Category: 151-18-8

Synthetic Route of 151-18-8,Some common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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 DMF (1.6 mL) solution of 3-(2-[[3-(trifluoromethyl)phenyl]amino][1,2,4]triazolo[1,5-a]pyridin-8-yl)benzoic acid (80 mg, 0.201 mmol) obtained in Reference Example 122, 3-aminopropanenitrile (0.016 mL, 0.221 mmol), HATU (91.6 mg, 0.241 mmol), and N,N-diisopropylethylamine (0.042 mL, 0.241 mmol) was stirred for 3 hours at room temperature. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off at reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from hexane and ethyl acetate to give 68.4 mg of the titled compound (yield 76%) in solid form. Melting point: 214-215 C.1H-NMR (DMSO-d6) delta: 2.81 (2H, t, J=6.5 Hz), 3.55 (2H, q, J=6.5 Hz), 7.15-7.26 (2H, m), 7.53 (1H, t, J=8.0 Hz), 7.65 (1H, t, J=8.0 Hz), 7.89-7.97 (3H, m), 8.21 (1H, br s), 8.34-8.41 (1H, m), 8.49 (1H, t, J=1.6 Hz), 8.89 (1H, dd, J=6.7, 1.0 Hz), 8.99 (1H, t, J=5.7 Hz), 10.22 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2010/41891; (2010); A1;,
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Synthetic Route of 151-18-8, A common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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.

Add 284 g of ethyl formate to a 500 mL three-neck bottle.At a certain temperature (see Table 1 for specific temperature selection), slowly add 35g of solid sodium ethoxide at a rate of 1.2g/min and raise the temperature to 10 C.Then add 30 g of beta-aminopropionitrile at a rate of 1.0 g/min.The above reaction solution was poured into a 500 mL autoclave, and stirring was started.Heating to raise the temperature to 65-70 C,The pressure range is 5.0-6.0MPa, and it will naturally drop to 20C after 10h of heat preservation.After suction filtration, the filter cake was washed twice with 25 g of ethyl formate, and the filter cake was dried at 50 C.getAlpha-formyl-beta-formylaminopropionitrileYellowish solid sodium salt 65.8g,The content is 90.4%,The yield was 93.8%.

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

Reference:
Patent; Northeast Pharmaceutical Group Co., Ltd.; Yang Huifen; Zhang Li; Qu Zhuangzhi; (6 pag.)CN108484439; (2018); A;,
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151-18-8, name is 3-Aminopropanenitrile, 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 151-18-8

To a 3-neck round-bottom flask wasadded (S)-3-[5-(3,4-dichloro-phenyl)-1 -(4-methoxy-phenyl)-1 H-pyrazol-3-yl]-2-25 m-tolyl-propionic acid (Example 1; 5.0 g, 9.9 mmol, 1.0 equiv), EDC (4.7 g, 24.7 mmol, 2.5 equiv) and HOST (3.3 g, 24.7 mmol, 2.5 equiv) under nitrogen.A/,A/-Dimethylformamide (50 ml) was added, followed by 3-aminopropanenitrile(1.9 g, 24.7 mmol, 2.5 equiv) and diisopropylethylamine (6.8 ml, 39.6 mmol,4.0 equiv). The reaction mixture was stirred overnight, then was diluted with5 ethyl acetate (200 ml), washed with 1 N HCI (100 ml), H2O (100 mL),10%sodium bicarbonate (100 ml), H2O (100 ml) then brine (100 ml), and dried(sodium sulfate). The solvent was then removed under reduced pressureyielding the desired amide (5.35 g, 99%), which was used in the next stepwithout purification. HPLC: Rt = 7.89 (Method A). MS (ESI): mass calculated10 for C29H26Cl2N4O2, 532.14; m/zfound, 533.3 [M+H]+. 1H NMR (500 MHz,CDCI3): 7.31-7.30 (m, 2H), 7.23 (t, J= 7.4 Hz, 1H), 7.19 (br s, 1H), 7.16-7.14(m, 3H), 7.10 (d, J= 7.4 Hz, 1H), 6.91 (dd, J = 8.5, 2.2 Hz, 1H), 6.87 (d, J= 9.0Hz, 2H), 6.20 (s, 1H), 6.09 (t, J = 6.0 Hz, 1H), 3.90 (dd, J = 9.0, 6.0 Hz, 1H),3.82 (s, 3H), 3.56-3.50 (m, 2H), 3.35-3.31 (m, 1H), 3.08 (dd, J = 14.8, 6.0 Hz,15 1 H), 2.53-2.46 (m, 2H), 2.35 (s, 3H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/5393; (2005); A2;,
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Electric Literature of 151-18-8, 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. 151-18-8, name is 3-Aminopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a schlenk-type flask, corresponding aliphatic amine (2 mmol) and intermediates Y-5 (0. 5 mmol) were dissolved in dry dioxane (5 mL), and then Pd2(dba)3 (0.05 mmol), XantPhos (0.05 mmol) and Cs2CO3 (7.5 mmol) were added. The mixture was refluxed to 105 C while stirring under nitrogen atmosphere. The reaction was followed by TLC until its completion. After cooling, the solvent was evaporated under reduce pressure. The residue was purified by flash column chromatography using ethyl acetate/petroleum ether as eluent to give target compounds Ia-Im and IIa-IIm (except Ii and Iii). For Ii and IIi, the Boc group was further removed using CF3COOH to provide the two compounds.

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

Reference:
Article; Yang, Jiapei; Chen, Wenmin; Kang, Dongwei; Lu, Xueyi; Li, Xiao; Liu, Zhaoqiang; Huang, Boshi; Daelemans, Dirk; Pannecouque, Christophe; De Clercq, Erik; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 294 – 304;,
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Electric Literature of 151-18-8,Some common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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 1-bromo-3-iodobenzene (4.0 g, 14.1 mmol) in DMSO (40 mL) were added 3-aminopropanenitrile (1.5 mL, 20 mmol) , cuprous iodide (2.8 g, 15 mmol) , cesium carbonate (7.0 g, 21.5 mmol) and N, N-dimethylglycine (1.5 g, 14 mmol) in turn. The mixture was stirred at 70 for 5 h and quenched with water (40 mL) . The resulting mixture was extracted with DCM (40 mL × 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted withPE/EtOAc (v/v) 2/1 to give a light yellow oily product (3.0 g, 94) .[0990]MS (ESI, pos. ion) m/z: 225.0, 227.0 [M+1]+

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
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Application of 151-18-8, These common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, 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.

(4S)-4-{[(tert-butoxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid (700 mg, 2.52 mmol) was dissolved in DCM. 3-Aminopropanenitrile (228 mI, 3.03 mmol), DMAP (1.23 g, 10.1 mmol) and EDCI (581 mg, 3.03 mmol) was then added and stirred at rt for 18 h. The reaction mixture was diluted with DCM (50 ml.) and washed with 1 M HCI (50 ml.) and sat NaHCO3 (50 ml_). The organic phase was dried with Na2S04, filtered and concentrated to generate methyl (2S)-2-{[(tert- butoxy)carbonyl]amino}-4-[(2-cyanoethyl)carbamoyl]butanoate (762 mg, 91 %). LCMS [M+H]+ m/z 314; 1H NMR (400 MHz, CDCI3) d ppm 6.86 (br. s., 1H), 5.32 (d, J= 7.3 Hz, 1H), 4.23 – 4.38 (m, 1H), 3.76 (s, 3 H), 3.48 – 3.58 (m, 2 H), 2.65 (t, J= 6.5 Hz, 2 H), 2.29 – 2.36 (m, 2 H), 2.15 – 2.25 (m, 1H), 1.84 – 1.97 (m, 1H), 1.45 (s, 9 H).

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

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; BENGTSSON, Christoffer; BORHADE, Sanjay; HARALDSSON, Martin; HELLEDAY, Thomas; HENRIKSSON, Martin; HOMAN, Evert; PAULIN, Cynthia; SANDBERG, Lars; SCOBIE, Martin; STENMARK, Pal; VALLIN, Karl; (138 pag.)WO2019/201991; (2019); 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. 151-18-8, name is 3-Aminopropanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 151-18-8

To a suspension of (S)-3-(5-benzylisoxazole-3-carboxamido)-5-methyl-4-oxo- 2,3,4,5-tetrahydrobenzo [b][l,4]oxazepine-7-carboxylic acid (87.0 mg, 0.206 mmol) in DCM (2.0 mL) was added l-chloro-N,N,2-trimethylprop-l -en- 1 -amine (33.1 mg, 0.248 mmol) as a solution in DCM (0.10 ml) dropwise over 1 min. The reaction mixture was stirred at rt for lh and became a homogeneous solution. The reaction mixture was cooled in an ice-bath then 3-aminopropanenitrile (57.9 mg, 0.826 mmol) was added dropwise as a solution in DCM (0.25 mL). The ice-bath was removed then 10 % aq citric acid solution was added and the mixture was stirred vigorously for 15 min . The organic phase was separated, washed with sat. aq sodium bicarbonate and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by FCC( EtO Ac-Hex: 60-80%) to yield the desired product(67.0 mg, 68.5 %). MS (m/z) 474.4 (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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); 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. 151-18-8, name is 3-Aminopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A. (S)-N-(2-Cyano-ethyl)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-Phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionamide. To a 3-neck round-bottom flask was added (S)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid (Example 1; 5.0 g, 9.9 mmol, 1.0 equiv), EDC (4.7 g, 24.7 mmol, 2.5 equiv) and HOBT (3.3 g, 24.7 mmol, 2.5 equiv) under nitrogen. N,N-Dimethylformamide (50 mL) was added, followed by 3-aminopropanenitrile (1.9 g, 24.7 mmol, 2.5 equiv) and diisopropylethylamine (6.8 mL, 39.6 mmol, 4.0 equiv). The reaction mixture was stirred overnight, then was diluted with ethyl acetate (200 mL), washed with 1 N HCl (100 mL), H2O (100 mL), 10% sodium bicarbonate (100 mL), H2O (100 mL) then brine (100 mL), and dried (sodium sulfate). The solvent was then removed under reduced pressure yielding the desired amide (5.35 g, 99%), which was used in the next step without purification. HPLC: Rt=7.89 (Method A). MS (ESI): mass calculated for C29H26Cl2N4O2, 532.14; m/z found, 533.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.31-7.30 (m, 2H), 7.23 (t, J=7.4 Hz, 1H), 7.19 (br s, 1H), 7.16-7.14 (m, 3H), 7.10 (d, J=7.4 Hz, 1H), 6.91 (dd, J=8.5, 2.2 Hz, 1H), 6.87 (d, J=9.0 Hz, 2H), 6.20 (s, 1H), 6.09 (t, J=6.0 Hz, 1H), 3.90 (dd, J=9.0, 6.0 Hz, 1H), 3.82 (s, 3H), 3.56-3.50 (m, 2H), 3.35-3.31 (m, 1H), 3.08 (dd, J=14.8, 6.0 Hz, 1H), 2.53-2.46 (m, 2H), 2.35 (s, 3H).

According to the analysis of related databases, 151-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); 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. 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;,
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Related Products of 151-18-8, 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. 151-18-8 name is 3-Aminopropanenitrile, 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.

Example 2 N-(2-cyanoethyl)-3-[1-(2,4-dichlorophenyl)-2,3-dihydro-1H-indol-6-yl]benzamide To a solution of 3-[1-(2,4-dichlorophenyl)-2,3-dihydro-1H-indol-6-yl]benzoic acid (105 mg, 0.27 mmol) obtained in Reference Example 4 and DMTMM (94.3 mg, 0.32 mmol) in DMF (1.5 ml) was added 3-aminopropanenitrile (23.6 muL, 0.32 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (100 mg , yield 85%) as crystals. Melting point 148 – 154C. 1H-NMR (CDCl3) delta : 2.76 (2H, t, J = 6.3 Hz), 3.22 (2H, t, J = 8.3 Hz), 3.73 (2H, q, J = 6.2 Hz), 3.94 (2H, brs), 6.60 (2H, d, J = 1.5 Hz), 6.99 (1H, dd, J = 7.6, 1.6 Hz), 7.21 – 7.29 (2H, m), 7.39 (1H, d, J = 8.5 Hz), 7.45 (1H, t, J = 7.7 Hz), 7.51 (1H, d, J = 2.3 Hz), 7.62 – 7.69 (2H, m), 7.89 (1H, t, J = 1.7 Hz).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2298731; (2011); A1;,
Nitrile – Wikipedia,
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