Category: nitriles-buliding-blocks

1194-65-6, name is 2,6-Dichlorobenzonitrile, 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. Product Details of 1194-65-6

To a solution of Bis(l,5-cyclooctadiene)dimethoxydiiridium (35 mg) in hexane (10 ml) under argon was added 4,4′-Di-tert-butyl-2,2′-bipyridine (1 lOmg). To this dark brown suspension was added pinacol diborane (2.23 g) and the solution was stirred at room temperature for 5 min. To this solution was added 2,6-Dichloro-benzonitrile (1 g) and the mixture was heated at 50C for 22 hours. The solution was then filtered on a Celite pad and the filtrate was concentrated. The residue was then dissolved with ethyl acetate and extracted with saturated ammonium chloride. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was used as such in the next reaction.

The synthetic route of 1194-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; RENOLD, Peter; EL QACEMI, Myriem; PITTERNA, Thomas; TOUEG, Julie Clementine; WO2011/67272; (2011); A1;,
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Synthetic Route of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-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.

Example 10; 3-(4-(5-(8-Bromo-6-(trifluor omethyl)imidazo [ 1 ,2-a] pyridin-2-yl)- 1 ,2,4-oxadiazol-3-yl)-3- methylphenyl) butanoic acid[00364] tert-Butyl 3-(4-cyano-3-methylphenyl) but-2-enoate (52).; To a stirred solution of 4-bromo-2-methylbenzonitrile (5.O g, 26 mmol) in dimethylacetamide (50 mL) was added tert-butyi crotonate (4.35 g, 30.6 mmol) and the reaction mixture was degassed with argon. To this solution, Pd(OAc)2 (0.114 g, 0.510 mmol) was added followed by tetraethylammonium chloride (4.22 g, 25.5 mmol) and the reaction was stirred at 1000C for 15 h. After completion, the reaction mixture was quenched with ice cold water and extracted with ether. The combined organic layers were washed with water, saturated NaCl solution, dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography to afford the title intermediate 52 as a yellow solid (5.2 g, yield 80%).

Statistics shows that 4-Bromo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 67832-11-5.

Reference:
Patent; EXELIXIS, INC.; CANNE BANNEN, Lynne; CHAN, Diva Sze-ming; GU, Xiao-hui; MAC, Morrison, B.; NG, Stephanie; WANG, Tie-lin; WANG, Yong; XU, Wei; WO2010/65760; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, Recommanded Product: 127946-77-4

Example 2; Synthesis of N-(1-cyanocyclopropyl)-2(S)-(1-benzenesulfonyliminoethylamino)-3 -(1-methyl-cyclohexyl)propionamide; (table 2, cpd 19); Step 1; To a stirred solution of 2S-fc^butoxycarbonylamino-3-(l-methylcyclohexyl)propionicacid (283 rng, 1.0 mmol) (prepared as described in Reference H except utilizing 1-methylcyclohexanol intead of 1-methylcyclopentanol) and 1-aminocyclopropanecarbonitrileHC1 salt (178 mg, 1.5 mmol) in DMF (5 mL) at room temperature was added HATU (418 mg,1.1 mmol), followed by diisopropyl ethylamine (0.87 mL, 5 mmol). After being stirred at roomtemperature overnight, the reaction mixture was concentrated under reduced pressure and thenpartitioned between ethyl acetate and brine. The combined organic extracts were dried (MgSCX),concentrated under reduced pressure, and the residue was purified by flash chromatography onsilica gel (eluted with 1: 2 EtOAc/ hexanes) to yield [l-(l-cyanocyclopropylcarbamoyl)-25′-(l-methylcyclohexyl)ethyl]-carbamic acid tert-butyl ester (315 mg, 90%).

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, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AXYS PHARMACEUTICALS; WO2004/108661; (2004); A1;,
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Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, molecular formula is C8H5F3N2, 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. Quality Control of 2-Amino-5-cyanobenzotrifluoride

i. 4-Dibenzylamino-3-trifluoromethyl-benzonitrile, 2 To a solution of 2-amino-5-cyanobenzotrifluoride (1.0 g, 5.37 mmol, 1 eq) and benzyl bromide (2.55 mL, 21.5 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (970 mg, 21.5 mmol, 4 eq) portion-wise under Ar (g). The reaction mixture was stirred at rt overnight, and was then partitioned with H2O (30 mL) and extracted with EtOAc (5*20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to yield the product, 2, as a pale yellow solid (1.66 g, 85%). 1H NMR (400 MHz, CDCl3) deltaH: 7.95 (d, J=2.0 Hz, 1H), 7.63 (dd, J=8.5, 1.5 Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5 Hz, 4H), 7.12 (d, J=8.5 Hz, 1H), 4.23 (s, 4H). MS (ES+) 389.1 (100%, [M+Na]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-74-2, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; Shuttleworth, Stephen Joseph; Silva, Franck Alexandre; US2013/109688; (2013); A1;,
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Electric Literature of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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.

2-[(Benzen-1-yl)methyleneamino]-3-aminomaleonitrile(L) was prepared by a modification of the method described in the literature [18]. To a solution of benzaldehyde (0.500 g,4.71 mmol) in methanol (10 ml), a solution of 2,3-diaminomaleonitrile(0.509 g, 4.71 mmol) in methanol(10 ml) was added dropwise with constant stirring. Theresulting mixture was refluxed at about 80 C for 5 h until completion of the reaction (checked by TLC). The product2-[(benzen-1-yl)methyleneamino]-3-aminomaleonitrile obtained was filtered off and purified by column chromatography(ether:dichloromethane) to afford a yellowish-brown solid.Yield: 0.847 g (84percent); Elemental analyses (C, H and N,wtpercent) Anal. Calc. for C11H8N4: C, 67.3; H, 4.1, N, 28.5;found: C, 67.3; H, 4.09; N, 28.5percent; IR (KBr, m/cm-1): 3404 s,3298w, 2237w, 2204 s, 1605 s; 1HNMR(CDCl3; 300 MHz):d 8.46 (s, 1H, HC=N), d 7.46?7.96 (m, 5H, phenyl), d 7.45 (s,2H,NH2); 13CNMR(CDCl3; 300 MHz): d 156.61(HC=N), d128.99?128.88 (phenyl-C), d 115.84 (CN), d 114.85 (CN), d113.61 (HCNC=C), d 104.65 (CNC=C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diaminomaleonitrile, its application will become more common.

Reference:
Article; Devkule; Chavan; Transition Metal Chemistry; vol. 42; 4; (2017); p. 347 – 356;,
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Adding a certain compound to certain chemical reactions, such as: 17626-40-3, name is 3,4-Diaminobenzonitrile, 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 17626-40-3, Safety of 3,4-Diaminobenzonitrile

EXAMPLE 1A: 2-[l-(3-PHENYL-PYRAZrN-2-YL)-PIPERIDrN-4-YL]-lH- BENZOIMIDAZOLE-5-CARBOSTEP 1. TERT-BUTYL 4-(5-CYANO-lH-BENZO[D]IMIDAZOL-2-YL)PIPERIDTNE-l- CARBOXYLATE; [00186] To the solution of piperidine- 1 , 4-dicarboxylic acid mono-tert-butyl ester ( 15 g, 65.5 mmol) in DMF (50 niL) and pyridine (50 niL) was added CDI (10.6 g, 65.5 mmol) at 45 C and the mixture was stirred for another 2h at this temperature. Then 3, 4-diamino-benzonitrile (8.7 g, 65.5 mmol) was added and the mixture was stirred at RT overnight. Solvents were removed in vacuo and the residue was dissolved in HOAc (20 mL) and heated for lh at 100 C. Then the reaction mixture was concentrated and the residue was partitioned between DCM and aqueous of a2C03. The organic layer was dried over Na2S04 and concentrated to give the crude product which was purified by column chromatography (ethyl acetate: petroleum ether=l :2) to give the compound tert-butyl 4-(5-cyano-lH-benzo[d]imidazol-2-yl)piperidine-l-carboxylate (8 g, 65%) as pale solid.

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, 3,4-Diaminobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; ANDREWS, Kristin L.; FROHN, Michael J.; HARRINGTON, Paul E.; PICKRELL, Alexander J.; RZASA, Robert M.; WO2011/143129; (2011); A1;,
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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. 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Fluoro-4-nitrobenzonitrile

XIX.1 3-(2-Fluoro-1 -fluoromethyl-ethoxy)-4-nitro-benzonithle1 ,3-Difluoro-propan-2-ol (4.2 g) was dissolved under argon in THF (250 ml) and cooled to 0C. LiHMDS (28 ml) was added to the mixture and stirred at rt for 1 hour. Then the mixture was cooled to 0C and 3-fluoro-4-nitrobenzonitrile (1 .95 ml) was added in portions and stirred for 2 hours. The mixture was poured in water and extracted with DCM. The organic layer was washed with water, dried andconcentrated.Yield: 4.9 g

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 218632-01-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; KLEY, Joerg; LEHMANN-LINTZ, Thorsten; REDEMANN, Norbert; SAUER, Achim; THOMAS, Leo; WIEDENMAYER, Dieter; BLACK, Phillip; BLACKABY, Wesley; LINNEY, Ian; AUSTEN, Matthias; DANILEWICZ, John; SCHNEIDER, Martin; SCHREITER, Kay; WO2011/104340; (2011); A1;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Amino-1-cyclopropanecarbonitrile hydrochloride

The carboxylate (1 g, 1.82 mmol) and 1-amino-1-cyclopropanecarbonitrNe hydrochloride (0.2 16 g, 1.82 mmol) was suspended in DMAC (5 ml) and the stirred suspension was cooled down to 3C and then HATU (0.83 g, 2.2 mmol) was slowly added. The reaction mixture was then stirred for 15 mm and then dilsopropylethytamine (DIEA, I ml, 5.5 mrriol) was added. The mixture was stirred at 5C for another 4 hours (check by TLC 50/1 chloroform/methanol), then at -5C for 3 hours. The reaction was terminated by slow dropwiso addition of water (6 ml) at 5C and the suspension was stirred for 1 hour more. The precipitate was isolated by filtration and washed with a mixture of DMAC-H20 (10 ml – 10 ml) and dried in vacuo (180 mbar) at 45C. A white crystalline product of 0.66 g was obtained (84%, HPLC 91. 00%).

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 127946-77-4.

Reference:
Patent; ZENTIVA, K.S.; BABIAK, Peter; ZEZULA, Josef; (12 pag.)WO2016/95879; (2016); A1;,
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Electric Literature of 67237-76-7, 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. 67237-76-7, name is Ethyl 2-(2-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 250 ml four-necked flask with stirring, thermometer and distillation system,23.3 g (0.1 mol) of N-phenyl-2-chloro-2-(pyridin-2-yl)ethylamine (II2) (commercially available) was added.20.5 g (0.11 mol) of ethyl 2-cyanophenylacetate, reacted at 105-110 C for 4 hours.At the same time, the removed ethanol is distilled off, and the gas phase detection reaction is completed. Cool down to 50-60 C,Add 50 g of methyl tert-butyl ether, cool to room temperature, and filter.The filter cake was washed with 20 g of methyl tert-butyl ether and dried.33.8 g of N-phenyl-N-[2-chloro-2-(pyridin-2-yl)]ethyl-2-cyanophenylacetamide (IV2) were obtained.The yield was 89.8%, and the gas phase purity was 99.6%.

The synthetic route of Ethyl 2-(2-cyanophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Ju Lizhu; Zhang Mingfeng; (10 pag.)CN110028442; (2019); A;,
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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 120315-65-3 as follows. Recommanded Product: 120315-65-3

Preparation 42 tert-butyl 2-(4-cyano-2 methoxyphenyl)acetate [0219] Combined (2-(tert-butoxy)-2-oxoethyl)zinc(II) chloride (4.24 mL, 2.122 mmol) and 4-bromo-3-methoxybenzonitrile (0.30g, 1.42 mmol) in THF (4.29 mL), then 2′- (dicyclohexylphosphino)-N,N-dimethyl-[l, l’-biphenyl]-2-amine (0.056 g, 0.141 mmol) and Pd(dba)2 (0.041 g, 0.071 mmol) were added and the reaction was refluxed at 100C overnight. The reaction mixture was concentrated down by rotary evaporation and purified on a silica gel column eluting with hexanes and EtOAc to give the title compound as a yellow oil (102 mg, 29%). MS m/z [M+H]+ 248.

According to the analysis of related databases, 120315-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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