Category: 151-18-8

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. name: 3-Aminopropanenitrile

To a suspension of (S)-3-((tert-butoxycarbonyl)amino)-5-methyl-4-oxo-2,3,4,5- tetra-hydrobenzo[b][l,4]oxazepine-7-carboxylic acid (185.0 mg, 0.550 mmol) in DCM (5.0 mL) was added l-chloro-N,N,2-trimethylprop-l -en- 1 -amine (88 mg, 0.660 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 (154 mg, 2.200 mmol) was added dropwise as a solution in DCM (0.25 mL). After 10 min, 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, brine then dried over Na2S04and concentrated in vacuo. The residue was purified by FCC [EtO Ac-Hex: 45-80%] to yield the desired product (190.0 mg, 89%).MS (m/z) 389.3 (M+H+).

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

Application 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.

Example 7; N-Cbz-3-aminopropionitriIe (18).; 3-Aminopropionitrile 17 (0.56 g, 8.0 mmol) was suspended in water (10 mL) and THF (10 mL). The pH was adjusted to 9.0 by addition of NaOH (0.2 g, 5 mmol). Benzyl chloroformate (1.7 g, 10 mmol) was added dropwise over 2 h at 20-25 0C to the resulting clear solution, and the pH EPO was kept constant at 9.0 by addition of aqueous NaOH (4 M, 2.5 mL). The mixture was stirred for 1 h at pH 9.0, extracted with ethyl acetate, and dried with Na2SO4. The solvents were removed by rotary evaporation to give crude 18 (1.6 g, 98%) as an oil. 1H NMR (400 MHz, OMSO-d6) delta.3 (s, 5H), 5.0 (s, 2H), 3.22 ~ 3.27 (m, 2H), 2.6 (t, 2H5 J= 6.4 Hz).

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

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 151-18-8 as follows. Recommanded Product: 151-18-8

5 L of an aqueous solution containing 500 g of beta-aminopropionitrile (previously adjusted to pH 8.0 with concentrated hydrochloric acid) was added to a 10-L jacketed mechanically stirred glass reactor.Further, 250 g of a Nitrile hydrolyzing enzyme resting cell prepared by the method described in the patent CN 101701222B was added thereto, and fully suspended by mechanical stirring (250 rpm), and the temperature of the reaction vessel was controlled to 35 C by a constant temperature water bath, and the reaction time was 6 hours.The progress of the reaction was monitored by HPLC during this time.After the substrate was completely transformed, the reaction solution was heated to 90 C, incubated for 30 min, and the cells and denatured proteins were removed by filtration.The filtrate was concentrated and dried to give a mixture of beta-alanine and buffer salt as a solid, which contained 625 g of beta-aminopropionic acid in a yield of 98.4%.

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.

Adding a certain compound to certain chemical reactions, such as: 151-18-8, name is 3-Aminopropanenitrile, 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 151-18-8, HPLC of Formula: C3H6N2

Intermediate 28-2 : N-(2-C yanoethyl)-2-(q r,4s)-5 ‘-(4,4,5,5-tetramethyl- 1 ,3,2- dioxaborolan-2-yl)-2′,3′-dihydrospiro[cvclohexane-l,l’-indenel-4-yl)acetamide3-Aminopropionitrile (0.215 mL, 2.94 mmol) was added to a stirred solution of Intermediate 28-3 (725 mg, 1.96 mmol), N-ethyldiisopropylamine (1.023 mL, 5.87 mmol) and PyBROP (1.369 g, 2.94 mmol) in DCM (50 mL). The resulting solution was stirred at ambient temperature for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (125 mL), and washed sequentially with 2M HCl (75 mL) and saturated brine (75 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (900 mg, 109 %) as a white foam.1H NMR (400 MHz, DMSO) delta 1.09 – 1.20 (2H, m), 1.27 (12H, s), 1.42 – 1.46 (2H, m), 1.53 – 1.67 (4H, m), 1.72 – 1.79 (IH, m), 1.90 (2H, t), 2.03 (2H, d), 2.63 (2H, t), 2.81 (2H, t), 3.26 – 3.29 (2H, m), 7.17 (IH, d), 7.46 (IH, d), 7.48 (IH, s), 8.16 (IH, t); m/z 423 (M+H)+.

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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., name: 3-Aminopropanenitrile

oBromonium iodobenzene(4.0 g, 14.1 mmol) in dimethylsulfoxide (40 mL) was added 3-aminopropionitrile(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), reacted at 70 C for 5 hours, quenched with water (40 mL), extracted with dichloromethane (40 mL x 3), dried over anhydrous sodium sulfate (Eluent: PE / EtOAc (v / v) = 2/1) to give 3.0 g of a pale yellow oil, and the residue was subjected to column chromatography , Yield: 94%.

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; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. name: 3-Aminopropanenitrile

A process for preparing 2-methyl-4-amino-5-aminomethylpyrimidine, comprising the steps of:1), 30 parts of DMF and 50 parts of dimethyl sulfate was added to a four-necked flask, the temperature was raised to 75 C, the reaction was stirred for 4 h, and then cooled to -10 C;2), slowly add 50 parts of sodium methoxide methanol solution, drip, and stir for 10 minutes;3) slowly adding 28 parts of 3-aminopropionitrile, stirring for 40 min, and distilling under reduced pressure to obtain intermediate 1;4), further adding 140 parts of dichloromethane and stirring for 20min, filtering, and the filtrate is subjected to distillation under reduced pressure to obtain intermediate 2;5), 75 parts of sodium methoxide methanol solution was added to a four-necked flask, cooled to -4 C, slowly added 40 parts of acetonitrile hydrochloride, stirred for 30 min, filtered, the filtrate was transferred to another flask and intermediate 2 was added. And 40 parts of sodium hydroxide, liter After warming to 25 C and stirring for 16 h, a solution of 2-methyl-4-amino-5-aminomethylpyrimidine was obtained, and the yield was 92.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 151-18-8, its application will become more common.

Reference:
Patent; Nanjing Jinhao Pharmaceutical Technology Co., Ltd.; Wu Jianzhong; Liu Weiqiang; Tong Hebing; Jiang Lihua; Wang Bucheng; (4 pag.)CN109293580; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 151-18-8, The chemical industry reduces the impact on the environment during synthesis 151-18-8, name is 3-Aminopropanenitrile, I believe this compound will play a more active role in future production and life.

Example 386 N-(3-(((2-cyanoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-6-methylpyridine-2-carboxamide To a solution of 4-(((6-methylpyridin-2-yl)carbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 47 (0.66 g, 2.0 mmol) and 3-aminopropionitrile (0.18 mL, 2.4 mmol) in DMF (15 mL), WSC (0.41 g, 2.4 mmol) and HOBt (0.32 g, 2.4 mmol) were added, and the mixture was stirred at room temperature for 6 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 1:1) to give the title compound (0.75 g, yield 92%) as crystals. melting point 186-187 C. 1H-NMR (CDCl3): delta 1.60-1.80 (3H, m), 2.00-2.15 (2H, m), 2.15-2.30 (1H, m), 2.70 (3H, s), 2.76 (2H, t, J=6.6 Hz), 3.75 (2H, t, J=6.6 Hz), 3.65-3.80 (1H, m), 4.00-4.55 (1H, m), 5.36 (1H, d, J=7.2 Hz), 7.20-7.30 (1H, m), 7.32 (1H, d, J=7.2 Hz), 7.75 (1H, t, J=7.7 Hz), 8.03 (1H, d, J=6.9 Hz), 8.58 (1H, s), 11.53 (1H, s).

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

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route 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.

Example 483 N-(3-(((2-cyanoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-6-methylpyridine-3-carboxamide To a solution of 4-(((6-methylpyridin-3-yl)carbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 56 (0.66 g, 2.0 mmol) and 3-aminopropionitrile (0.18 ml, 2.4 mmol) in DMF (15 ml), WSC (0.41 g, 2.4 mmol) and HOBt (0.32 g, 2.4 mmol) were added, and the mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, passed through a small amount of silica gel and evaporated under reduced pressure. Diethyl ether was added to the precipitated crystals, and the crystals were collected by filtration to give the title compound (0.60 g, yield 86%) as crystals. melting point 118-120 C. 1H-NMR (CDCl3): delta 1.55-1.80 (3H, m), 2.00-2.15 (2H, m), 2.15-2.30 (1H, m), 2.64 (3H, s), 2.74 (2H, t, J=6.6 Hz), 3.65-3.80 (3H, m), 4.00-4.15 (1H, m), 5.36 (1H, dd, J=9.3, 2.1 Hz), 7.26 (1H, d, J=7.5 Hz), 7.20-7.30 (1H, m), 8.07 (1H, dd, J=8.4, 2.7 Hz), 8.50 (1H, s), 9.09 (1H, d, J=2.7 Hz), 10.34 (1H, s).

Statistics shows that 3-Aminopropanenitrile is playing an increasingly important role. we look forward to future research findings about 151-18-8.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); 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., name: 3-Aminopropanenitrile

A solution of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {3-(5-chloro-2-difluoromethoxy-phenyl)-1-[2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl]-1H-pyrazol-4-yl}-amide.dioxane (36 g, 57.0 mmol) in DCM (500 mL) was treated with 3-amino-propionitrile (5.0 mL, 68.4 mmol) and acetic acid (50 mL). The mixture was cooled in an ice bath before the addition of sodium triacetoxyborohydride (18.1 g, 85.4 mmol) portionwise. The reaction was allowed to warm to room temperature and stirred for 1.5 hours. The mixture was diluted with methanol and loaded onto a pad of Isolute SCX-2 which had been conditioned with MeOH. After flushing with MeOH, the product was eluted with 2M ammonia in MeOH. The basic fractions were combined and evaporated to afford pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (3-(5-chloro-2-difluoromethoxy-phenyl)-1-{2-[4-(2-cyano-ethylamino)-piperidin-1-yl]-2-oxo-ethyl}-1H-pyrazol-4-yl)-amide as a pale brown solid (31.1 g, 91%). LCMS (Method 3) [M+H]+=598.2, RT=2.25 min. 1H NMR (400 MHz, CDCl3) delta: (ppm) 9.84 (s, 1H), 8.78 (dd, 1H, J=1.6, 6.9 Hz), 8.69 (s, 1H), 8.58-8.55 (m, 1H), 8.40 (s, 1H), 7.68 (d, 1H, J=2.5 Hz), 7.41 (dd, 1H, J=2.7, 8.7 Hz), 7.28 (d, 1H, J=8.7 Hz), 7.28 (s, 1H), 7.00 (dd, 1H, J=4.2, 6.9 Hz), 6.50 (t, 1H, J=74.1 Hz), 5.08 (d, 1H, J=15.4 Hz), 5.02 (d, 1H, J=15.5 Hz), 4.37 (d, 1H, J=13.4 Hz), 3.88 (d, 1H, J=13.4 Hz), 3.22-3.12 (m, 1H), 3.02 (t, 1H, J=6.4 Hz), 2.98-2.86 (m, 2H), 2.82-2.72 (m, 1H), 2.52-2.46 (m, 2H), 1.96-1.83 (m, 2H), 1.36-1.20 (m, 2H).

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; Genentech, Inc.; Zak, Mark Edward; Ray, Nicholas Charles; Goodacre, Simon Charles; Mendonca, Rohan; Kellar, Terry; Cheng, Yun-Xing; Li, Wei; Yuen, Po-Wai; US2015/336962; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts