrahedron; vol. 69; 39; (2013); p. 8429 – 8438;,
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Electric Literature of 7251-09-4, 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. 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 6-chloro-7-hydroxy-2-oxo-l,2-dihydroquinoline-3- carbaldehyde (58.0 mg, 0.259 mmol) and 4-amino-2-methoxybenzonitrile (48.0 mg, 0.324 mmol) in DCM (4.0 mL) was treated with acetic acid (0.07 mL, 1.223 mmol) and stirred 10 minutes. Sodium triacetoxyborohydride (84.0 mg, 0.396 mmol) was added. The mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with water (2×50 mL) and brine (50 mL), dried (Na2S04), filtered, and evaporated under reduced pressure. The residue was dissolved in methanol, treated with silica gel, and evaporated. The material was chromatographed by Biotage MPLC (10 g silica gel column) with 20 to 100% EtOAc in hexanes to provide the title compound 1-57 (18.6 mg, 0.052 mmol, 20.2 % yield) as a peach-coloured solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 11.82 (s, 1 H), 10.89 (s, 1 H), 7.70 (s, 1 H), 7.63 (s, 1 H), 7.28 (d, J=8.50 Hz, 1 H), 7.12 (dd, J=6.00, 6.00 Hz, 1 H), 6.91 (s, 1 H), 6.32 (d, J=1.76 Hz, 1 H), 6.22 (dd, J=8.60, 1.60 Hz, 1 H), 4.17 (d, J=5.60 Hz, 2 H), 3.78 (s, 3 H). LCMS (Method 4): Rt 1.17 min., m/z 356.1 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
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These common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, 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. SDS of cas: 21524-39-0

A mixture of 3 -methyl- lH-pyrazole-4-carboxylic acid ethyl ester (1.25 g, 8.1 1 mmol), potassium carbonate (1.68 g, 12.16 mmol), 2,3-difluorobenzonitrile (1.08 mL, 9.73 mmol) in dimethylformamide (12 mL) is heated at 100C with the aid of a magnetic stirred. After 2.5 hr. the reaction mixture is treated with water and extracted with ethyl acetate. The organic layer is decanted, washed with brine, dried over magnesium sulfate and the solvent evaporated under reduced pressure to give 2.3 g of l-(2-cyano-6-fluoro- phenyl)-3 -methyl- lH-pyrazole-4-carboxylic acid ethyl ester (this compound is contaminated with the other pyrazole regioisomer in a ratio 75:25). MS (m/z): 274 (M+1). A capped vial is charged with ethyl l-(2-cyano-6-fluoro-phenyl)-3-methyl- pyrazole-4-carboxylate (1.97 g, 7.21 mmol) (contaminated with the other pyrazole regioisomer in a ratio of 75:25, 1,2-ethanediamine, N-methyl- (6 mL, 68.02 mmol) and phosphorus pentasulfide (229 mg, 1,01 mmol) and the mixture is stirred at 1 10C for 30 min and then allow to reach rt. Solvent is evaporated in vacuo and the residue purified by normal phase Isco chromatography using dichloromethane/2M ammonia in methanol from 95/5 to 85/15 as eluent to yield 2.1 1 g of ethyl l-[2-fluoro-6-(l-methyl-4,5- dihydroimidazol-2-yl)phenyl]-3-methyl-pyrazole-4-carboxylate (contaminated with the other pyrazole regioisomer in a ratio 75:25). MS (m/z): 331 (M+1).

The synthetic route of 2,3-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; BENITO COLLADO, Ana Belen; DIAZ BUEZO, Nuria; JIMENEZ-AGUADO, Alma Maria; LAFUENTE BLANCO, Celia; MARTINEZ-GRAU, Maria Angeles; PEDREGAL-TERCERO, Concepcion; TOLEDO ESCRIBANO, Miguel Angel; WO2011/60217; (2011); A1;,
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Related Products of 145689-34-5,Some common heterocyclic compound, 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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.

(35′,5^-3-Amino-5-(23-difluorophenyl)-l-(2,2,2-trifluoroethyl piperidin-2-one hydrochloride; Step A: Ethyl 4-cvano-4-f2,3-difluorophenyl)butanoate; To a mixture of (2,3-difluorophenyl)acetonitrile (40.5 g, 265 mmol), ethyl acrylate (24 mL, 221 mmol), and hydroquinone (50 mg, 0.45 mmol) was added OH (2 M in MeOH, 2.0 mL, 4.0 mmol) and the resulting mixture was heated at 160 C for 16 h and then allowed to cool to ambient temperature. The crude mixture was purified by silica gel chromatography, eluting with a gradient of hexanes: EtOAc – 100:0 to 50:50, to give the title compound. MS: miz = 207.9 (M – OEt).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2,3-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; BELARDI, Justin; WO2012/129013; (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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

General procedure: To a solution of potassium tert-butoxide (8.0 g, 0.08 mmol,2.5 equiv) in THF (25 ml) at 30 C was added a solution of methyliodide (5.35 ml, 0.09 mmol, 3.0 equiv) and methyl 4-(cyanomethyl)benzoate (5.0 g, 0.03 mmol,1.0 equiv) in THF (25 ml) under nitrogen atmosphere over 20 min. The cooling bath was removed and the reaction mixture was allowed to warm to rt and stirred for 2 h.Following this the reaction was quenched with water (10 ml) and ethyl acetate was added and the organic and aqueous layers were separated. The organic layer was washed with water, brine, anddried over sodium sulfate. The organic solvent was removed under vacuum to obtain a violet residue that was purified by column chromatography using 20:80 EtOAc:Pet ether to obtain an off white solid that was crystallized in CHCl3:Pet ether to afford the title compound (4.0 g, 69%) as a white solid.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kadam, Kishorkumar S.; Jadhav, Ravindra D.; Kandre, Shivaji; Guha, Tandra; Reddy, M. Mahesh Kumar; Brahma, Manoja K.; Deshmukh, Nitin J.; Dixit, Amol; Doshi, Lalit; Srinivasan, Shaila; Devle, Jayendra; Damre, Anagha; Nemmani, Kumar V. S.; Gupte, Amol; Sharma, Rajiv; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 337 – 347;,
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Related Products of 143879-77-0, 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. 143879-77-0, name is 2,6-Difluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

a) 2-Amino-6-fluoro-3-nitrobenzonitrileA solution of NH3 in EtOH (19 mL, 8.6 M, 160 mmol) was added dropwise to a solution of 2,6-difluoro-3-nitrobenzonitrile (10 g, 54 mmol) in THF (50 mL) at 0 C under Ar and the resulting mixture was stirred at 0 C for 1 h. The mixture was concentrated and the residue washed with brine and extracted with EtOAc. The organic layer was dried over Na2S04, filtered and concentrated.Yield: 9.59 g (98%).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; KUELZER, Raimund; MACK, Juergen; PFAU, Roland; STENKAMP, Dirk; PELCMAN, Benjamin; ROENN, Robert; LUBRIKS, Dimitrijs; SUNA, Edgars; WO2012/76672; (2012); A1;,
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Application 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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3759-28-2, name is 2-(Cyanomethyl)benzonitrile, 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. COA of Formula: C9H6N2

General procedure: To a solution of homophthalonitrile 2 (129 mg, 0.82 mmol) in PriOH (4 ml), salicylaldehyde 1 (2.46 mmol) and NH4OAc (143 mg, 1.64 mmol) were added. The mixture was placed into a microwave reactor and heated at 150 C for 10 min. The vessel was opened, MeNO2 (0.439 ml, 8.2 mmol) and Et3N (0.114 ml, 0.82 mmol) were added, the mixture was heated again in the microwave reactor at 150 C for 10 min. The solvent was evaporated under reduced pressure, the residue was chromatographed on silica gel (EtOAc-hexane, 1:5-1:1) (method A) or was dissolved in asmall volume of Et2O or CH2Cl2 and extracted with HCl aqueous solution(0.6 m, 3 30 ml). The aqueous layer was neutralized with Na2CO3. The precipitate was filtered off and washed with H2O several times and once with a small amount (1.5 ml) of PriOH and dried in air (method B).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Festa, Alexey A.; Storozhenko, Olga A.; Bella Ndoutoume, Delphine R.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Mendeleev Communications; vol. 27; 5; (2017); p. 451 – 453;,
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Adding a certain compound to certain chemical reactions, such as: 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, 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 327-74-2, Recommanded Product: 327-74-2

Intermediate I-IX-6 (I-19): 4-iodo-3-(trifluoromethyl)benzonitrile To a slurry of 4-amino-3-(trifluoromethyl)benzonitrile (5.48 g; 29.5 mmol) in HBF4 (50 mL; 48%) at -10 C. was added NaNO2 (2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 7.83 (dd, J=8.1, 1.6 Hz, 1H), 8.27 (d, J=1.5 Hz, 1H), 8.37 (d, J=8.1 Hz, 1H). Note 1 Solid was not allowed to dry completely on the filter.

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-Amino-5-cyanobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); A1;,
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