Month: June 2021

Application of 40497-11-8, A common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

In a 250 mL round bottom three-necked flask, 0.01 mol of 2,6-dimethylaniline and a small amount of ethanol were added,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly dropping into the flask,After the reaction was completed 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction 2 h.Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,A portion of the solvent was evaporated under reduced pressure to crystallize to yield 1.02 g of product,Yield 48.5%

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 103146-25-4,Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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 test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [()-4-] [ [4-DIMETHYLAMINO-L- (4′-FLUOROPHENYL)-L-HYDROXYBUTYL]-3-HYDROXYMETHYLBENZONITRILE,] 10 mg [OF NOVOZYM 435] (product [OF NOVOZYMES),] 0.29 m mol of various kinds of acyl donor and 1 ml of diisopropyl ether, and stirred at [30C] for 16 hours. For the substrate with the optical purity of at least 30% ee, E-values were calculated. The results are shown in Table 8.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 50397-74-5,Some common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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 solution of compound 54-1 (1 g, 5.08 mmol, 1 eq.) in DMF (7 mL) and TEA (2.18 g, 21.55 mmol, 3 mL, 4.25 eq.) was added compound 54-2 (683.15 mg, 6.09 mmol, 783.43 uL, 1.2 eq.),(48.33 mg, 253.77 umol, 0.05 eq.) and Pd(PPh3)2C12 (178.12 mg, 253.77 umol, 0.05 eq.). The mixture was stirred at 90 C under nitrogen atmosphere for 3 hours. TLC showed a new one spot formed. The reaction mixture was diluted with water (20 mL), extracted with EtOAc (20 mLx2),washed with brine (20 mL), dried with sodium sulfate, filtered and concentrated. The residue waspurified by flash silica gel column chromatography (PE:EA = 5:1) to give compound 3 (1 g, yield:86%) as a yellow oil. ?H NMR (400MHz, CDC13) 3 = 7.52 (d, J 1.6 Hz, 1 H), 7.34 (dd, J 8.6, 1.8Hz, 1 H), 6.68 (d, J= 8.4 Hz, 1 H), 4.76 (s, 2 H), 2.95 (s, 1 H), 2.88 (s, 1 H), 2.32 (s, 1 H), 1.85 -1.70 (m,4H), 1.10 (t,J7.4Hz,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-3-bromobenzonitrile, its application will become more common.

Reference:
Patent; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 1211596-75-6, The chemical industry reduces the impact on the environment during synthesis 1211596-75-6, name is Methyl 2-cyano-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

Reference Example 6 Synthesis of 2-cyano-3-(trifluoromethyl)benzoic acid In accordance with the manner of Reference Example 5, the title compound was obtained from 248 mg of methyl 2-cyano-3-(trifluoromethyl)benzoic acid.

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, Methyl 2-cyano-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP2017279; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 26391-06-0, 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. 26391-06-0 name is 2-Cyano-N,N-diethylacetamide, 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.

1: Preparation of racemic 2-cvano-3-(3,4-dihvdroxy-5-nitrophenyl)-N,N-diethylprop-2~ en amide3,4-dihydroxy-5-nitro-benzaldehyde (5Og) and N,N-diethyl-2-cyano acetamide (99.4g) were taken together in dry ethanol (100OmL) and refluxed at 75-8O0C for 15-20min. followed by the addition of ammonium acetate (27g) lot-wise over a period of 24hrs at every 2 hours of interval. After completion of reaction the content was cooled to room temperature and the ethanol was distilled off under vacuum. The residue was taken in dichloromethane (100OmL) and stirred for 15min at 25-300C followed by the addition of purified water (100OmL) and stirred at 25-3O0C for 1 hr. The layer if not cleared was filtered through hyflobed and washed with methylene chloride. The organic layer was separated and the aqueous layer was washed with dichloromethane twice. The organic layer were combined and treated with dilute hydrochloric acid 30OmL (1:1 ratio of HCl and water). The organic layer was separated and treated with purified water to remove any undissolved impurities, the water treatment was repeated two to three times and further the organic layer was treated with activated carbon at 25-30 C and filtered. The filtrate distilled off under vacuum at 600C and the residue was taken in ethyl alcohol at 25-3O0C, stirred for 15- 20min. and distilled off under vacuum at 350C. To the residue was added purified water and the stirred for 2 hrs at 25-300C3 filtered and washed with water and dried to obtain racemic 2-cyano- 3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide.(Dry Weight : 6Og (72.20%), HPLC purity : 98.32%, E isomer (69.80%) and Z isomer (28.52%)

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

Reference:
Patent; NEULAND LABORATORIES LTD; WO2009/84031; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3441-01-8, name is 3-Cyanobenzamide, 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. HPLC of Formula: C8H6N2O

To a vial were added 2-(3-(4-bromophenyl)oxetan-3-yl)-6-chloro-lH- benzo[d]imidazole (50 mg, 0.14 mmol), 3-cyanobenzamide (24.1 mg, 0.165 mmol), (1 S,2S)- N,N’-dimethylcyclohexane-l,2-diamine (7.8 mg, 0.055 mmol), copper(I) iodide (5.2 mg, 0.028 mmol), K2CO3 (44 mg, 0.32 mmol) and dioxane (700 mu). The mixture was evacuated and backfilled with N2 for 4 times, then heated at 120 °C for 17 h. The mixture was filtered and purified by reversed phase HPLC, eluting with water (0.1percentTFA)-ACN to afford the title compound as a TFA salt (Ex. 11). XH NMR (499 MHz, DMSO-c) delta 10.50 (s, 1H), 8.40 (s, 1H), 8.24 (d, J= 7.1 Hz, 1H), 8.07 (d, J = 6.8 Hz, 1H), 7.88 – 7.70 (m, 3H), 7.71 – 7.50 (m, 2H), 7.38 (d, J= 7.5 Hz, 2H), 7.27 (d, J = 7.9 Hz, 1H), 5.36 (d, J= 4.9 Hz, 2H), 5.15 (d, J = 5.0 Hz, 2H); MS (EI) m/z 429 [M+H]+.

The synthetic route of 3441-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 151-18-8, name is 3-Aminopropanenitrile, A new synthetic method of this compound is introduced below., SDS of cas: 151-18-8

10 (150 mg, 0.37 mmol), l^-dicyclohexylcarbodiimide (76.3 mg, 0.37 mmol) and 1- hydroxybenzotriazole (50 mg, 0.37 mmol) were dissolved in DMF (3 ml) and stirred at 05 0C then 3-aminopropionitrile was added drop wise to the above mixture. After stirring for 10 h at 0 0C then for 14 h at ambient temperature, the reaction mixture was poured into ice- cold H2O and extracted with EtOAc. The combined organic extracts were washed successively with IN HCl, H2O, 8% NaHCO3 solution, H2O and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by silica gel o chromatography (EtOAc, 100%) gave 18a (102.2 mg, 60.2%). 1H NMR (400 MHz, CDCl3) delta 8.41 (t, J- 5.72 Hz, IH), 7.27-7.14 (m, IH), 7.07-7.02 (m, IH), 6.96 (s, IH), 6.29 (s, IH), 5.71 (d, J= 8.17 Hz, IH), 3.99-3.95 (m, IH), 3.60-3.46 (m, 3H), 2.65-2.61 (m, 2H), 2.23 (t, J= 7.76 Hz, 2H), 1.36 (t, J= 7.2 Hz, 2H), 1.25-1.14 (m, 8H), 0.86 (t, J= 7.35 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 167.57, 162.27, 157.15, 151.61, 148.85, s 132.82, 126.43, 119.17, 117.90, 117.41, 116.24, 113.69, 113.62, 64.51, 35.89, 33.07, 31.50, 29.80, 29.04, 29.00, 28.74, 22.52, 17.99, 13.98.

The synthetic route of 151-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/54290; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 455-18-5,Some common heterocyclic compound, 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

[4-TRIFLUOROMETHYL-THIOBENZAMIDE] A solution of [A,] a, a-trifluoro-p-tolunitrile (603.5 g, 3.53 mol) in dry DMF (2 L) under N2 [WAS HEATED AT 70XB0;C AND THIOACETAMIDE (505 G, 1.9 EQ. ) ADDED. THE REACTION MIXTURE] was treated with HCI gas for 15 minutes and was stirred at [95XB0;C] for 6 hours. This treatment was repeated 3 times and the mixture stirred at rt for 24 hours. After cooling to [0XB0;C,] water was added and the residue was extracted with diethyl ether (4 L). The organic layer was washed with water (3 L), dried over [NA2SO4] and evaporated. The brownish powder was washed with pentane (3 L) to give the title compound (530.3g, 2.59 mol) as a brown solid in 73% yield ; GC/MS: [M+] [C8H6F3NS] 205

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/6922; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 77326-36-4, A common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, 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 solution of (R)-1-(3-(hydroxymethyl)piperidin-1-yl)-3-methylbutan-1-one5 (Example 34c) (145 mg, 0.73 mmol) in THF (15 mL) was added NaH (44 mg, 1.09 mmol,60% dispersion in mineral oil) at 0 C. The reaction was warmed to room temperature andstirred for 15 minutes, at which time 2-amino-6-fluorobenzonitrile (109 mg, 0.80 mmol) wasadded. The mixture was heated at 80 C overnight, quenched with water, concentrated underreduced pressure to remove THF and extracted with EtOAc (3X). The combined extracts10 were dried over Na2S04, filtered, concentrated under reduced pressure and purified by flashchromatography on silica gel (EtOAc/hexanes). The residue was further purified by chiralHPLC (normal phase, ethanol/isopropanol/methanol/hexanes) to give the title compound as awhite solid (96 mg, 41% ). MS 316 (MH+).

The synthetic route of 77326-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 6136-93-2, 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. 6136-93-2 name is 2,2-Diethoxyacetonitrile, 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.

A solution of 2,2-diethoxyacetonitrile (4.0 g, 30.97 mmol) and sodium methoxide (1.2 mL, 5.4 mol/L, 6.19 mmol) in methyl alcohol (40 mL) was stirred at 25C for 3 hrs, then concentrated to dryness. The residue was taken up in dichloromethane (200 mL) and washed with water (3 x 80 mL) and brine, dried over anhydrous MgS04, filtered and concentrated under vacuum to give methyl 2,2-diethoxyacetimidate (5 g, crude), which was directly used in the next step without purification. LCMS (ESI) [M+H]+ = 162.

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

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; LIANG, Jun; MENDONCA, Rohan V.; SIU, Michael; TELLIS, John C.; WANG, Weiru; WEI, BinQing; CHAN, Bryan K.; CHOO, Edna F.; DROBNICK, Joy Alison; GAZZARD, Lewis J.; HEFFRON, Timothy; (159 pag.)WO2020/72627; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts