Category: 571188-59-5

571188-59-5 , The common heterocyclic compound, 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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.

Toluene (432.0 mL) and 4-(6-amino-pyridine-3-yl)-piperazine-l -carboxylic acid tert-butyl ester (34.3g, 0.123 moles) were charged into 2L 4N RB flask under nitrogen atmosphere at 30¡À5C and stirred for 5-10 min to get brown colored suspension. Reaction mass was cooled to 0¡À5C. Lithium hexamethyldisilazane 1M solution in THF (259.0 mL, 0.258 moles) was added dropwise to the reaction mass through addition funnel by maintaining the reaction mass temperature at 0 ¡À5C. And stirred the reaction mass for 10-15 min at 0 ¡À 5Cto get clear brown colored solution. Add the solution of 2-chloro-7-cyclopentyl-N,N-dimethyl-pyrrolo[2,3-d]pyrimidine- 6-carboxamide (36.0g, 0.123 moles) in 324.0 mL of toluene dropwise to the reaction mass through addition funnel at 0 ¡À5C. Reaction mass temperature was raised to 25- 35C and stirred for lh for reaction completion. (0107) After completion of reaction (by TLC), solvent was distilled off on rotavapor under vacuum at 55-60C to get the brown colored solid. DM water (360.0 mL) and aq. sodium bicarbonate solution (36.0g of sodium bicarbonate was dissolved in 720.0 mL of DM water) were added to the above solid and stirred for 10-15 min. Then methylene chloride (720 mL) was charged to the above solution and stirred for 5-l0min. Layers were separated. Organic layer washed with DM water (720 mL) and layers Separated. Solvent was distilled off from organic layer completely under vacuum at 45-50C on rotavapor to obtain brown colored solid. The solid was leached with methanol (180 mL) at 30 ¡À 5C to afford title compound as pale brown colour solid. Weight of the product: 57.0g (86.6% by theory). Purity by HPLC > 98.0%. (0108) H1 NMR (DMSO-d6): d 9.412 (S, 1 H), 8.167-8.190 (d, 2 H), 8.02-8.03 (d, 1 H), 7.449-7.479 (dd, 1 H), 6.603 (S, 1 H), 4.690-4.778 (m, 1 H), 3.472-3.484 (d, 4 H), 3.062-3.073 (d, 10H), 2.413-2.465 (m, 12 H), 1.92-1.991 (m, 4 H), 1.427-1.65 (m, 10H); Mass m/z (M+l): 535.25

According to the analysis of related databases, 571188-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; ARUNKUMAR, Thiriveedhi; SWAPNA, Kondaveeti; SATHISH, Thumati; NARESH, Ghanta; JANAKI RAMA RAO, Ravi; DURGA PRASAD, Konakanchi; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; (36 pag.)WO2019/142206; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, 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, 571188-59-5, blongs to pyridine-derivatives compound. 571188-59-5

To 2-chloro-4-cyclopentylamino-pyrimidine-5-carboxylic acid ethyl ester (-2 mmol) in butanol (1.7 mL) was added 4- (6-AMINO-PYRIDIN-3-YL)-PIPERAZINE-L- carboxylic acid tert-butyl ester (0.7g). This mixture was heated to 100 C. After 2 hrs, xylenes (2 mL) was added and the temperature was raised to 140 C. Heating was continued overnight. The mixture then was allowed to cool and diluted with ethyl acetate. The organic solution was washed twice with 1 M NAOH (aq), saturated ammonium chloride solution, then brine. After drying over magnesium sulfate, the solvents were evaporated and the residue was purified by chromatography on silica gel eluting with 35-45% ethyl acetate in hexanes to give 4- [6- (5-BROMO-4-CYCLOPENTYLAMINO-PYRIMIDIN-2-YLAMINO)-PYRIDIN-3-YL]- PIPERAZINE-1-CARBOXYLIC acid tert-butyl ester. MS (APCI) M++1 Calc’d, 519.18 ; Found, 520.0.

With the rapid development of chemical substances, we look forward to future research findings about 571188-59-5.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

(10) 2.25 g of the compound of formula (4) was dissolved15ml re-steamed toluene,Under nitrogen protection conditions,Add 13.5 ml (1 mol / L)Lithium hexamethyldisilazide,Reaction 30min,Then, 3 g of the compound of formula (12) (dissolved in 6 ml of reformed toluene)Reaction at low temperature for 4 hours,After the reaction is complete,Add ammonium chloride quenching,Adding methylene chloride extraction,The compound of formula (13) was purified by column chromatography

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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; East China Normal University; Hu Wenhao; Chang Huan; Xu Haiqun; Huang Haifeng; Ma Mingliang; (21 pag.)CN106749259; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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.

In a nitrogen environment at about 25¡À2 C., mix 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbamide and 4-(6-aminopyyrol-3-yl)piperazin-1-carboxyl tert-butylate into tetrahydrofuran THF) added with lithium bis(trimethyl)amine (LiHMDS) and stir for about 1 h to obtain the intermediate 4-[6-[[7-cyclopentyl-6-[(dimethylamino)carbonyl]-7H-pyrrolo[2,3-pyrimidine-2-yl]amino]-3-pyridine]-1-piperazinecarboxyl 1,1-dimethylethylate. Cool the mixture to about 8¡À2 C. and keep the mixture at this temperature while an aqueous hydrogen chloride solution is subsequently added slowly and mixed into the mixture. After that, using a separatory funnel and ethyl acetate as an extracting agent, perform an extraction process in duplicate to acquire the aqueous phase. When the extracted solution is cooled to about 5 C. or lower, slowly add an aqueous sodium hydroxide solution until the pH reaches 12.5. Heat the solution to 25 C. and stir for about 16 h. Next, filter the solution to obtain the solid matter (or filter cake), and rinse the filter cake with DD water until the pH of the rinsing liquid is equal to or lower than 9. Lastly, dry the filter cake at about 55¡À5 C. to yield yellowish brown solids, which are 7-cyclopentyl-N,N-dimethyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, whose molar recovery rate can be 98% or higher, with 98% or higher purity.

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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHUNGHWA CHEMICAL SYNTHESIS & BIOTECH CO. LTD.; Kamani, Satyanarayana; Lu, Tzu-Chiang; Chang, Hsin-Yun; Mai, Chin-Cheng; (30 pag.)US10336763; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, A common compound: 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 2L four-neck round bottom flask,Add 100 g of 2-chloro-4-cyclopentyl-N,N-dimethyl-7H-pyrrole[2,3-d]pyrimidine-6-carboxamide (Formula 2), 104.6 g of 4-(6-aminopyridine- 3-yl) piperazine-1-carboxylic acid tert-butyl ester (formula 1),155.8 g of cesium carbonate, after replacing three times with nitrogen, 800 g of 4-methyl-2-pentanone was added.1.534 g of palladium acetate, 6.38 g of BINAP. After the addition is completed, under a nitrogen atmosphere,The temperature was raised to 90 to 100 C and the reaction was carried out for 3 hours. Cool down to 65 C, add 800g water, 270g n-heptane,10 ml of propylenediamine, cooled to room temperature, filtered, and the filter cake was washed once with 500 g of water.Rinse once with 160g of 4-methyl-2-pentanone/270g of n-heptane mixed solvent.Drying at 60 C gives 4-(6-(7-cyclopentyl-6-(dimethylaminoformyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)aminopyridin-3-yl Piperazine-1-carboxylic acid tert-butyl ester) (Formula 3) 168 g. The yield is 92.2%.Determined by HPLC (area normalization method),4-(6-(7-Cyclopentyl-6-(dimethylaminoformyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)aminopyridin-3-yl)piperidyl The purity of the tert-butyl ester of azine-1-carboxylate was 98.8%.

With the rapid development of chemical substances, we look forward to future research findings about 571188-59-5.

Reference:
Patent; Chongqing San Sheng Industrial Co., Ltd.; Wu Ke; He Wei; Peng Lei; Wang Longlin; Jiang Guangding; Yang Fan; (7 pag.)CN109400612; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

1) Replace the reaction flask three times with inert gas N2,Add 1140g of toluene to the reaction flask.Then, 93 g of 4-(6-aminopyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester was added.Cool down to 20 C,Add 140g of isopropylmagnesium chloride,After the addition is completed within 1 hour,Activated for 30 minutes;Continue to add 95 g of 6-bromo-2-chloro-8-cyclopentyl-5-methyl-pyrido[2,3-D]pyrimidin-7(8H)-one, and complete the addition within 1 hour;Continue to add 140g of isopropylmagnesium chloride,After the addition is completed within 1 hour,The temperature was raised to 60 C for 30 minutes.Until the end of the reaction,By adding dropwise a mixture of acetic acid/tetrahydrofuran (mass ratio of acetic acid to tetrahydrofuran: 1:10), the pH of the solution was adjusted to precipitate a solid, and the temperature was lowered to 0 C, filtered, and the filter cake was dried to obtain a yellow solid powder intermediate I141 g, yield 87%. . The HPLC chromatogram of the obtained Pabsini intermediate I is shown in Fig. 2. As can be seen from Fig. 2, the purity of the intermediate I is99.45%.

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 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; Chongqing San Sheng Industrial Co., Ltd.; Wen Jiandong; Peng Lei; He Wei; Yang Zhikun; Fan Jun; Yang Huan; (11 pag.)CN109336886; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, the common compound, a new synthetic route is introduced below.

In the nitrogen atmosphere, the 6-acetyl-8-cyclopentyl-5-methyl-2-chlorine-pyrido[2,3-d]pyrimidin-7(8H)-one (VI) (1.53 g, 5 mmol), 4-(6-amino-3-pyridinyl)-1- piperazinecarboxylic acid 1,1-dimethylethyl ester (VII) (2.78 g, 10 mmol), Lithium bis(trimethylsilyl)amide (2.0 g, 10 mmol) and methylbenzene of 50 mL were added into the reaction bulb. They were heated up to 50-55 C. and react for 2-3 hours, and then cooled down to the room temperature after the completion of TLC detection reaction. The organic layer was separated out by pouring the reaction mixture into icy water, extraction was conducted for the water layer with methylbenzene for two times, and organic phases were combined. The organic layer was washed with water and saline solution respectively, and dried and concentrated to dry with anhydrous sodium sulfate. The residues obtained were dissolved into the dichloromethane of 50 mL, which was added with the concentrated hydrochloric acid of 5 mL and stirred in the room temperature for 12 hours. The organic phase was separated out and washed with water and solution of 10% sodium bicarbonate. The solvent was recycled under normal pressure and added with diethyl ether to separate solids. The crude products obtained were recrystallized with normal hexane and ethyl acetate, and off-white solid Palbociclib (I) of 1.85 g was obtained; yield: 82.6%; mass spectrometry (EI): m/z 448(M+H).

Statistics shows that 571188-59-5 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; SUZHOU MIRACPHARMA TECHNOLOGY CO., LTD.; XU, Xuenong; (8 pag.)US2017/247380; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. 571188-59-5

A mixture of B1 (30.62 g, 110 mmol) and N, N-dimethylformamide (150 mL) was added to the three-necked flask and the mixture was stirred (1.0 M, 120 mL, 120 mmol) was added to a solution of lithium hexamethyldiamine in tetrahydrofuran (20 mL) at 20 to 30 C After the addition of compound 9 (30.58 g, 100 mmol), the reaction was allowed to proceed to room temperature 20 to 25 C for 6 to 8 hours. Reaction end plus (150 mL), extracted with ethyl acetate (150 mL), and the organic phase was washed with saturated brine (150 mL), dried over anhydrous sodium sulfate. After concentration, the compound 12 was separated by a dichloromethane ethyl acetate mixed solvent column chromatography. 46.21 g, 79%)

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, 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; Hangzhou Kechao Biological Technology Co., Ltd.; Zheng Xuchun; Zhang Yiping; Wu Yihua; (14 pag.)CN106565707; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem