Author: Jessica.F

Application of 149793-69-1,Some common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Step l[0158] To a solution of 5-fluoro-3-(trifluoromethyl)benzenecarbonitrile (15.0 g, 79.3 mmol) in ethanol (30 ml) was added a solution of 50% hydroxylamine in water (10 ml, 151.5 mmol), and the resulting mixture was heated at 800C for 2 hours. The mixture was cooled to room temperature, solvent removed under reduced pressure, and 30 ml of water added. The suspension was sonicated and the solid filtered off, washed with water (2 x 20 ml), and dried under reduced pressure, to provide [5-fluoro-3- (trifluoromethyl)-phenyl](hydroxyimino)methylamine as a white solid. MS 223.1 (M+H).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV THERAPEUTICS, INC.; WO2009/94028; (2009); 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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 194853-86-6

3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol), 2-trifluoromethyl-4-fluorobenzonitrile (0.60 g, 3.3 mmol), DMSO 6 ml, 140 Heated at for 12h.Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid and stir for 0.5h.A white solid was obtained by suction filtration and purified by column chromatography to obtain a white solid with a yield of 92%.

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Tech University; Tao Youtian; Cao Xudong; Hu Jia; Huang Wei; (9 pag.)CN105037247; (2019); B;,
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Application of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 343; 1-(1-{2-[4-(Benzothiazol-2-yloxy)-phenyl]-ethyl}-piperazine-4-yl)-3-cyano-2- phenyl-isourea; The 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE hydrochloride was prepared from (1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}- piperidin-4-yl)-carbamic acid tert-butyl ester EXAMPLE 337 by removal of the Boc group according to EXAMPLE 266, step B. The free base was prepared by suspending 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE hydrochloride (1.3 g, 3.3 MMOL) in CH2CI2 (20 mL) and washing with a solution of saturated NaHCO3 (20 mL). The organic layer was dried over NA2SO4, filtered and concentrated under reduced pressure to give 1.0 g (83% yield) of 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE free base. A solution of 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YL AMINE (145 mg, 0.4 MMOL) in ethanol (5 mL) was treated with diphenyl cyanocarbodiimidate (319 mg. 1.34 MMOL) and heated to 80 C for 16h. The reaction was concentrated under reduced pressure and purified on Si02 (12 g, 0-10% [2 M NH3 CH30H]/CH2CI2) to give of the title compound (173 mg, 85% yield). MS (ESI) : exact mass calculated FOR C28H27N502S1, 496.2 ; m/z found, 498.4 [M+H].. H NMR (400 MHz, CDC13) : 7.73 (d, J = 8.7, 1 H), 7.66 (dd, J = 7.9, 0.7, 1 H), 7.45-7. 36 (m, 4H), 7.31-7. 24 (m, 5H), 7.08 (d, J = 7.8, 2H), 6.36 (br d, J = 6.5, 1 H), 3. 87-3. 76 (m, 1 H), 3.02 (br d, J = 11. 2, 2H), 2.83 (dd, J = 8.4, 7.3, 2H), 2.64 (DD, J = 8. 6,5. 4, 2H), 2.21 (t, J = 11. 1, 2H), 2.07 (d, J = 11.0, 2H), 1.76 (dd, J = 20.7, 10.4, 2H)

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, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/12296; (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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 36282-26-5

Example 4; 3-bromo-4-cyanophenylhydrazine; In a clean, dry 250-mL round-bottom flask, 2-bromo-4-fluorobenzonitrile (25.34 g) was dissolved in tetrahydrofuran (50 mL) under N2. To this was slowly added anhydrous hydrazine (50 mL). The solution color changed from yellow to red-orange. The reaction was allowed to stir at room temperature for 16 hours. A yellow-white crystalline solid precipitated from the solution. The mixture was then diluted with THF (50 mL) to dissolve the solids. The organic layer was then washed with saturated sodium bicarbonate solution until the pH of the organic layer was approximately 8.5. The organic layer was isolated and the solvent was removed under reduced pressure to give a white solid. This was place in a fritted glass funnel and washed with 1.5 L of water, followed by of diethyl ether (ca. 200 mL). The ether wash was then combined with the white solid and dried under reduced pressure. The title compound was isolated as a fluffy, white or off-white solid (23.43 g, 87.20% yield). MS m/z: calculated=212.05; m/z observed=252.98 (M+41).

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; Huang, Kenneth He; Eaves, Jeron; Veal, James; Hall, Steven E.; Barta, Thomas E.; Hanson, Gunnar J.; US2007/207984; (2007); A1;,
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Related Products of 19472-74-3, A common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

Step 1. A mixture of commercially available 2-bromophenylacetonitrile (10 g, 51 mmol) and tetrabutylammonium hydrogen sulfate (1.77 g, 5.1 mmol) in 60 mL of THF and 90 mL of 50% aqueous NaOH solution is heated at reflux for 10 min. Thereafter N-benzyl-N,N-bis(2-chloroethyl)amine hydrochloride (15 g, 56.1 mmol) are added at r.t. and the mixture is refluxed overnight. Cooling to r.t. is followed by dilution with water (120 mL) and extraction with EtOAc (2 x 200 mL). The combined organic extracts are washed with brine (100mL), dried with MgS04, and concentrated in vacuo. The crude compound is crystallized in acetonitrile to give 1-benzyl-4-(2-bromophenyl)piperidine-4-carbonitrile (12.6 g, 69% yield) as white crystalline solid. 1H NMR (500 MHz, DMSO D6) <5: 7.75 (dd, Ji = 1.3 Hz, J2 = 7.9 Hz, 1 H), 7.55 (dd, Ji = 1.6 Hz, J2 = 8.1 Hz, 1 H), 7.48 (td, Ji = 1.3 Hz, J2 = 7.4 Hz, 1 H), 7.35-7.32 (m, 5 H), 7.30-7.25 (m, 1 H), 3.58 (s, 2 H), 3.01-2.98 (m, 1 H), 2.98-2.95 (m, 1 H), 2.54-2.52 (m, 2H), 2.43-2.39 (m, 2 H), 2.00 (td, Ji = 3.4 Hz, J2 = 12.8 Hz, 2 H). 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; IDORSIA PHARMACEUTICALS LTD; BOLLI, Martin; BROTSCHI, Christine; LESCOP, Cyrille; WILLIAMS, Jodi T.; (0 pag.)WO2019/234115; (2019); A1;,
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Electric Literature of 57381-51-8, 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

b 4-Chloro-2-{[3-(Methylamino)-1-Phenylpropyl]Thio]Benzonitrile Hydrochloride [3-(Acetylthio)-3-phenylpropyl]methylcarbamic acid 1,1-dimethylethyl ester (300 mg, 0.928 mmol) in ethanol (20 ml) was treated with sodium hydroxide in water (5 ml) followed by 4-chloro-2-fluorobenzonitrile (144 mg, 0.928 mmol) and the mixture stirred at room temperature under nitrogen overnight. The reaction mixture was heated under reflux for 0.5 h, cooled, poured into water and extracted with ethyl acetate which was washed with brine and dried over magnesium sulphate. The solvent was evaporated and the residue eluted down a flash chromatography column using ether/isohexane (3:7) as eluent to give 160 mg of the carbamate protected product as a colourless oil. This material was stirred with 4M hydrogen chloride in dioxan (6 ml) for 1.5 h, evaporated, triturated with ether to give the title compound (122 mg, 37%) as a colourless solid. MS APCI+vem/z317 ([M+H]+). 1H NMR 300 MHz (d6-DMSO) 8.76 (2H, brs), 7.83 (1H, d), 7.71 (1H, d), 7.48 (1H, d of d), 7.43-7.26 (5H, m), 4.96 (1H, t), 2.94 (1H, br m), 2.75 (1H, br m), 2.50 (3H, s), 2.28 (2H, m).

The synthetic route of 4-Chloro-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Millichip, Ian; US2003/73685; (2003); A1;,
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Related Products of 86770-80-1, 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. 86770-80-1 name is 3,3-Difluorocyclobutanecarbonitrile, 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.

Compound 10-3 (7.0g, 59.78mmol), NH3 ? H2O (7mL) and Raney nickel (7.0g, 100%/W) were dissolved in ethanol (70mL) and the mixture was stirred for 3 hours in H2 (50 psi) atmosphere at room temperature. Then the mixture was filtered, added 10mL of 4M hydrochloric acid methanol solution, and concentrated to give Compound 10-4 (5.5g, 58.4%) as a white solid

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

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Hui; DONG, Yanyan; EP2738156; (2014); A1;,
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Synthetic Route of 628-20-6, The chemical industry reduces the impact on the environment during synthesis 628-20-6, name is 4-Chlorobutyronitrile, I believe this compound will play a more active role in future production and life.

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

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-Chlorobutyronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
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3047-38-9, name is Cyclopent-1-enecarbonitrile, 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. name: Cyclopent-1-enecarbonitrile

Into a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-3-amine (1-1; 250 g, 1.04 mol), ethanol (3000 mL), cyclopent-l-ene-l-carbonitrile (300 g, 3.22 mol), and DBU (317 g, 2.08 mol). The resulting solution was heated to reflux and stirred overnight. The reaction mixture was cooled and concentrated in vacuo, and the resulting residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10-1 :2) to afford racemic-2-[3- amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 -yljcyclopentane- 1 -carbonitrile. The racemic 2-[3-amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 – yljcyclopentane- 1 -carbonitrile (100 g, 300 mmol) was purified using Chiral Prep-SFC with the following conditions: Column Used: Phenomenex Lux Cellulose-4, 2 x 25cm, 5 muiotaeta Mobile phase: C02 (80%), methanol with 0.1% DEA (20%) Wavelength: UV 254 nm. Peak A, 1-6: (lR,2R)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane- 1 -carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H). Peak B, 1-7: (llS’,2lS,)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane-l- carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H).

The synthetic route of 3047-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
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Application of 3759-28-2, These common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)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.

100ml of water was added to the reaction vessel, 20mmol (o-cyanophenyl)acetonitrile, 40mmol of potassium (m-tolyl)trifluoroborate 0.4mmol palladium acetylacetonate, 0.8mmol nitrogen ligands L-1, and p-toluenesulfonic acid monohydrate 100mmol, in The reaction was stirred at 60 deg.] C for 30 hours.AntiAfter should be ended, the mixture was poured into ethyl acetate, sequentially with saturated NaHCO3solutionand brine, the aqueous layer was extracted with ethyl acetate, the organic layers combined (i.e., combined washedorganic layer and the extract obtained the organic layer), dried over anhydrous of Na2the SO4dried, vacuum is removed by evaporationof the solvent, the residue was purified by flash column chromatography (hexane / ethyl acetate, volume ratio of between1: 1) to give the target liquid product.The yield was 72.5%,% purity was 99.1(the HPLC).

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

Reference:
Patent; Wenzhou University; CHEN, JIUXI; LIU, MIAOCHANG; CHENG, TIANXING; WANG, XIAODONG; GAO, WENXIA; HUANG, XIAOBO; WU, HUAYUE; (14 pag.)CN104557701; (2016); B;,
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