Tag: M.W=200-300

Reference of 1835-65-0, A common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, 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.

Synthesis of Exemplified Compounds (P-1-1), (P-2-1), and (P-3-1)Under nitrogen atmosphere, in 50 ml of 1-methyl-2-pyrrolidone, were dissolved 3.0 g (15 mmol) of tetrafluorophthalonitrile, 1.5 g (5.0 mmol) of synthesis intermediate (B), and 0.99 g (10 mmol) of copper chloride (I), and then stirred for 3 hours at 180¡ã C. After cooling the reaction mixture to room temperature, it was poured into 200 ml of a 5percent hydrochloric acid. Consequently, blue crystals were precipitated. These crystals were separated by a filtration under reduced pressure, followed by washing with water and then acetonitrile, and thereafter drying. Further, they were boiled with 50 ml of acetonitrile for 1 hour, and allowed to cool down to room temperature. The resultant precipitates were separated by a filtration under reduced pressure, and then dried. Thereby was obtained 2.2 g (Yield: 45percent) of a mixture (PP-1) (Melting point>200¡ã C.) containing the exemplified compounds (P-1-1), (P-2-1), and (P-3-1) of the present invention; and hexadecafluoro cupper phthalocyanine (F16CuPc).A mixing rate of phthalocyanine derivatives was measured by a liquid chromatography mass spectrometric analysis (LCMS). The result in terms of area ratio was as follows: (P-1-1):(P-2-1):(P-3-1):(F16CuPc)=54.0:26.4:4.1:15.5 (Since a molar absorption intensity of each of (P-1-1), (P-2-1), (P-3-1), and (F16CuPc) at a detecting wavelength of 254 nm is almost same, the ratio measured from the area results in equal to a molar ratio.).Measuring conditions: TSK gel ODS-80Ts (2 mm Phi.x.150 mm), elute: a mixed solution of A/B (volume ratio 3:7) from 0 minute to 15 minutes, and a mixed solution of A/B (volume ratio 15:85) from 15 minutes to 20 minutes) (elute A: water, elute B: a mixed solution of tetrahydrofuran/methanol (volume ratio 9:1)), flow rate: 0.2 ml/min, a detecting wavelength 254 nm, structural determination by atmospheric pressure chemical ionization (APCI)-mass spectrometry (MS) (It was confirmed using MS that a peak at the retention time=8.185 minutes was (F16CuPc), a peak at the retention time=11.676 minutes was (P-1-1), a peak at the retention time=13.905 minutes was (P-2-1), and a peak at the retention time=14.350 minutes was (P-3-1)). A peak was detected in the blank at the retention time of from 0 to 4 minutes, so that a measurement was started from 4 minutes.

The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; US7947826; (2011); B2;,
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Related Products of 30041-95-3, These common heterocyclic compound, 30041-95-3, name is Ethyl 2-(4-cyanophenoxy)acetate, 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.

General procedure: Intermediates 14 were prepared by following the knownprocedure [22, 29, 30]. The mixture of ethyl 2-chloroacetate(1 mmol), substituted phenols (1 mmol), and K2CO3(1.2 mmol) in acetonitrile was stirred in refluxing for 2 h(the course of the reactions was monitored by TLC), thenfiltered, and the mother liquid was evaporated in vacuo toafford corresponding substituted ethyl 2-phenoxyacetates,which were then reacted with hydrazine hydrate (80%) toyield substituted 2-phenoxyacetohydrazides 14 in>90%yield.

The synthetic route of 30041-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yanyan; Lu, Xiumian; Shi, Jun; Xu, Jiahong; Wang, Fenghua; Yang, Xiao; Yu, Gang; Liu, Zhiqian; Li, Chuanhui; Dai, Ali; Zhao, Yonghui; Wu, Jian; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 611 – 623;,
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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. 72054-56-9, name is 4-(2-Bromoethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(2-Bromoethyl)benzonitrile

Production Example 12 Synthesis of 4-carbamoylphenethyl bromide 4-Cyanophenethyl bromide (0.997 g) was dissolved in sulfuric acid (20 ml) and stirred at room temperature for 15 hr. Then it was poured into ice, diethyl ether was added thereto and the layers were separated. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.619 g) as colorless crystals (yield: 62.0%) 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.23(2H, t, J=7.3Hz), 3.59(2H, t, J=7.3Hz), 7.31(2H, d, J=8.4Hz), 7.78(2H, d, J=8.4Hz).

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 72054-56-9.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)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. COA of Formula: C8H3ClF3N

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

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

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, 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: Ethyl 2-cyano-4,4-diethoxybutyrate

A solution of 55 in 50% TFA/DCM (10 niL) was stirred at room temperature for 17 h. The solution was concentrated to afford the title compound, which was used in the next step without purification.57 2-(4-(Morpholinomethyl)phenylamino)-7H-pyrrolo[2,3-rf]pyrimidin-4-ol (57)[0292] To a microwave reaction tube was charged with 56 (10.0 mmol), 2-cyano-4,4- diethoxy-butyric acid ethyl ester (2.3 g, 10.0 mmol) and NaOMe (25% by wt in MeOH; 15 mL) in EtOH (5 mL). The reaction tube was sealed and the solution irradiated with microwave at 160 0C for 30 min. After cooling to room temperature, the mixture was concentrated. The residue was taken up in water (10 mL) and the pH adjusted to 1 with 6M of HCl. The resulting solution was stirred at room temperature for 25 min and then the pH adjusted to 9 with concentrated 10% NaOH. The resulting solid was filtered, washed with water and dried under high vacuum to afford the title compound as a brown solid. The material was used in the next step without purification.

The synthetic route of 52133-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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Reference of 1255870-63-3, A common heterocyclic compound, 1255870-63-3, name is 4-Bromo-2-ethoxybenzonitrile, molecular formula is C9H8BrNO, 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.

A suspension of 4-bromo-2-ethoxybenzonitrile (1.50 g, 6.5 mmol), hydroxylamine hydrochloride (913 mg, 13 mmol) and NaHCOs (1.365 g, 16.3 mmol) in water (1.32 mL) and EtOH (26.6 mL) is stirred in a sealed tube at 90C for 6h. Once at RT, the product precipitated from the RM upon addition of water. The solid is filtered off under high vacuum, washing with water and some EfeO. A first crop of pure title compound (947 mg) was thus obtained as white solid. The filtrate is extracted with EtOAc. The organic layer is then washed twice with brine, dried over MgS04, filtered and concentrated. The residue is purified by FC (hept/EtOAc 1 :1) to yield another crop of the pure title compound as a white solid (448 mg), merged with the first batch from precipitation. The title compound is obtained as a white solid (1.395 g, 83%). LC-MS B: tR = 0.53min, [M+H]+ = 259.12.

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; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (223 pag.)WO2018/210994; (2018); A1;,
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Related Products of 79463-77-7, A common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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.

Intermediate 122 (100 mg, 0.27 mmol) was dissolved in isopropanol (5 mL) and DIPEA (52.7 mg, 0.41 mmol) and diphenyl N-cyanocarbonimidate [79463-77-7] (79.7 mg, 0.32 mmol) were added. The reaction mixture was stirred at r.t. for ~1 h. p-Toluidine [106-49-0] (31.9 mg, 0.30 mmol) was added and the reaction mixture was stirred at r.t for ~4 h. The reaction mixture was heated at 80 C for 30 minutes. The precipitate was filtered, washing with isopropanol and Et20 to afford the title compound (70 mg, 0.15 mmol, 54%). LCMS [M+H]+478.2, [M+Na]+ 500.2, RT 2.174 minutes, 100.0% purity (Method 1).

The synthetic route of 79463-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
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Reference of 501420-63-9,Some common heterocyclic compound, 501420-63-9, name is 2-(3-Bromo-4-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

(3-Bromo-4-fluorophenyl)acetonitrile (4.00 g, 18.32 mmol), bis(pinacolato)diboron (5.22 g, 20.15 mmol), potassium acetate (55.86 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.2% of Pd) (393.53 mg, 0.55 mmol) were dissolved in oxygen-free 1,4-dioxane (40 ml, max. 0.005% of water) under argon. The reaction mixture was subsequently heated at a temperature of 130 C. for 90 min. When the reaction conversion was complete, the mixture was filtered through kieselguhr. The filtrate was diluted with dichloromethane (200 ml) and water (50 ml) and extracted. The organic phase was dried over sodium sulfate, subsequently filtered and evaporated to dryness in vacuo, giving [4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile as oil (7.59 g, purity 81%, MS: 262.2 [M+H+]), which was reacted further without further work-up.

The synthetic route of 501420-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; FUCHSS, Thomas; EMDE, Ulrich; BUCHSTALLER, Hans-Peter; MEDERSKI, Werner; (224 pag.)US2016/83401; (2016); A1;,
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Synthetic Route of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

3-(4-Bromo-3,5-dimethyl-phenyl)-1H-tetrazole 4-Bromo-3,5-dimethyl benzonitrile (3.0 g, 14.3 mmol), sodium azide (2.32 g, 35.7 mmol) and ammonium chloride (2.3 g, 42.84 mmol) are suspended in dry N,N-dimethylformamide and heated at 140 C. for 7 hours. The mixture is allowed to cool to room temperature, diluted with water and the precipitated solid collected by filtration, washed with water and dried to give the title compound (yield 1.74 g). The mother liquor was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic extracts were combined and the solvent removed to give a second crop of title compound (yield 1.39 g, total yield 3.13 g). LC (MIL-07-002): tR=0.83 min; Mass spectrum (ES+): m/z=253/255 [M+H]+.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
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Electric Literature of 17823-40-4, These common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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.

A mixture of 4-cyanophenylboronic acid (1.83 g, 8 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1.0 g, 3.9 mmol), Pd2(dba)3 (0.18 g, 0.2 mmol), SPhos(0.16 g, 0.4 mmol) and K3PO4 (2.0 g, 8.7 mmol) in toluene (40 mL) was degassed and heated at about 120 C for about 16 hours. After cooled to room temperature, the mixture was filtered and washed with toluene. The filtrate was loaded on silica gel and purified by flash column using eluents of dichloromethane/hexane (10%to 40%). The desired fraction was collected and concentrated to give a white solid (Compound 10) (0.367 g, in 34% yield).

Statistics shows that 4-Bromo-2,3,5,6-tetrafluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17823-40-4.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
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