Author: Jessica.F

191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, 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. Computed Properties of C8H6FNO

Pyrazolospiroketone Preparation 11; 2-Methoxy-4-(3′-methyl-7′-oxo-6′.7′-dihvdro-2’H-spirorpiperidine-4,5′-pyranor3.2-clPyrazol1-2′-; To a solution of 4-fluoro-2-methoxybenzonitrile (100 g, 0.662 mol) in ethanol (0.66 L) was added hydrazine monohydrate (331 g, 0.321 L, 6.62 mol). The mixture was heated at reflux overnight. The reaction was cooled to room temperature, diluted with water (750 mL), stirred for 1.5 hours and the resulting solids were collected by filtration. The solids were rinsed with water (2 x 250 mL) and air dried for 3 hours. The solids were then dried in a vacuum oven at 45 QC. The material was dissolved in dioxane (2 L) and HCI gas was bubbled through for 30 minutes. The resulting solids were filtered and washed with methyl tert-butyl ether (2 x 1 L). The solids were air dried for 1 hour and the resulting solids were dried in a vacuum oven at 45 QC to provide -hydrazino-2-methoxybenzonitrile hydrochloride (115.6 g, 87.5%).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER, INC.; WO2009/144554; (2009); 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. 41429-22-5, name is 2-(2-(Difluoromethoxy)phenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H7F2NO

[0607] To a solution of [2-(difluoromethoxy)phenyl]acetonitrile (5.00 g, 27.3 mmol) in THF (25 ml) under argon was added gradually while stirring, at -78C., a 2 M solution of LDA in THF (16 ml, 33 mmol). The mixture was allowed to come to 0C. and, after 15 min, cooled back down again to -78C. Subsequently, a solution of tert-butyl 3-bromopropanoate (5.2 ml, 33 mmol) in THF (10 ml) was slowly added dropwise thereto at -78C. while stirring. Stirring of the mixture was continued overnight, in the course of which the cooling bath (dry ice/acetone) was allowed to come gradually to RT. Subsequently, water and ethyl acetate (100 ml of each) were gradually added at about 0C. to the mixture, which was agitated. After phase separation, the aqueous phase was extracted once with ethyl acetate (100 ml). The combined organic phases were washed once with saturated aqueous sodium chloride solution (150 ml), dried over sodium sulfate, filtered and concentrated, and the residue was taken up in dichloromethane and purified by flash column chromatography (100 g silica gel Biotage Snap-Cartridge Ultra, cyclohexane/ethyl acetate gradient 93:7?7:3, Isolera One). The combined target fractions were concentrated and the residue was dried under reduced pressure. This gave 3.85 g (83% purity, 38% of theory) of the title compound. [0608] LC-MS (Method 1): Rt=2.10 min; MS (ESIpos): m/z=312 [M+H]+

The synthetic route of 41429-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengeseiisehaft; BECK, Hartmut; KAST, Raimund; MEININGHAUS, Mark; DIETZ, Lisa; FUERSTNER, Chantal; STELLFELD, Timo; ANLAUF, Sonja; VON BUEHLER, Clemens-Jeremias; BAIRLEIN, Michaela; ANLAHR, Johanna; MUENSTER, Uwe; TERJUNG, Carsten; JOERISSEN, Hannah; HAUFF, Peter; MUELLER, Joerg; DROEBNER, Karoline; NAGEL, Jens; (220 pag.)US2020/31775; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50635-21-7, name is o-Tolyloxyacetonitrile, 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 50635-21-7, Safety of o-Tolyloxyacetonitrile

Preparation example 19: 2-(2-Methylphenoxy)acetamidine The above-titled product was obtained in the same method as in Preparation example 7 using 2-(2-methylphenoxy)acetonitrile instead of 4-chlorophenoxy-acetonitrile. 1H-NMR (DMSO-d6) delta: 4.92(2H, s), 6.85(1H, d, J=8.5Hz), 6.91-6.96(1H,m),7.16-7.22(2H, m), 9.15(3H, brs). Mass (EI, m/z): 164(M+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1142881; (2001); A1;,
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Synthetic Route of 914250-82-1, 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 914250-82-1 as follows.

3-bromo-2-chlorobenzonitrile (500 mg, 2.30 mmol), bis(pinacolato)diboron (741 mg, 2.92 mmol), [l,l ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (93.9 mg, 115 muiotaetaomicron) and potassium acetate (689 mg, 7.03 mmol) were weighed into a 40 ml vial equipped with a teflon/rubber screw cap and a stir bar. The reaction vessel was purged 3 times with N2, dioxane (degassed) (18.4 mL) was added against N2 and the headspace of the reaction was purged 3 more times with N2. The reaction was placed into a heating block preheated to 85 C and stirred vigorously at this temperature for 2.5 hours. After cooling to room temperature the mixture was filtered over celite, the filtrate was evaporated to dryness and the crude product was purified by column chromatography (0 – 99% EtO Ac/heptanes) to give 370 mg (61%) of the desired product. LC-MS (ESI) m/z: [M + H] calculated for CI3HI5BC1N02: 264.10, found 263.8.

According to the analysis of related databases, 914250-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REVOLUTION MEDICINES, INC.; JOGALEKAR, Ash; WON, Walter; KOLTUN, Elena S.; GILL, Adrian; MELLEM, Kevin; AAY, Naing; BUCKL, Andreas; SEMKO, Christopher; KISS, Gert; (496 pag.)WO2018/13597; (2018); A1;,
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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 66389-80-8 as follows. category: nitriles-buliding-blocks

Synthesis of SiR-Tz (FIG. 8) (0148) 4-Cyanobenzylamine HCl was Boc-protected with Boc-anhydride. The Boc-protected amine was converted to the tetrazine 8 (Yang, et al., 2012, Angew. Chem., Int. Ed. 51:5222-5225). The Boc-group of tetrazine 8 was removed by treating the compound with a 1:1 mixture of TFA and dichloromethane and immediately coupled with SiR-OH (Lukinavicius, et al., 2013, Nature Chem. 5:132-139) mediated by TBTU and iPr2NEt.

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
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These common heterocyclic compound, 64113-85-5, name is 4-Methyl-[1,1′-biphenyl]-2-carbonitrile, 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. Formula: C14H11N

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

The synthetic route of 4-Methyl-[1,1′-biphenyl]-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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Adding a certain compound to certain chemical reactions, such as: 91132-15-9, name is 2-(4-(Hydroxymethyl)phenyl)-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 91132-15-9, Safety of 2-(4-(Hydroxymethyl)phenyl)-2-methylpropanenitrile

a- Synthesis of Int. 51 : To a suspension of 7 (2.5 g, 1 1 .3 mmol ), 2-[4-(hydroxymethyl)phenyl]-2- methylpropanenitrile (1.8 g, 10.3 mmol ), PPh3 supp (3.8 g, 12.3 mmol ) in d y DCM (50 mL) was added DBAD (2.8 g, 12.3 mmol) and the r.m. was stirred at r.t. for 18 h. The mixture was filtered through Celite, washed with DCM and the filtrate was evaporated until dryness. The residue (7g) was purified by prep. LC (irregular SiOH 35-40muiotaeta, 90g GraceResolv, gradient from 95% heptanes, 5% EtOAc to 80% heptanes, 20%> EtOAc). The fractions were collected and evaporated until dryness to give 2. lg of Int. 51 (54%).

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-(4-(Hydroxymethyl)phenyl)-2-methylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Reference of 1211596-75-6, 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 1211596-75-6 as follows.

Step 4: 2-(Hydroxymethyl)-6-(trifluoromethyl)benzonitrile To a solution of LiBH4 (3.3 g, 153 mmol) in THF (100 mL) was added methyl 2-cyano-3- (trifluoromethyl)benzoate (14 g, 61 mmol). The mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo to give the crude product, which was diluted with water, and extracted with EtOAc. The organic layer was separated, dried over Na2S04, filtered, and concentrated to give the crude product 2-(hydroxymethyl)-6- (trifluoromethyl)benzonitrile (10 g, 77% yield): 1H NMR (400 MHz, CDC13) delta 7.83-7.72 (m, 3H), 5.46 (s, 2H); ES-LCMS m/z 202.1 (M+H).

According to the analysis of related databases, 1211596-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; KEENAN, Richard, M.; MILLER, Aaron, Bayne; QIN, Donghui; WO2013/177349; (2013); A2;,
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Adding a certain compound to certain chemical reactions, such as: 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile, 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 4421-09-4, Computed Properties of C8H5NO2

5-(1,3-benzodioxol-5-yl)-1H-tetrazole was synthesized from 1,3-benzodioxole-5-carbonitrile by following a reported procedure [46]. The requisite nitrile (2) was prepared from Piperonal (1,3-benzodioxole-5-carbaldehyde) via oxime formation, followed by dehydration with acetic anhydride, following a reported procedure [45]. Nitrile (2.95 g, 20 mmol), sodium azide (1.43 g, 22 mmol) and zinc bromide (4.50 g, 20 mmol), were put in 60 mL of water. 5 mL of isopropanol was also added to stop the formation of clumps. The reaction mixture was refluxed for 24 h and monitored by TLC; vigorous stirring is essential. After 24 h HCl (3 N, 30 mL) and ethyl acetate (100 mL) were added, and vigorous stirring was continued until no solid was present and the aqueous layer had a pH of 1. If necessary, additional ethyl acetate was added. The organic layer was isolated and the aqueous layer extracted with 2 × 100 mL of ethyl acetate. The combined organic layers were evaporated, 200 mL of 0.25 N NaOH was added, and the mixture was stirred for 30 min, until the original precipitate was dissolved and a suspension of zinc hydroxide was formed. The suspension was filtered, and the solid washed with 20 mL of 1 N NaOH. To the filtrate was added 50 mL of 3 N HCl with vigorous stirring causing the tetrazole to precipitate. The tetrazole was filtered and washed with 2 × 50 mL of 3 N HCl and dried in a drying oven to furnish the tetrazole as a white powder.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Wani, Mohmmad Younus; Bhat, Abdul Roouf; Azam, Amir; Choi, Inho; Athar, Fareeda; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 313 – 320;,
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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. 53312-78-0, name is 3-Amino-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Amino-5-chlorobenzonitrile

A mixture of 3-amino-5-chloro-benzonitrile (2.4 g, 15.7 mmol), 4-chloro-2-methyl- benzaldehyde (2.4 g, 15.7 mmol) and 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (2.9 g, 15.7 mmol) in acetic acid (15 mL) was stirred at 120C for 16 h. The reaction mixture was allowed to cool to rt, concentrated, diluted with acetonitrile (15 mL), and stirred for 4 h at rt The resulting precipitate was collected by vacuum filtration and dried to afford 1.8 g of the title compound. tR: 6.50 min (HPLC 2); ESI-MS: 429 [M+H]+(LC-MS 2); Rf= 0.27(hexane/EtOAc, 1 :1 ).

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

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; MAH, Robert; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/80141; (2013); A1;,
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