Tag: M.W=100-200

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. 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 127667-01-0

Synthesis of methyl 2-fluoro-5-hydroxybenzoate 2-Fluoro-5-methoxybenzonitrile (3d, purchased from Alfa Aesar) (5 g, 33 mmol) was dissolved in hydrobromic acid (50 mL) and glacial acetic acid (30 mL), refluxed for 28 hours at 140 C., and then the reaction mixture was diluted with 100 mL ethyl acetate. The reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times. The organic layers were combined and concentrated to give a crude product of 2-fluoro-5-hydroxybenzoic acid (3e), 2.88 g white solid (yield 56%). 1H NMR (600 MHz, DMSO-d6) delta 7.19-7.17 (m, 1H), 7.08-7.04 (m, 1H), 6.95-6.92 (m, 1H); ESI-MS m/z: calculated for 156.02. found 154.91 [M-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; CHENGDU DI’AO PHARMACEUTICAL GROUP CO., LTD.; Ji, Jianxin; Guo, Na; Xue, Ting; Kang, Bingqiang; Ye, Xinfa; Chen, Xin; Zhang, Tao; US2015/51211; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 34916-10-4, name is 4-Oxo-cyclohexanecarbonitrile, 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 34916-10-4, Recommanded Product: 4-Oxo-cyclohexanecarbonitrile

To a solution of 4-cyanocyclohexanone (200 mg, 1 .626 mmol) and CH3NH2 (2M in THE) (0.8 mL, 1.626 mmol) in THF:CH2CI2 (1:1) (4.0 mL) at 0C was added NaBH(OAc)3 (689 mg, 3.252 mmol) and the resulting mixture was stirred at rt for 48 h. Subsquently, the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated to afford 200 mg (89%) of 4-(methylamino)cyclohexanecarbonitrile as a white solid. NMR (400 MHz, DMSO-d6) 2.91 & 2.61 (two signals, 1 H) 2.23-2.24 (m, 3 H) 1.02 – 1.99 (m, 9 H); ELSD/MS (Method 3) (m/z): [M÷H] 139.06.

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

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); A1;,
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Related Products of 21524-39-0, These common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, 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.

EXAMPLE 5 6,2′-Difluoro-5′-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile A mixture of 2,3-difluorobenzonitrile (19.0 g, 137 mmol) and ethanol (200 ml) pre-saturated with ammonia gas was heated at 140 C. in an autoclave for 8 h (terminal pressure 200 psi). The mixture was allowed to cool to ambient temperature and evaporated to dryness. The residue was dissolved in water (400 ml) and extracted with diethyl ether (2*300 ml). The combined organics were washed with water (300 ml) and brine (250 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. Trituration with isohexane (150 ml) afforded 2-amino-3-fluorobenzonitrile (9.8 g, 50%) as an off-white solid: 1H NMR (360 MHz, CDCl3) delta 4.47 (2H, s), 6.65-6.71 (1H, m), 7.14-7.20 (2H, m).

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carling, William Robert; Hallett, David James; Russell, Michael Geoffrey Neil; Street, Leslie Joseph; US2003/55060; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, 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 118431-88-2, Recommanded Product: 3-Cyclopropyl-3-oxopropanenitrile

3-Cyclopropyl-3-oxopropanenitrile (3.30 g, 30 mmol) and4-hydrazinylpyridine-HC1 (3g, 20 mmol) were dissolved in ethanol and the solution was heated at reflux for 12 h. The reaction mixture was concentrated and re-dissolvedethyl acetate. The solution was neutralized with NaOH solution and the aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, then dried over anhydrous Na2SO4. The volatile components were removed on a rotary evaporator and the residues were dissolved in methanol (10 mL) followed by addition of CF3CO2H (10 mL). The reaction mixture was stirred at room temperature for 12 h and the volatile components were removed on a rotary evaporator. The remaining residues were purified by flash column chromatography affording 3-cyclopropyl-1-(pyridin-4-yl)-1H-pyrazol-5-amine in 3.52 g. ?H NMR (300 MHz, MeOD-d4): 8.56 (dd, I = 4.75, 1.58 Hz, 2H), 7.68 (dd, I = 4.74, 1.59 Hz, 2H), 5.58 (s, 1H), 1.84-1.74 (m, 1H), 0.90-0.82 (m, 2H), 0.66-0.60 (m, 2H). ESI-MS calculated for C11H13N4 [M+H]= 201.11; Observed: 201.58.

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHAO, Yujun; ZHOU, Bing; AGUILAR, Angelo; (114 pag.)WO2016/138332; (2016); A1;,
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Application of 33143-29-2, A common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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: The enantioselective epoxidation of 6-CN-2,2-DMB was carried out following the procedure reported elsewhere [13,14]. Briefly,20 mol% of S,S or R,R catalyst with 6-CN-2,2-DMB (0.0625 mmol) as substrate and 0.1875 mmol of KHSO5(Oxonedissolved in 4 mLH2O) as oxygen source were used. The catalyst and 6-CN-2,2-DMB were dissolved in acetone (4 mL), and the reaction was initiated by the stepwise addition of an aqueous KHSO5 solution, where as,the pH value of the reaction mixture was monitored and adjusted to 8.0-8.5 by slow addition of aqueous 5 wt% NaHCO3 solution,under continuous stirring. After complete addition of the aqueous KHSO5 solution, magnetic stirring was stopped and the obtained solid (catalyst and inorganic salts) was recovered by simple filtration, and it was washed with enough water. The obtained dark brown residue (recovered catalyst) was dissolved in 4 mL of acetone and reused in a further reaction. The liquid phase separated from the reaction system was extracted with CH2Cl2, the aqueous phase was discarded, and the organic phase was washed and dried with anhydrous sodium sulfate. The obtained mixture was concentrated under vacuum and the product was analyzed by GC-MS. The effectof 4-phenylpyridine N-oxide (4-PPNO, 0.0125 mmol) as additive, and the reaction temperature were also evaluated.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romanelli, Gustavo; Sathicq, Angel; Vazquez, Patricia; Villa, Aida; Alarcon, Edwin; Grajales, Edwing; Cubillos, Jairo; Journal of Molecular Catalysis A: Chemical; vol. 398; (2015); p. 11 – 16;,
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194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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. Application In Synthesis of 4-Fluoro-2-(trifluoromethyl)benzonitrile

To a solution of frans-1 ,2-diaminocycloheptane dihydrochloride [racemic (±)] (1.0 g, 4.97 mmol) in DMSO (25 ml_) under argon atmosphere was added triethylamine (1 .37 ml_, 9.94 mmol) followed by 4-fluoro-2-(trifluoromethyl)benzonitrile (0.845 g, 4.47 mmol) at RT and the resulting reaction mixture was heated to 45 C. After stirring for 16 h, the reaction mixture was cooled to RT, poured onto ice-water (50 ml_), basified with 1 N NaOH solution, and extracted with ethyl acetate (100 ml_ x 2). The combined organic layer was washed with water (50 ml_) followed by brine (50 ml_), dried over Na2SC>4, and concentrated under reduced pressure to give the title compound (1.1 g) as a brown residue. The crude residue was directly used for next step without further purification.

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

Reference:
Patent; NOVARTIS AG; BOCK, Mark; CHIKKANNA, Dinesh; GERSPACHER, Marc; KHAIRNAR, Vinayak; LAGU, Bharat; PANDIT, Chetan; WO2013/84138; (2013); 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. 591769-05-0, name is 3-Cyclopentylacrylonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Step 2. (3R)- and (3S)-3-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H- pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile. To a solution of 4-(1H-pyrazol- 4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (15.0 g, 0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers), followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN was evaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layer was back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient of ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several times to remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H column, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product. The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors; however, the final product stemming from the second peak to elute from the preparative-HPLC was more active than its enantiomer. The products may be isolated by preparative HPLC or other means known to those of skill in the art for use in Step 3 below. 1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H), 3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03- 1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H),?0.06 (s, 9H); MS(ES): 437 (M+1).

The synthetic route of 591769-05-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (745 pag.)WO2016/24232; (2016); A1;,
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Related Products of 555-21-5, A common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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 1 (10 g, 61.67 mmol) was dissolved in methanol (50 mL).Add 10% Pd/C (1.0g),Replace the reaction system four times with H2,Stir at room temperature overnight in H2 environment (0.5 MPa).TLC analysis, the reaction was complete, and the reaction solution was filtered through celite.The filtrate was concentrated under reduced pressure to give 8.08g of Compound 2,The yield was 99.1%.

The synthetic route of 555-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Zhang Lijie; Sun Yaquan; Gu Huiwen; (12 pag.)CN108409647; (2018); A;,
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These common heterocyclic compound, 54454-12-5, name is 3-Chloro-2-methylbenzonitrile, 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. Recommanded Product: 3-Chloro-2-methylbenzonitrile

Step A Preparation of 2-chloro-6-cyanobenzyl bromide To a refluxing solution of 3-chloro-2-methylbenzonitrile (2.0 g,13.2 mmol) in 20 mL of CCl4 was added 2.6 g (14.4 mmol, 1.1 eq) of N-bromosuccinimide and 0.2 g of AIBN. The solution was refluxed for 3 hours and then cooled, diluted with 500 mL of CH2 Cl2 and washed with 200 mL of H2 O and 200 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was flash chromatographed with 5:1 hexane/ethyl acetate to yield the titled compound (1.4 g, 46%) as a yellow oil. FAB-MS: m/e=230 (M+1) 1 H NMR (400 MHz, CDCl3, ppm) d 7.63 (dd, 1H); 7.58 (dd, 1H); 7.37 (t, 1H); 4.74 (s, 2H).

The synthetic route of 3-Chloro-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5175164; (1992); A;,
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14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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: Methyl (E)-2-Cyano-3-phenylacrylate

General procedure: A solution of 5,5-dimethylcyclohexane-1,2-dione (13, 35.3 mg, 0.10 mmol) and catalyst 7 (5.94 mg. 0.0010 mmol, 10 mol %) in toluene (1.0 mL) was stirred at 0 C for 15 minutes. To this solution was added alkyl (E)-2-cyano-3-phenylacrylate (14, 0.12 mmol) and the mixture was stirred at 0 C until the reaction was completed (TLC monitoring). The solvent was then removed under reduced pressure and the residue was purified by silica gel chromatography to afford the product 15.

The synthetic route of 14533-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ramireddy, Naresh; Abbaraju, Santhi; Zhao, Cong-Gui; Tetrahedron Letters; vol. 52; 50; (2011); p. 6792 – 6795;,
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