Category: 27489-62-9

Reference of 27489-62-9, Adding some certain compound to certain chemical reactions, such as: 27489-62-9, name is trans-4-Aminocyclohexanol,molecular formula is C6H13NO, 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 27489-62-9.

Preparation of Intermediate 21) di-tert-butyl dicarbon .at?e 2) 1,1′-carbonyl trans-4-aminocyclohexanol diimidazole Intermediate 2To a 250ml flask under nitrogen atmosphere was charged DMF (98 mL) and di-t-butyl dicarbonate (63.6g, 0.291 mole). The mixture was stirred at ambient temperature to give a solution. To a second IL flask was charged tfralphakappas-4-aminocyclohexanoI (commercially available) (32.5 g, 0.285 mole) and DMF (160 mL). The mixture was heated to 55-600C to give a solution. Approximately 33% of the di-t-butyl dicarbonate in DMF solution was slowly added to the *r°/s-4-aminocyclohexanol over approximately 30 minutes, keeping the process temperature below 75C during the charge. The mixture was stirred for ~30min- 1 hour at 55-600C. The slow addition of ~33% of the di-t-butyl dicarbonate DMF solution was repeated twice more and the mixture was stirred for ~30min – 1 hour at 55-600C after each addition. After the last addition the reaction mixture was stirred at 70-750C over 1-2 hours. When GC analysis indicated that the ratio between intermediate N-Boc-frflHs-4-aminocyclohexanol and fralpha«s-4-aminocyclohexanol was greater than 33:1, the reaction mixture was cooled to 15-20C. DMF (250 mL) was charged to the reaction and stirred to give a solution. 1, 1′ -Carbonyldiimidazole (59.2g, 1.3 eq) was charged to the reaction in one portion. The reaction was stirred at ~19C for 15 hours and reaction progress was monitored by HPLC. When the HPLC analysis indicated that the ratio between Intermediate 2 and N-Boc~’««,s~4-aminocyclohexanol was greater than 49:1, the reaction mixture was cooled to ~0C. Water (600 mL) was charged slowly to the reaction mixture while keeping the process temperature below ~20C. The white solid product precipitated out of solution. The mixture was cooled to ~ 00C and stirred for 1 hour. The product was filtered and the wet cake was washed with water (100 mL) twice. The product was dried at 60-65C under vacuum to a constant weight. Yield: 82.1 g, 94%.

According to the analysis of related databases, 27489-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 27489-62-9, trans-4-Aminocyclohexanol, 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, Recommanded Product: 27489-62-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 27489-62-9

Step -I: trans-4-(Dibenzylamino)cyclohexanol (intermediate B8-1) [00288] Benzyl bromide (11.36 mL, 96 mmol) was subsequently added dropwise to a stirring solution of trans -4-aminocyclohexanol (5 g, 43.4 mmol) and potassium carbonate (21g, 152 mmol) in acetonitrile (100 mL). The reaction mixture was stirred at 90 C for 16 h, cooled to ambient temperature, filtered through a Celite pad, and washed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was purified using CombiFlash (40.0 g silica gel column; 2% methanol in DCM), to obtain the title product (6 g, 20.31 mmol, 46.8% yield), as an off-white solid. lU NMR (400 MHz, chloroform-d) delta 7.34 – 7.38 (m, 4H), 7.26 – 7.31 (m, 4H), 7.15 – 7.24 (m, 2H), 3.61 (s, 5H), 2.52 (s, 1.96 – 2.06 (m, 2H), 1.88 (br. s., 2H), 1.43 (d, J= 15.31 Hz, 2H), 1.21 (br. s., 2H); MS(ES): m/z 296.2 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27489-62-9, trans-4-Aminocyclohexanol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WASHBURN, William N.; MURUGAIAH SUBBAIAH, Murugaiah Andappan; AHMAD, Saleem; WO2014/39412; (2014); A1;,
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Electric Literature of 27489-62-9, 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 27489-62-9 as follows.

Compound 29 (1.15 g, 10 mmol), CBzCl (2.14 g, 12 mmol) andTEA (1.23 g, 12 mmol) were dissolved in ACN at 0-5 C and stirredfor 1 h. The reaction mixture was diluted with EtOAc and water.The organic layer was separated and washed with water (2 10mL). After drying with anhydrous Na2SO4, the organic layer wastreated with 1 g of silica gel and evaporated under reduced pressureto give a dry plug. This plug was placed on top of a silica gelcolumn and eluted with CHCl3 and MeOH. Fractions containingthe product (TLC) were pooled and evaporated to afford a whitesolid 30 in 90% yield. mp 161.6-163.8 C (lit39 163-165 C); TLCRf 0.49 (CHCl3: MeOH, 20:1); 1H NMR (CDCl3) d 1.25 (m, 2H,CH2), 1.39 (m, 2H, CH2), 1.50 (d, J = 4.00 Hz, 1H, exch, OH), 1.97(m, 4H, CH2), 3.51 (m, 1H, NCH), 3.60 (m, 1H, OCH), 4.60 (br, 1H,exch, NH), 5.10 (s, 2H, CH2), 7.38 (m, 5H, ArH); HPLC >95%; ESIMSm/z [M+H]+, calcd 250.14, found 250.22.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27489-62-9, its application will become more common.

Reference:
Article; Xiang, Weiguo; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2437 – 2451;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 27489-62-9, trans-4-Aminocyclohexanol, 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, Recommanded Product: 27489-62-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 27489-62-9

tert-butyl (trans-4-hydroxycyclohexyl)carbamate To a solution of (1R,4R)-4-aminocyclohexanol (15 g, 0.13 mol) in acetonitrile (240 mL) was added in portions di-tert-butyl dicarbonate (31.2 g, 0.14 mol). The mixture was stirred overnight at room temperature. The precipitate obtained was washed with hexane/ethyl acetate (3:1) and hexane giving the title compound as a white solid (83%). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.17 (br. s., 2 H) 1.44 (br. s., 9 H) 1.32 – 1.40 (m, 2 H) 1.99 (br. s., 4 H) 3.44 (br. s., 1 H) 3.61 (br. s., 1 H) 4.38 (br. s., 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27489-62-9, trans-4-Aminocyclohexanol, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; Prat Quinones, Maria; Fonquerna Pou, Silvia; Puig Duran, Carlos; Lumeras Amador, Wenceslao; Aiguade Bosch, Jose; Caturla Javaloyes, Juan Francisco; EP2386555; (2011); A1;,
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Reference of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

General procedure: A solution of the desired intermediate 3a-l (0.07 mmol, 1 eq) in 1 mL DMSO was taken in a 5mL sealed reaction vessel, the corresponding amine (trans-4-aminocyclohexanol for 4a-k) (0.212 mmol, 3 eq) then diisopropylethylamine (DIPEA)(0.2l2 mmol, 3eq) was introduced. The reaction vessel was then sealed and heated to 140 C for 12 h, cooled and water (25 mL) was added. The aqueous layer was extracted with ethyl acetate (25 mL X 3), the organic fractions were combined and washed with brine (25mL) and dried over sodium sulfate. Purification with column chromatography (S1O2, 4:96 methanokDCM for 4a-k, 5a,5b,5e and 5: 1 :94 methanol :7M NH3 in methanokDCM for 5c,5d,5f,5g) resulted in the desired products which were further purified by preparative TLC to give the desired compounds 4a-k, 5a-g as light yellow solids. 8-(((lr,4r)-4-hydroxycyclohexyl)amino)-3-methyl-6-(3,6,6-trimethyl-4-oxo- 4,5,6,7-tetrahydro-lH-indazol-l-yl)isoquinolin-l(2H)-one (4a): 22 mg, Yield 70%; NMR (400 MHz, Chloroform -if) d 9.16 (d, J= 7.5 Hz, 1H), 9.05 (s, 1H), 6.51 – 6.40 (m, 2H), 6.09 (s, 1H), 3.74 – 3.59 (m, 2H), 3.31 (d, j= 24.2 Hz, 1H), 2.78 (s, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 2.19 (s, 3H), 2.17 – 2.08 (m, 2H), 2.04 – 1.95 (m, 2H), 1.38 (q, 7= 11.1, 9.9 Hz, 4H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCh) d 193.4, 185.3, 169.7, 165.5, 151.4, 150.0, 149.1, 143.5, 143.2, 142.1, 137.4, 107.3, 105.7, 104.8, 100.3, 69.7, 52.4, 50.2, 37.8, 35.8, 33.5, 29.9, 28.4 (2), 19.0, 13.4. HRMS (ESI) m/z [M+H] calculated for C26H33N4O3, 449.2553, found 449.2566.

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; BLAGG, Brian; SANKET, Mishra; (0 pag.)WO2019/232223; (2019); A1;,
Alcohol – Wikipedia,
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Related Products of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

General procedure: A solution of the desired intermediate 3a-l (0.07 mmol, 1 eq) in 1 mL DMSO was taken in a 5mL sealed reaction vessel, the corresponding amine (trans-4-aminocyclohexanol for 4a-k) (0.212 mmol, 3 eq) then diisopropylethylamine (DIPEA)(0.2l2 mmol, 3eq) was introduced. The reaction vessel was then sealed and heated to 140 C for 12 h, cooled and water (25 mL) was added. The aqueous layer was extracted with ethyl acetate (25 mL X 3), the organic fractions were combined and washed with brine (25mL) and dried over sodium sulfate. Purification with column chromatography (S1O2, 4:96 methanokDCM for 4a-k, 5a,5b,5e and 5: 1 :94 methanol :7M NH3 in methanokDCM for 5c,5d,5f,5g) resulted in the desired products which were further purified by preparative TLC to give the desired compounds 4a-k, 5a-g as light yellow solids. 8-(((lr,4r)-4-hydroxycyclohexyl)amino)-3-methyl-6-(3,6,6-trimethyl-4-oxo- 4,5,6,7-tetrahydro-lH-indazol-l-yl)isoquinolin-l(2H)-one (4a): 22 mg, Yield 70%; NMR (400 MHz, Chloroform -if) d 9.16 (d, J= 7.5 Hz, 1H), 9.05 (s, 1H), 6.51 – 6.40 (m, 2H), 6.09 (s, 1H), 3.74 – 3.59 (m, 2H), 3.31 (d, j= 24.2 Hz, 1H), 2.78 (s, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 2.19 (s, 3H), 2.17 – 2.08 (m, 2H), 2.04 – 1.95 (m, 2H), 1.38 (q, 7= 11.1, 9.9 Hz, 4H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCh) d 193.4, 185.3, 169.7, 165.5, 151.4, 150.0, 149.1, 143.5, 143.2, 142.1, 137.4, 107.3, 105.7, 104.8, 100.3, 69.7, 52.4, 50.2, 37.8, 35.8, 33.5, 29.9, 28.4 (2), 19.0, 13.4. HRMS (ESI) m/z [M+H] calculated for C26H33N4O3, 449.2553, found 449.2566.

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; BLAGG, Brian; SANKET, Mishra; (0 pag.)WO2019/232223; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

Imidazole (29.6 g, 434 mmol) was added to (trans)-4-aminocyclohexanol (20 g, 174 mmol), in DCM (200 mL). TBDMS-Cl (39.3 g, 260 mmol) was added portionwise and the reaction mixture was stirred at rt for 18 h. The reaction mixture was evaporated to dryness and redis solved in EtOAc (200 mL) and washed sequentially with water (100 mL), 2 M aq. NaOH (100 mL), water (100 mL) and sat. brine (100 mL). The organic layer was dried over MgS04, filtered and and the solvent was removed in vacuo. The crude product was purified by fee, elution gradient 0 to 10% 1 M methanolic ammonia in DCM, to afford the title compound (30 g, 75%) as a dark golden oil; 1H NMR (500 MHz, CDC13) 0.05 (6H, s), 0.88 (9H, s), 1.05 – 1.22 (2H, m), 1.26 – 1.43 (2H, m), 1.44 – 1.76 (1H, br s) 1.76 – 1.81 (4H, m), 1.82 – 2.29 (1H, br s), 2.67 (1H, tt), 3.51 – 3.63 (1H, m).

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 27489-62-9, trans-4-Aminocyclohexanol, 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, 27489-62-9, blongs to alcohols-buliding-blocks compound. Product Details of 27489-62-9

To a mixture of trans-4-aminocyclohexanol (2.07 g, 13.6 mmol) and NaHCCbeta (3.50 g, 41.7 mmol) in H2O (20 mL) at room temperature, a solution of benzyl chloroformate (1.92 mL, 13.6 mmol) in dioxane (15 mL) was added. The mixture was stirred at room temperature for 20 h. The white precipitate was collected as benzyl (lR,4R)-4- hydroxycyclohexylcarbamate (3.37 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27489-62-9, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
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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. 27489-62-9, name is trans-4-Aminocyclohexanol, the common compound, a new synthetic route is introduced below. Product Details of 27489-62-9

A mixture of Methyl 2-bromo-1 -methyl-1 H-benzimidazoIe-5-carboxylate (37.0 g, 0.137 mol), frans-4-aminocyclohexanol (38.0 g, 0.33 mol), cesium fluoride CsF (29.24 g, 0.29 mol), and DMSO (350 mL) was stirred at 110 C for 6 h and kept overnight at room temperature (TLC control, silica gel, chloroform/ethanol 20:1 ). The reaction mixture was poured into cold water (1.5 L). The precipitate was separated by filtration and recrystallized from acetonitrile (900 mL) to give the title compound in 84% (35.0 g) yield.

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/69053; (2007); A1;,
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Electric Literature of 27489-62-9, 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. 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, The 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 mixture of [6-chloro-4-(tetrahydro-pyran-4-sulfonyl)-pyridin-2-yl]-(5-phenyl-2H- pyrazol-3-yl)-amine formate salt (0.1 g, 0.22 mmol), irans-4-aminocyclohexanol (0.19 g, 1.61 mmol) and DIPEA (0.27 mL, 1.61 mmol) in anhydrous DMSO (1.0 mL) was flushed with nitrogen and heated to 120 C in a sealed tube. Further additions of trans- – aminocyclohexanol (0.19 g, 1.61 mmol) were carried out approximately every 2 – 3h while monitoring by LC-MS until the amount of product did not increase further (no heating or addition of irans-4-aminocyclohexanol overnight). The total heating time was 24h and the total amount of irans-4-aminocyclohexanol added 58.5 equivalents. The reaction mixture was then allowed to cool down to room temperature and partitioned between EtOAc (10 mL) and saturated aq. ammonium chloride solution (5 mL). The phases were separated and the aqueous phase extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried (MgS04), filtered and evaporated in vacuo. The crude material was purified by flash chromatography eluting with MeOH (0 – 10 %) in DCM to give the title compound as a light brown solid (0.07 g, 68 %). XH NMR (500 MHz, DMSO- d6): delta 12.66 (br. s., 1 H), 9.40 (br. s., 1 H), 7.75 – 7.66 (m, 2 H), 7.51 – 7.41(m, 2 H), 7.38 – 7.29 (m, 1 H), 6.93 – 6.74 (m, 2 H), 6.63 (br. s., 1 H), 6.15 (br. s., 1 H), 4.58 (br. s., 1 H), 3.91 (dd, .7=11.2, 3.8 Hz, 2 H), 3.76 (br. s., 1 H), 3.44 (br. s., 2 H), 2.09 – 1.94 (m, 2 H), 1.92 – 1.82 (m, 2H), 1.81 – 1.71 (m, 2 H), 1.66 – 1.48 (m, 2 H), 1.38 – l .l l(m, 4 H). MS: m/z = 498.1 (M+H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 27489-62-9, trans-4-Aminocyclohexanol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
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