Category: 127946-77-4

127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below.

To a solution of Compound 42 (301 mg, 0.854 mmol) in dimethylformamide (4 ml) were successively added 1-aminocyclopropanecarbonitrile hydrochloride (304 mg, 2.56 mmol), triethylamine (0.8 mL, 6.7 mmol) and HATU (812 mg, 2.14 mmol) under nitrogen atmosphere, then the reaction mixture was stirred at room temperature for 2 hours. To the reaction solution was added 10% aqueous sodium bicarbonate solution, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine, then dried over sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound (I-3-1) (220 mg, 62%) as a white solid.Compound (I-3-1); 1H-NMR (DMSO-d6) delta: 1.14 (dd, J=8.36, 5.32 Hz, 2H), 1.49 (dd, J=8.11, 5.58 Hz, 2H), 3.91 (s, 2H), 4.97 (s, 2H), 7.37-7.40 (m, 1H), 7.93 (td, J=7.73, 1.69 Hz, 1H), 8.07 (dd, J=8.62, 2.03 Hz, 2H), 8.27 (dd, J=8.62, 2.03 Hz, 1H), 8.70 (d, J=4.56 Hz, 1H), 8.85 (d, J=1.52 Hz, 1H), 9.23 (s, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shionogi & Co., Ltd.; US2012/253040; (2012); A1;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 127946-77-4

To a 100 mL two-neck flask were added 1-((tert-butylcarbonate)amino)cyclohexanecarboxylic acid (2.43 g, 10 mmol), 1-amino-1-cyclopropanecarbonitrile hydrochloride (1.42 g, 12 mmol) and DMF (15 mL). To the mixture were added HATU (5.32 g, 14 mmol) and ethyldiisopropylamine (8.8 mL, 50 mmol) at 0C under nitrogen protection. The mixture was stirred for 1.0 h at 0 C under nitrogen protection. To the reaction mixture was added saturated aqueous sodium chloride (30 mL), and the resulting mixture was extracted with ethyl acetate (30 mL*3). The combined organic layer was washed with saturated brine (30 mL*3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give light yellow oil (2.82 g, 91%). This crude product was used in next step without further purification.

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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Adding some certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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. 127946-77-4

Into a 25-mL round-bottom flask, were placed (1R,2R)-2-(2-(5-chloropyridin-3-yl)-5-(4- (1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-4,4-difluorocyclohexanecarboxylic acid (10.0 mg, 0.018 mmol, 1.00 equiv), 1-aminocyclopropanecarbonitrile hydrochloride (12.0 mg, 0.101 mmol, 5.74 equiv), HATU (16.0 mg, 0.042 mmol, 2.39 equiv), DIPEA (26.0 mg, 0.20 1 mmol, 11.4 equiv) and DMF (1.5 mL). The resulting mixture was stirred for 16 h at ambienttemperature and diluted with ethyl acetate (5.0 mL). The resulting mixture was washed with brine (5.0 mL). The aqueous layer was extracted with ethyl acetate (3 x 10.0 mL). The combined organic layers were washed with brine (3 x 10.0 mL), dried (Na2504), filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1:1). This resulted in 3.00mg (27%) of(1R,2R)-2-(2-(5-chloropyridin-3 -yl)-5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-N-( 1- cyanocyclopropyl)-4,4-difluorocyclohexanecarboxamide (Compound 2) as a light yellow solid:?H NMR (300 MHz, CDC13) Sppm 9.12 (s, 1H), 8.63 (s, 1H), 8.27 (s, 1H), 7.44 (d, J 9.0 Hz, 2H), 7.02 (d, J= 9.0 Hz, 2H), 5.92 (brs, 1H), 4.08-3.90 (m, 4H), 3.62-3.45 (m, 1H), 3.22-3.11 (m, 4H), 2.91-2.78 (m, 1H), 2.35-2.18 (m, 3H), 2.13-1.91 (m, 3H), 1.48-1.21 (m, 2H), 0.92-0.83(m, 2H); MS (ES, m/z): 632.1 (M + 1), 634.1 (M + 1).

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 1-Amino-1-cyclopropanecarbonitrile hydrochloride.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); 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., 127946-77-4

b) (2S,4S)-4-Hydroxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2 [0151] [0152] To the (2S,4R)-4-methanesulfonyloxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid methyl ester (71.9 g, 200 mmol) were added under stirring and ice-cooling 2.0 M NaOH (120.0 mL, 240.0 mmol) all at once. The ice bath was removed and the white suspension was stirred at room temperature for 1 h. After neutralization by the addition of 2.0 M HCl (20.0 mL, 40.0 mmol; pH 7), 1-aminocyclopropanecarbonitrile hydrochloride (23.7 g 200 mmol) and sodium 2-ethylhexanoate (37.7 g, 220 mmol) were added all at once and the biphasic reaction mixture was stirred at 70 C. for 22 h and then cooled to 35 C. Dichloromethane (100 mL) and NaCl (16 g) were added and stirring was continued until the NaCl was dissolved (15 min). After acidification with 25% HCl (12 mL, pH 1), the reaction mixture was extracted with dichloromethane (3¡Á200 mL) and all three organic layers were washed separately with 5% NaHCO3 (40 mL pH 8). The combined organic layers were dried (Na2SO4), filtered, and evaporated (35-50 C./?5 mbar), affording beige, crystalline residue (88.5 g) which was dissolved in isobutyl acetate (500 mL) at -110 C. Crystallization, which started after seeding and cooling, was completed by stirring at room temperature for 1 h and at -20 C. for 4 h. Filtration and washing with cold isobutyl acetate gave after drying (10 mbar/55 C./4 h) the title product (47.7 g, 72.0%) as an off white, crystalline powder, mp. 156-157 C. [alpha]D20=-68.9 (c 1.0; CHCl3). 1H NMR (CDCl3, 400 MHz) delta 1.15-1.45 (m, 6H), 1.50-1.60 (m, 2H), 2.17-2.29 (m, 2H), 3.72 (dd, J1=11.8 Hz, J2=4.0 Hz, 1H), 3.98 (d, J=11.8 Hz, 1H), 4.40-4.52 (m, 2H), 4.95 (d, J=9.7 Hz, 1H), 7.93 (s, 1H). ESI-MS (m/z) [M+H]+332 (56).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hoffmann-La Roche Inc.; Bartels, Bjoern; Bliss, Fritz; Cueni, Philipp; Pfleger, Christophe; Zutter, Ulrich; US2013/123512; (2013); A1;,
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127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-azanylcyclopropane-1-carbonitrile hydrochloride (671.53 mg, 5.66 mmol), (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-pyridyl)propanoic acid (2 g, 5.15 mmol) and HATU (2.15 g, 5.66 mmol) were suspended in DMF (15 mL). DIPEA (2.63 mL, 15.45 mmol) was added and mixture stirred for 16H at room temperature. The mixture was diluted with EtOAc and washed with water and brine. Organic layer was separated, dried (Na2SO4), filtered and concentrated to get a crude which was purified by column chromatography. Biotage SNAP KP-SiO2 100 g; eluent: solvent A: petroleum ether; solvent B: EtOAc.

The synthetic route of 1-Amino-1-cyclopropanecarbonitrile hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nizi, Emanuela; Sferrazza, Alessio; Fabbrini, Danilo; Nardi, Valentina; Andreini, Matteo; Graziani, Rita; Gennari, Nadia; Bresciani, Alberto; Paonessa, Giacomo; Harper, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1540 – 1544;,
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127946-77-4, A common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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.

Boc-L-phenylalanine (1) (3.77 mmol, 1 Eq), HATU (1.3 Eq) and 1-Amino-1-cyclopropanecarbonitrile hydrochloride (2) (1.3 Eq.) in DMF(5 mL), under argon atmosphere. The resulting solution was stirred at room temperature for 16 h. The reaction mixture was diluted with ethylacetate (10 mL) and washed with a saturated NaHCO3 solution(3¡Á20 mL) and brine (3¡Á20 mL). The organic phase was dried over MgSO4 and evaporated to give a crude residue that was purified by chromatographic column on Flash Silica using ethyl acetate: n-hexane(7:3) as the mobile phase to give a white solid with a good yield.Yield 92%. White solid. Rf=0.9 (Ethyl Acetate: n-Hexane; 7:3). MP.146-147 C. 1H NMR (500 MHz, CDCl3) delta 7.27-7.04 (m, 5H), 4.58 (m,1H), 3.19 (dd, J=13.8, 5.0 Hz, 1H), 2.88 (dd, J=9.5, 5.0 Hz, 1H),1.31 (s, 9H), 1.25 (m, 2H), 1.04 (m, 2H).13C NMR. (125 MHz, CDCl3) delta 142.88, 131.04, 127.69, 126.21,120.81, 107.59, 37.36

The synthetic route of 1-Amino-1-cyclopropanecarbonitrile hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cianni, Lorenzo; Sartori, Geraldo; Rosini, Fabiana; De Vita, Daniela; Pires, Gabriel; Lopes, Bianca Rebelo; Leitao, Andrei; Burtoloso, Antonio C.B.; Montanari, Carlos A.; Bioorganic Chemistry; vol. 79; (2018); p. 285 – 292;,
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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. 127946-77-4 name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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. 127946-77-4

Step 10: N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N1-(1-cyanocyclopropyl)-4-fluoro-L- leucinamide. Diisopropylethylamine (4.2 mL) was added to a 0 C suspension of the acid (1.5 g) from Step 9, 1-amino-1-cyclopropanecarbonitrile hydrochloride (1. 18 g), O-(7-azabenzotriazol-1-yl)-N, N, N’, N’-tetramethyluronium hexafluorophosphate (1.94 g) and DIMETHYLFORMAMIDE (5 mL) and the mixture was reacted at room temperature for 48 hrs. It was then poured on ice and dilute aqueous ammonium chloride. The mixture was extracted with ethyl acetate and ether (1: 1) and the combined organic layers were washed with pH 3 dilute NA2HP04 and brine. The solvents were evaporated to dryness and the residue was purified by chromatography on SI02 using ethyl acetate and hexanes (1: 2) to yield N2-[(1S)- 1- (4-BROMOPHENYL)-2, 2, 2-TRIFLUOROETHYL]-N -(L-CYANOCYCLOPROPYL)-4-FLUORO-L-LEUCINAMIDE in a sufficient purity state for the next step. 1H NMR (CD3 COCD3) No. 8.15 (1H, NH), 7.6 (2H, m), 7.45 (2H, m), 4.35-4. 45 (1H, m), 3.45-3. 55 (1H, M), 1.9-2. 1 (2H, m), 1.75-1. 85 (1H, NH), 1.35-1. 55 (8H, M), 1. 1-1. 15 (1H, M), 0.95-1. 05 (1H, M).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/21487; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts