Category: nitriles-buliding-blocks

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. 33279-01-5, name is 3-Oxopentanenitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Oxopentanenitrile

Step: 1H- thieno[3,2-c] pyrazole-5-carbaldehyde (200mg, 1.314mmol) (see preparation step togetherPreparation Example 1 a) and 3-oxopentanenitrile (191mg, 1.972mmol) wasdissolved in dichloromethane together (20 mL), add The piperidine (11mg,0.131mmol), glacial acetic acid (12mg, 0.197mmol), under nitrogen at refluxovernight trans should. The filtered reaction mixture was cooled to roomtemperature, was added absolute ethanol (20 mL) was diluted reaction mixturewas stirred for ten minutes, filtered It was concentrated to dryness and theresidue was added ethyl acetate (5mL) and petroleum ether (10 mL), stirred forfive minutes and filtered, the solid Dried to give 2 – ((1H- thieno [3,2-c]pyrazol-5-yl) methyl-enyl) -3-oxo-valeronitrile (190mg, 62.5%). ESI-MS: 232 [M+ H].

The synthetic route of 33279-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Huilun life Science & Techonology Co.,Ltd; Cheng, Jianjun; Qin, Jihong; Ye, Bin; (68 pag.)CN103467481; (2016); B;,
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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. 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5ClFN

To a mixture of 3-chloro-2-fluoro-benzaldehyde (13.7 g, 86.68 mmol, 1.05 eq) and 2- (4-chloro-2-fluoro-phenyl)acetonitrile (14 g, 82.56 mmol, 1 eq) in methanol (200 mL) was added the solution of sodium methoxide (13.4 g, 247.67 mmol, 3 eq) in methanol (40 mL) dropwise at 0 C under nitrogen atmosphere. The product begins to precipitate during the addition. The suspension was stirred at 45 C for 5 hours. The solid was filtered and washed with water (200 mL) and methanol (50 mL) and then was dried in vacuum to give (Z)-3-(3-chloro-2-fluoro- phenyl)-2-(4-chloro-2-fluoro-phenyl)prop-2-enenitrile (24 g, 77.39 mmol, 93% yield) as a white solid. 1H-NMR (400MHz, CDCL) d 8.20 – 8.10 (m, 1H), 7.81 (s, 1H), 7.64 – 7.49 (m, 2H), 7.33 – 7.20 (m, 3H).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
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Some common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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. Formula: C7H3ClFN

To a solution of 2-chloro-4-fluoro-benzonitrile (4 g, 25.71 mmol) in DMF (20 mL) were added Na2S (3.01 g, 38.57 mmol). The mixture was held at room temperature with stirring on for 20 h. Then the mixture was added 1 M HCl to adjust to pH 6-7. MTBE (20 ml) and water (20 ml) was added. The aqueous phase was extracted with MTBE (20 mL X 2), the combined organic phases were washed with sat. NaHCC”3 (50 mL) and brine (50 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a yellow solid (3.7 g). The residue was used to next step directly. m/z calcd for [C7H4CINS]” [M-H]~: 168.0; found: 168.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60702-69-4, its application will become more common.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
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Application of 846023-24-3, The chemical industry reduces the impact on the environment during synthesis 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, I believe this compound will play a more active role in future production and life.

EXAMPLE 44 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.75 g, 6.75 mmol) in 8.2 mL of iso-propanol was added triethylorthoformate (1.5 g, 10.1 mmol). The mixture was heated to reflux. After 20 minutes, 4-methoxy-3-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenylamine in 20 mLs of iso-propanol was added dropwise so as to maintain reflux. After 26 hours, the reaction was cooled to room temperature and the suspended solids were filtered. The solids were rinsed with iso-propanol until effluent was colorless. The yellow solid was dried in vacuo to give 3.45 g (93%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide as a mixture of isomers. 1H NMR (300 MHz, CDCl3) delta 11.35 (br d, 1H), 8.17 (m, 2H), 7.76 (d, 1H), 7.41 (s, 1H), 6.88 (m, 1H) 6.69 (m, 2H), 4.10 (t, J=7 Hz, 2H), 3.96 (s, 3H), 3.87 (s, 3), 2.55 (t, J=7 Hz, 2H), 2.48 (m, 8H), 2.29 (s, 3H), 2.06 (m, 2H); MS (ES) m/z548.1 (M+) Analysis for C10H14ClNO2; Calcd: C, 55.69; H, 6.54; N, 6.49. Found: C, 55.49; H, 6.59; N, 6.32.

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-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); 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. 77-57-6, name is 1-Phenylcyclopentanecarbonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Phenylcyclopentanecarbonitrile

EXAMPLE 16 (R)-1-(2-((((1-Phenylcyclopent-1-yl)methylene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride To a solution of 1-phenyl-1-cyclopentanecarbonitrile (7.0 g, 41 mmol) in n-heptane (100 ml) cooled to -30 C. was dropwise added a 1M solution of diisobutylaluminium hydride in n-heptane (82 ml, 82 mmol). The mixture was stirred at -30 C. for 1 h and at 0 C. for 1 h. The mixture was diluted with diethylether (100 ml) and silica gel (60 g) was carefully added keeping the temperature below -30 C. The mixture was then allowed to warm to room temperature and then stirred for 20 h. After filtration the filtrate was washed with water (2*100 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 3.45 g of the crude 1-phenyl-1-cyclopentanecarboxaldehyde.

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; Novo Nordisk A/S; US5608069; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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 17823-40-4, Recommanded Product: 17823-40-4

A mixture of (1,2-dihydroacenaphthylen-5-yl)boronic acid (1.6 g, 8 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1.0 g, 3.9 mmol), Pd2(dba)3 (0.18 g, 0.20mmol), SPhos (0.16 g, 0.4 mmol), K3PO4 (2.0 g, 8.7 mmol) in toluene (50 mL) was degassed and heated at about 120 C for about 16 hours. After filtered off precipitate and washed with toluene, the filtrate was purified by flash column using eluents of hexane to hexane/dichloromethane (7:3). Removal of solvent give awhite solid (Compound 9) (0.54 g, in 42% yield).

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-Bromo-2,3,5,6-tetrafluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
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Synthetic Route of 69395-13-7, These common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, 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.

(ii) t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound. 1H NMR (300 MHz; CDCl3): delta7.4-7.8 (m, 5H), 7.10 (m, 1H), 6.63 (dd, 1H), 6.24 (s, 1H), 4.18 (t, 2H), 3.16 (t, 2H), 2.02 (s, 3H), 1.51 (s, 9H)

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astra Aktiebolag; US6221898; (2001); B1;,
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Reference of 60899-34-5, 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. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, 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.

(S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l-ylidene]-2-methylpropane-2- sulfinamide: To a solution of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in Toluene (60 mL) was added (S)-2-methylpropane-2-sulfinamide (4.24 g, 34.98 mmol, 1.10 equiv), Ti(OEt)4 (10.75 g, 47.15 mmol, 1.48 equiv). The resulting solution was stirred for 16 h at 60 C. The resulting solution was used directly in the next step without further purification. LC-MS: m/z = 261 [M+H]+. To a solution of l -oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in toluene (50 mL) was added (S)-2-methylpropane-2-sulfinamide (4.6 g, 37.95 mmol, 1.20 equiv), Ti(OEt)4 (1 1 g, 1.50 equiv). The resulting solution was stirred for 18 h at 60 C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of sat. potassium sodium tartrate (30 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 5.5 g (66%) of (S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l -ylidene]-2- methylpropane-2-sulfinamide as a yellow green solid. LC-MS: m/z = 261 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); 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. 691877-03-9, name is 3-Bromo-5-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)benzonitrile

43-2 (50 mg, 0.200 mmol) was dissolved in THE (1 mL) before 1M Borane in THF (1 ML) was added. The mixture was stirred at RT overnight before concentrated IN VACUO. The residue was redissolved in a solution of 1% HCl (4N in dioxane) in methanol and heated at 50 C overnight. Solvent was stripped off and redissolved in 1% HCl in methanol. This process was repeated three times to get ride of excess borane and yield crude 43-3 (50 mg, 98.4%). LC-MS: MW calculated 252.97, found 253.8.

According to the analysis of related databases, 691877-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/41279; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 90433-20-8, name is 2-(3-Bromophenyl)-2-methylpropanenitrile, 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 90433-20-8, Recommanded Product: 2-(3-Bromophenyl)-2-methylpropanenitrile

General procedure: To a mixture of compound 5 (2.00 g, 12.3 mmol), X-Phos (0.292 g, 0.613 mmol), sodium tert-butoxide (2.94 g, 30.6 mmol) and tris(dibenzylidineacetone)dipalladium (0.224 g, 0.245 mmol) in 1,4-dioxane (25 mL) was added 4-bromoanisole (1.6 mL, 12.9 mmol) and heated to 100 C for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo. The residue was powdered from diethyl ether to give the title compound (2.02 g, 61%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Bromophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Mochizuki, Michiyo; Kori, Masakuni; Kono, Mitsunori; Yano, Takahiko; Sako, Yuu; Tanaka, Maiko; Kanzaki, Naoyuki; Gyorkos, Albert C.; Corrette, Christopher P.; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4675 – 4691;,
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