Tag: M.W=100-200

1558-81-2, A common heterocyclic compound, 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, molecular formula is C7H9NO2, 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.

To a mixture of ethyl 1-cyanocyclopropanecarboxylate (35.9 mmol, 5 g), dimethoxyethane (100 mL) and methanol (10 mL) was added sodium borohydride (287 mmol, 10.87 g) slowly and the mixture stirred at room temperature for 18 hours. The solution was diluted with saturated sodium hydrogen carbonate slowly and then extracted with 10% methanol/dichloromethane (*3). The organic layers were combined, dried over sodium sulphate and concentrated under vacuum to give the intermediate 1-(hydroxymethyl)cyclopropanecarbonitrile (2.36 g). 1H NMR (CDCl3, 400 MHz): delta 0.99 (2H, m), 1.28 (2H, m), 2.5 (1H, br s), 3.62 (2H, s)

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

Reference:
Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); A1;,
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A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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. 1080-74-6.

EXAMPLE 11 Cvclization to Form Dihvdropyridine 16 (R = 2-fury, R3=H) To a solution of 3-dicyanovinylindan-1-one (4.06 g, 20.9 mmol) in 200 mL of ethanol was added 2-furaldehyde (3.01 g, 31.4 mmol) and 25 mL of conc. NH40H. The solution was heated to reflux for 2 h and allowed to cool to rt overnight. The mixture was concentrated in vacuo to remove ethanol. The residue was filtered and washed with water. The purple solid obtained was dried to yield 5.92 g (89%).

The synthetic route of 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL PHARMACEUTICAL, INC.; WO2005/42500; (2005); A1;,
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A common compound: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1080-74-6

The specific operation is as follows: adding the above dialdehyde structural compound 17 (0.20 g) to a 100 mL two-necked bottle,The terminal group 1 (0.21 g), 40 ml of dry chloroform and pyridine (1 ml) were reacted at room temperature for 24 hours.The organic phase was extracted with chloroform, dried over anhydrous sodium sulfate and evaporated.Column chromatography separationBlue-black solid compound 6 (0.25 g, yield 84%).

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, 1080-74-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nankai University; Chen Yongsheng; Qiu Nailiang; Zhang Huijing; Feng Huanran; (32 pag.)CN108864135; (2018); A;,
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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. 939-80-0, name is 4-Chloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 939-80-0

In a flask equipped with a reflux condenser, frans-4-aminocyclohexanol hydrochloride(2.70g, 17.80mmoles) was suspended in iso-propanol (15m1). To this stirred suspension,triethylamine (4,40m1, 31 .49mmoles) was slowly added, followed by 4-chloro-3- nitrobenzonitrile (2.50g, 13.69mmoles). The resulting yellow suspension was heated at 65C for 36h, allowed to cool down to room temperature before water (lOml) was added to the reaction mixture. The resulting precipitate was collected by filtration andsuccessively washed with water and iso-propanol, to yield 4-(((1R,4R)-4- hydroxycyclohexyl)amino)-3-nitrobenzonitrile as a yellow crystalline solid (3 .28g, 12.55mmoles, 92%). The resulting solid was further purified by recrystallization from hot ethanol.mlz 262.2 [MJ-1]+?H NMR (500 MHz, DMSO-d6) oe 8.49 (s, 1H), 8.18 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.1 Hz, 1H), 4.63 (s, 1H), 3.67 (dtd, J = 14.9, 10.4, 4.0 Hz, 1H), 3.57-3.41 (m, 1H), 2.05-1.88 (m, 2H), 1.89-1.75 (m,2H), 1.53-1.19 (m, 4H).

The synthetic route of 939-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; MATHEWS, Neil; WARD, Simon; LUNN, Graham; PARADOWSKI, Michael; GASCON SIMORTE, Jose Miguel; (72 pag.)WO2016/55780; (2016); 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 194853-86-6 as follows. 194853-86-6

General procedure: The mixture of 60% dispersion of NaH (80.0 mg, 2.0 mmol) inmineral oil and 5-bromo-tetrahydroquinoline (3) (212.0 mg,1.0 mmol) in dry DMF (4.0 ml) was stirred at 0 C for 30 min. 4-Fluoro-2-(trifluoromethyl) benzonitrile (378.2 mg, 2.0 mmol) wasadded and the mixture was warmed to room temperature. After2 h, the reaction mixture was quenched with cold water andextracted with ethyl acetate. The organic phase was washed withwater twice and then dried over anhydrous Na2SO4, filtered, andconcentrated under vacuum. Pure 4-(5-bromo-3,4-dihydroquinolin 1(2H)-yl)-2-(trifluoromethyl)benzonitrile (6)was obtained as a yellow solid (100.0 mg, yield 26.2%) after flashcolumn chromatography using a solvent of 10% ethyl acetate inhexanes. For the synthesis of intermediate 5 and 7, commerciallyavailable 2 and 4 were used respectively by the proceduredescribed for intermediate 6.

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
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Adding a certain compound to certain chemical reactions, such as: 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, 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 127667-01-0, 127667-01-0

To a solution of 2-fluoro-5-methoxybenzonitrile (2 g, 13.2 mmoi) in DMSO (6.6 mL) was added l 02 (1.6 mL) and K2C03 (274 mg, 1.98 mmoi). The resulting solution was stirred for 30 mm at it. The reaction was then quenched with NaHC03 (said, 30 mL). The resulting solution was extracted with EtO Ac (50 mL), and the organic layers were combined, and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtO Ac/petroleum ether) on silica gel to obtain compound 36a as a white solid. ^I-NM (400 MHz, DMSQ-t delta (ppm): 7.66 – 7.70 (m, 2H), 7.04 – 7.23 (m, 3H), 3.77 (s, 3H)

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-Fluoro-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (219 pag.)WO2017/27309; (2017); A1;,
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Adding some certain compound to certain chemical reactions, such as: 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, 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 327056-73-5. 327056-73-5

STEP A A mixture of 3-chloro-5-fluoro-benzonitrile (1.1 g, 7.07 mmol), 1-methyl-piperazine (1.18 ml, 10.6 mmol), and K2CO3 (2.92 g, 21.21 mmol) in DMSO (25 ml) was heated to 100C overnight and then partitioned between water and Et2O. The aqueous phase was extracted with Et2O and the collected organic phases were dried over Na2SO4 and evaporated under vacuum. The residue was dissolved in Et2O and extracted with 0.5 M HCl. The aqueous phase was basified with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to give 1.01 g of 3-chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile. Y=61%

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 3-Chloro-5-fluorobenzonitrile.

Reference:
Patent; DAC S.r.l.; EP2033956; (2009); A1;,
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114344-60-4, 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. 114344-60-4 name is 2-Amino-3-bromobenzonitrile, 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.

To a solution of 2-Amino-3-bromobenzonitrile (30.0 g) in THF (240 mL) was added sodium tert-butoxide (1.1 eq.) and the mixture was stirred at -5 to 5C for 1 hour. A solution of intermediate 3a in THF (85.0 g) was then added dropwise and the mixture was stirred for 2-4 hours monitoring the conversion by High Performance Liquid Chromatography (HPLC). Water (210 mL) was then added dropwise and the mixturewas concentrated to remove most of THF. Heptane (300 mL) was then added and the mixture was stirred for 30 mm. After phase separation, the organic layer was washed with water (210 mL), concentrated to 2-3 volumes and filtered through a pad of silica gel (60 g), washing the pad with heptane (300 mL), affording 63.3g of intermediate549.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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71825-51-9, 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. 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

10% Pd/C (300 mg) was added to a solution of 2-methyl-2-(4-nitro-phenyl)- propionitrile (3.00 g; 15.8 mmol), prepared as in l(A), in MeOH (65 mL). The mixture was hydrogenated at 1 bar at room temperature for 2.5 hours, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (2.40 g; 80% yield).LCMS (RT): 0.78 min (Method A); MS (ES+) gave m/z: 161.1 (MH+).

The synthetic route of 71825-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
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1897-52-5, Adding some certain compound to certain chemical reactions, such as: 1897-52-5, name is 2,6-Difluorobenzonitrile, 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 1897-52-5.

Example 94; 5-[1-(2-Trifluoromethylphenyl)-ethoxy]-quinazoline-2,4-diamine; [00287] Step 1; A solution of alpha-methyl-2- (trifluoromethyl)benzyl (750 mg; 3.9 mmol) in dimethylformamide was added to a cooled (0 C) slurry of sodium hydride (156 mg; 3.9 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature, and stirred for 45 minutes. In another vessel, a solution of 2,6-difluorobenzonitrile (543 mg, 3.9 mmol) in dimethylfomamide was chilled to 0 C, and activiated anion was added over 20 minutes. Mixture was then stirred 2 hours at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered, washed with water and dried to afford 1.2 g of solid (99% yield) of 2-fluoro-6-[1-(2-trifluoromethylphenyl)-ethoxy]- benzonitrile.

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 1897-52-5.

Reference:
Patent; DECODE CHEMISTRY, INC.; SINGH, Jasbir; GURNEY, Mark E.; WO2005/123724; (2005); A1;,
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