Category: 177906-48-8

177906-48-8, Adding some certain compound to certain chemical reactions, such as: 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, 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 177906-48-8.

1,3-Dibromo-2-propanol (1.70 ml, 16.5 mmol) and sodium carbonate (15.9 g, 150 mmol) were added to an ethanol (300 ml) solution of tert-butyl(trans-4-aminocyclohexyl)carbamate (3.21 g, 15.0 mmol) and the resulting mixture was stirred under heating to reflux overnight. After cooling, insoluble matter was removed by filtration through celite and then the filtrate was concentrated under reduced pressure. The residue was diluted with water, followed by extraction with ethyl acetate. Then the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (15 ml) and imidazole (2.45 g, 36.0 mmol) and tert-butyldiphenylchlorosilane (4.29 ml, 16.5 mmol) were added under ice cooling. After stirring at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate and washed with water and brine in that order. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [chloroform:methanol=10:0-4 10:1 (v/v)] to give 2.45 g (32%) of the title compound as a colorless solid.1H-NMR (400 MHz, CDCl3) delta: 1.01-1.13 (4H, m), 1.06 (9H, s), 1.46 (9H, s), 1.74-1.80 (2H, m), 1.93-2.03 (3H, m), 2.87 (2H, t, J=7.2 Hz), 3.35-3.43 (1H, m), 3.51 (2H, t, J=6.9 Hz), 4.42 (1H, t, J=6.3 Hz), 7.37-7.41 (4H, m), 7.42-7.47 (2H, m), 7.61-7.65 (4H, m).

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 177906-48-8.

Reference:
Patent; Sugimoto, Yuuichi; Uoto, Kouichi; Wakabayashi, Takanori; Miyazaki, Masaki; Setoguchi, Masaki; Taniguchi, Toru; Yoshida, Keisuke; Yamaguchi, Akitake; Yoshida, Shoko; US2012/264738; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, The chemical industry reduces the impact on the environment during synthesis 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, I believe this compound will play a more active role in future production and life.

[0311] To a stirred solution of 5-cyclopropyl-4-iodoisoxazole-3-carboxylic acid (1.0 g, 3.59 mmol) in DMF (10 ml) was added EDCI (0.892 g, 4.66 mmol) and HOBT (0.533 g, 3.94 mmol). The solution was stirred for 10 min at 0 C. Next tert-butyl ((lr,4r)-4- aminocyclohexyl)carbamate (0.769 g, 3.59 mmol) was added and the reaction was stirred at rt for 2hr. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and the solid precipitated was collected by filtration and dried under reduced pressure to obtain a residue. The material was purified by column chromatography to afford tert-butyl ((lr,4r)-4-(5-cyclopropyl-4-iodoisoxazole-3-carboxamido)cyclohexyl)carbamate (0.48 g, 28 %).

The chemical industry reduces the impact on the environment during synthesis trans-N-Boc-1,4-cyclohexanediamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, A new synthetic method of this compound is introduced below., 177906-48-8

To a stirred solution of 1-benzyl-3-methyl-1H-pyrazole-5-carboxylic acid (0.150 g, 0.69 mmol) in DMF (5 mL) was added HATU (0.393 g, 1.0 mmol) and diisopropylethylamine (0.24 mL, 1.4 mmol). The solution was stirred for 10 min at 0oC. tert-Butyl ((1r,4r)-4-aminocyclohexyl)carbamate (0.147 g, 0.69 mmol) was added and the reaction stirred at rt for 2 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain a crude residue which was purified by column chromatography to afford tert-butyl ((1r,4r)-4-(1- benzyl-3-methyl-1H-pyrazole-5-carboxamido)cyclohexyl)carbamate (0.08 g, 25%)

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; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, I believe this compound will play a more active role in future production and life. 177906-48-8

Intermediate 46; N-(5-lodo-imidazo[2,1 -b][1 ,3,4]thiadiazol-2-yl)-N’,N’-dimethyl-irans- cyclohexane-1,4-diamine; Step 1 : (4-Dimethylamino-irans-cyclohexyl)-carbamic acid tert-butyl ester; A solution of N-boc-frans-1 ,4-cyclohexanediamine (1 g, 4.7 mmol, 1 equiv) and formaldehyde (1.39 ml, 18.7 mmol, 4 equiv) was treated with sodium cyanoborohydride (0.926 g, 14 mmol, 3 equiv) and then with acetic acid (1.6 ml, 28 mmol, 6 equiv). The reaction mixture was stirred at room temperature under argon atmosphere overnight. The solvent was removed under reduced pressure, and the crude was suspended in sat. NaHC03 and extracted with dichloromethane. The organic layer was dried over Na2S04, filtered and concentrated to afford the desired product (0.787 g) which was used in the next step of the synthesis without further purification.

The chemical industry reduces the impact on the environment during synthesis 177906-48-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; KURZ, Guido; RICO FERREIRA, Maria del Rosario; SOILAN RODRIGUEZ, David; ORTEGA SORET, Miguel Angel; LINK, Wolfang; RABAL GRACIA, Obdulia; WO2012/20215; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, 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 177906-48-8 as follows.

Example 40 {4-[3-(6-Bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester A mixture of 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine (from Example 38 supra) (1.94 g, 6.27 mmol), trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.61 g, 7.52 mmol), K2CO3 (1.04 g, 7.52 mmol) in DMF (20 mL) was stirred at 140 C. for 15 hours. The solution was then cooled to room temperature and poured into water. The resulted solid was filtered and washed with water. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give {4-[3-(6-bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 0.512 g, 17%). LC-MS: [M+H]+ 487.

According to the analysis of related databases, trans-N-Boc-1,4-cyclohexanediamine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; Soth, Michael; US2012/238564; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics