Month: July 2021

Synthetic Route of 2973-50-4, 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. 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 6-(difluoromethyl) pyridazine-4-carboxylic acid Int-29 (1 g, 5.75 mmol) in ethylacetate (60 mE) was added 2-(2-aminophenyl)acetoni- trile (759 mg, 5.75 mmol) andtriethylamine (1.6 mE, 11.49 mmol) at room temperature under an inert atmosphere. To this was added propylphosphonic anhydride (50% in EtOAc, 9.14 mE, 14.37 mmol) drop wise at 00 C. The reaction mixture was gradually warmed to room temperature and stirred for 2 h. After consumption of starting material (by TEC), the reaction mixture was basified using saturated sodium bicarbonate solution to pH .-8 and extracted with EtOAc (2×50 mE). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was triturated with n-pentane (2×25 mE) and dried under vacuum to afford N-(2-(cyanomethyl)phenyl)-6-(difluoromethyl)pyridazine- 4-carboxamide (1.4 g, 4.86 mmol, 85%) as a yellow solid.11619] ?H NMR (500 MHz, DMSO-d5): oe 10.77 (s, 1H),9.80 (s, 1H), 8.45 (s, 1H), 7.54-7.49 (m, 1H), 7.45-7.30 (m, 4H), 4.02 (s, 2H)11620] EC-MS: mlz 288.9 [M+H] at 2.25 RT (98.33% purity)

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-(2-Aminophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
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Application of 621-50-1,Some common heterocyclic compound, 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.

N-[3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-phenyl]-methanesulfonamide hydrochloride 1-Chloromethyl-3-nitro-benzene (5 g) and 4.28 g of sodium cyanide were dissolved in a mixture of 15 ml of water and 50 ml of dioxane and the two phase mixture was heated to 100C for 12 hr. The dioxane was removed by evaporation and the aqueous solution was extracted with dichloromethane. The organic extract was washed with brine, dried, and evaporated. The residue was purified by flash column chromatography eluding with EtOAc:hexane (1:4) to afford 2.86 g of a tan solid, mp 51.7-52.7C, of (3-nitro-phenyl)-acetonitrile. (3-Nitro-phenyl)-acetonitrile (2.79g) was dissolved in 50 ml of ethyl acetate and the mixture was treated with 19.5 g of tin (II) chloride dihydrate and stirred at room temperature for 72 hr. The mixture was diluted with ethyl acetate and treated with saturated sodium bicarbonate solution, separated, and extracted with ethyl acetate. The extracts were combined, dried, and evaporated, leaving 2.1 g of tan oil of (3-amino-phenyl)-acetonitrile.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; EP887346; (1998); A2;,
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Application of 26391-06-0, 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. 26391-06-0, name is 2-Cyano-N,N-diethylacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of arylaldehyde (1 equiv), 2-cyanoacetamide or derivative (1.0-1.5 equiv) and N-methylpiperazine (0.05-1.05 equiv) in methanol (2-10 ml) was stirred at room temperature overnight. After addition of an equivalent volume of water/methanol (1:1) or 1 N HCl/methanol (1:1) for acidic products, the precipitate was collected by filtration and washed with water/methanol (1:1). If precipitation did not occur, the mixture was evaporated and the residue was purified by flash chromatography.

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

Reference:
Article; Nitsche, Christoph; Steuer, Christian; Klein, Christian D.; Bioorganic and Medicinal Chemistry; vol. 19; 24; (2011); p. 7318 – 7337;,
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5332-06-9, name is 4-Bromobutanenitrile, 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. SDS of cas: 5332-06-9

Example 10; 4-Azidobutanenitrile (22).; Sodium azide (1.2 g, 18.5 mmol) was added to a solution of 4-bromobutyronitrile (20, 1.8 g, 12.0 mmol) in DMSO (20 mL). After 18 h of stirring at room temperature, water (40 mL) was added, and the solution was extracted with diethyl ether. Evaporation of the solvent gave 22 as a light yellow oil EPO (0.9 g, 67%). IH NMR (400 MHz, CDCl3) £3.5 (t, 2H, J= 6.0 Hz), 2.5 (t, 2H, J= 7.2 Hz), 1.90 – 1.95 (m, 2H).

The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2007/35964; (2007); A2;,
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Application of 34403-48-0, A common heterocyclic compound, 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, molecular formula is C9H10N2, 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.

Compound 489 5-(chloromethyl)-6-phenylimidazo[1,5-a]pyridine 55b (25 mg, 0.103 mmol), 491 4-((methylamino)methyl)benzonitrile (29 mg, 0.2 mmol), 27 K2CO3 (69 mg, 0.5 mmol) and 149 acetonitrile (5 mL) were mixed at room temperature, heated to 55 C. and stirred for 18 h. After cooled to room temperature, the mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1 to 1/3) to give the target 492 product 4-((methyl((6-phenylimidazo[1,5-a]pyridin-5-yl)methyl)amino)methyl)benzonitrile 55 (25 mg, light yellow oil). Yield: 71%.MS m/z (ESI): 353[M+1]1H NMR (400 MHz, CDCl3) delta 8.64 (s, 1H), 7.64-7.42 (m, 7H), 7.38-7.22 (m, 4H), 6.70 (d, J=9.2 Hz, 1H), 3.89 (s, 2H), 3.44 (s, 2H), 2.11 (s, 3H).

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Innocare Pharma Tech Co., Ltd.; CHEN, Xiangyang; GAO, Yingxiang; US2019/185472; (2019); A1;,
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623-26-7, name is Terephthalonitrile, 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. Recommanded Product: Terephthalonitrile

Example 38 Terephthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130 C. for six hours. The reaction mixture was cooled, and water (9 g) was added thereto. Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 30% and a selectivity of 96%.

The synthetic route of 623-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-2-fluorobenzonitrile

General procedure: A solution of quinolin-5-amine(7, 250 mg, 1.73 mmol) and TEA (200 L, 2.03 mmol) dissolved in CH2Cl2 (DCM, 15 mL) wasslowly dripped into a stirred solution of triphosgene (BTC, 256 mg, 0.85 mmol) in DCM (10 mL)by using a constant-pressure dropping funnel. Then, the mixture was stirred for another 0.5 h at room temperature (RT). After evaporation of the solvent, the residue was taken up in DCM (30 mL),and (5-(2,5-dichlorophenyl)furan-2-yl)methanamine (5b, 230 mg, 0.95 mmol) was added directly to the residue. The reaction mixture was stirred at RT for 6 h, and the solvent was subsequently removed in vacuo. The residue obtained was purified by column chromatography (V(PE):V(EA) = 1:1) to give the desired target compound 12 (343 mg, 0.84 mmol) in 88% yield. 96.8% HPLC purity.

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 53312-80-4.

Reference:
Article; Wang, Lijiao; Li, Chao; Chen, Wei; Song, Chen; Zhang, Xing; Yang, Fan; Wang, Chen; Zhang, Yuanyuan; Qian, Shan; Wang, Zhouyu; Yang, Lingling; Molecules; vol. 24; 15; (2019);,
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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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 499983-13-0

EXAMPLE 3Preparation of ethyl 3-fluoro-4-bromo-phenylacetate from 3-fluoro-4-bromo-phenylacetonitrile2.5 g of 3-fluoro-4-bromo-phenylacetonitrile, 4.7 g. of ethyl alcohol and 4.7 g of sulfuric acid were loaded at room temperature in an reactor. The mixture was heated to 100 C and stirred for 5 hours. When the conversion was completed, the mixture was cooled to room temperature, water and ethyl acetate were added and the aqueous phase was re-extracted with fresh ethyl acetate. The organic phase was washed with a sodium bicarbonate/water solution, then with water until pH=7. The organic phase was concentrated to yield 2.6 g, of crude product.

The synthetic route of 499983-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A; VERZINI, Massimo; Cotarca, Livius; Guidi, Alberto; Melloni, Alfonso; Maragni, Paolo; US2014/378696; (2014); A1;,
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These common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, 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: 19472-74-3

To a stirred solution of (2-bromophenyl)-acetonitrile (13) (5 g, 25.51 mmol) in a mixture of toluene and ethanol (1:1, 150 mL) was added 2-chloro phenyl boronic acid (14) (6 g, 38.2 mmol) and Na2CO3 (8.1 g, 76.53 mmol) at room temperature. Purging was conducting for 30 min with nitrogen. Then triphenyl phosphine (2.6 g, 10.2 mmol) was added followed by Pd(OAc)2 (0.287 g, 1.27 mmol) and further degassing was conducted for another 10 min. The reaction mixture was heated to reflux for 10 h. After completion of the reaction, the mixture was concentrated under reduced pressure to get a crude product which was purified using a silica column using 2% ethyl acetate in hexane to get (2?-chloro-biphenyl-2-yl)-acetonitrile (15) (4.9 g, 84.36%) as a yellow liquid.

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

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); 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 14618-78-1 as follows. name: 4,4-Dimethoxybutanenitrile

General procedure: One equiv. of carbazate was suspended in EtOH containing 10% (by vol.) of water(approx. 5 ml per mmol of the carbazate) and 1.05 equiv. of the acetal or ketal wasadded, followed by the addition of 0.05 equiv. of TFA. The reaction mixture was heatedto reflux and the progress of the reaction was monitored by TLC (thin layer chromatographyon silica gel) using ethyl acetate or a mixture of ethyl acetate-light petroleummixture (for the correct eluent, see characterization data of the compounds). After thereaction was complete, the reaction mixture was cooled to about 45C and three (3)equiv. of acetic acid was added, followed by the dropwise addition of a THF solutionof three (3) equiv. of NaBH3CN (approx. 1 ml of THF per 1.5 mmol of NaBH3CN).The reaction mixture was stirred at approx. 45C for 80 min. Subsequently, the reactionmixture was cooled to room temperature, acidified using 0.5 M HCl aqueous solution(6 ml of 0.5 M HCl per 1 mmol of starting carbazate) and stirred until the liberation ofhydrogen ceased. The reaction mixture was neutralized (to pH 8) by the dropwise additionof a saturated NaHCO3 solution (4 ml per 1 mmol of carbazate). The volatileswere removed under reduced pressure at approx. 40C. The residue was dissolved inethyl acetate, washed with saturated NaHCO3, twice with water and finally with saturatedaqueous sodium chloride. The combined aqueous washes were extracted twicewith ethyl acetate (25 ml per 1 mmol of expected product) and the extracts werewashed with saturated aqueous sodium chloride and combined with the organic phase. After drying over anhydrous Na2SO4 and evaporation of the solvent under reduced pressure,the residue was purified by column chromatography on silica gel using ethyl acetate-light petroleum (1:1 or 1:2) or ethyl acetate as eluent. For specific informationabout the eluent used to monitor the progress of the reaction and for purification, seethe Rf data for each compound.

According to the analysis of related databases, 14618-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 47; 6; (2015); p. 490 – 498;,
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