Month: September 2021

Some common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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. Formula: C12H18N2O2

Solution of DA-171 (189 mg, 1 mmol) and tert-butyl 3-aminobenzylcarbamate (222 mg, 1 mmol) in MeOH (10 mL) was stirred for 2 days. Solvent was removed in vacuo and residue was purified by MPLC (silica, 0-10% MeOH in DCM) to give white solid of DA-76. DA-76 (382 mg, 0.928 mmol) was dissolved in MeOH saturated with HCI (5 mL). Clear solution was stirred for 2 h and then diluted with diethyl ether. Formed crystals were filtered off, washed with ether and dried in vacuo to give white powder of DA-87. To a solution of DA-87 (50 mg, 0.130 mmol) and 3-phenylpropiolic acid (21 mg, 0.143 mmol) in DMF (3 mL) TEA (66 mg, 0.650 mmol) followed by PPA (50% solution in AcOEt, 99 mg, 0.156 mmol) was added. Deep red solution was stirred overnight, diluted with AcOEt, washed 3x with brine, dried with sodium sulfate and the solvent was removed in vacuo to give pale yellow thick oil. It was purified by MPLC (silica, 0-10% MeOH in DCM) to give colorless glass.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147291-66-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret; WO2013/62945; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 198967-24-7, name is 2-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H10FNO2

Example 48: 4-tert-Butyl-N-[5-chloro-2-(2-fluoro-benzoyi)-pyridin-3-yl]- benzenesulfonamide; [00439] N-(2-Bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl- benzenesulfonamide (140 mg, 300 mmol) was placed in a dry 2-neck 10 mL round-bottom flask. The flask was evacuated and purged with nitrogen, followed by the addition of THF (1 mL). The homogeneous mixture was lowered to -5 C and /PrMgCI (0.33 mL, 2.0 M) was added dropwise. Upon completion of the addition, the reaction was stirred 90 minutes, followed by the slow addition of 2- fluoro-N-methoxy-N-methyl-benzamide (140 mg, 750 mmol). The reaction was stirred overnight, during which the ice-bath warmed to room temperature. The following day, the reaction was quenched with a small quantity of MeOH and the solvents evaporated in vacuo. The residue was subsequently treated with 4.0 M HCI (in dioxane) (1 mL, 4.0 mmol) and H2O (0.33 mL), and then stirred at 80 C for two hours. The resultant solution was diluted with EtOAc, washed with water, saturated sodium bicarbonate, and brine; dried with MgSO4, and evaporated employing reduced pressure. The crude sulfonamide was finally purified via preparatory TLC (20% EtOAc/hexanes) and recrystallization from MeCN/H2O to afford 98 mg of the title compound: 1H NMR (400 MHz, CDCI3) delta 10.6 (s, 1 H), 8.3 (d, 1H), 8.2 (d, 1H), 7.74 (d, 2H), 7.6 (d, 1 H), 7.5 (d, 1 H), 7.43 (d, 2H), 7.42-7.37 (m, 2H), 1.26 (s, 9H); MS (ES) M+H expect 447.1 , found 447.5.

According to the analysis of related databases, 198967-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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. 3144-09-0, name is Methylsulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: Methylsulfonamide

To a stirred suspension of methylsulfonamide (6 g, 62 mmol) in DCM at 0 C. was added DMAP (760 mg, 6.2 mmol), triethylamine (10.4 ml, 74.4 mmol) and (Boc)2O (14.2 g, 65.1 mmol). The reaction mixture was warmed up to room temperature and stirred overnight. The solution was concentrated and the residue was diluted with ethyl acetate, washed consecutively with 1N HCl and water, dried with Na2SO4, filtered and evaporated to afford a colorless oil. The oil was refluxed in hexane for 1 hour then cooled to room temperature and filtered to afford the target compound as a white solid (12.1 g, 42.1% yield). 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.22 (s, 1H), 3.18 (s, 3H), 1.42 (s, 9H).

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; GlaxoSmithKline; US2010/256092; (2010); 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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl methylcarbamate

A solution of aniline (0.911 mL, 10.0 mmol) and di-tert-butyl dicarbonate (2.34 mL, 10.2 mmol) in THF(5.0 mL) was stirred for 1 h at room temperature. The resulting mixture was concentrated to obtain N-tert-butoxycarbonylaniline(10) (2.03 g, quant.) as colorless crystals. The crude product was used without purification. (Step 2) A solution of 10 (545 mg, 2.82 mmol) and (Z)-1-bromo-4-methoxybut-2-ene (11) (422 mg,2.56 mmol) in DMF (8.5 mL) was treated with sodium hydride (60 wt.% in oil, 154 mg, 3.85 mmol) at 0 C. The resulting mixture was stirred for 1 h at 50 C and quenched with saturated aqueous ammonium chloride at 0 C.Extractive workup and purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 5/1 asthe eluent) afforded (Z)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate (12) (654 mg, 92% yield) as acolorless oil. (Step 3) A solution of diisopropylamine (484 L, 3.45 mmol) in THF (4.2 mL) was treated with a1.6 M n-butyllithium hexane solution (2.30 mL, 3.7 mmol) at 0 C under an argon atmosphere and the mixture was stirred for 30 min at the same temperature. A solution of 12 (649 mg, 2.34 mmol) in THF (7.5 mL) was added to the solution at 0 C and the mixture was stirred for 3 h at the same temperature. The resulting mixturewas quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified bychromatography on silica gel (hexane/ethyl acetate = 20/1 as the eluent) to give 2f (516 mg, 90% yield)

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:
Article; Tayama, Eiji; Horikawa, Kouki; Iwamoto, Hajime; Hasegawa, Eietsu; Tetrahedron Letters; vol. 55; 19; (2014); p. 3041 – 3044;,
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. 84713-20-2, name is Benzyl vinylcarbamate, A new synthetic method of this compound is introduced below., Formula: C10H11NO2

General procedure: Unless otherwise noted, the General Experimental Procedure was described as follows: To a solution of enecarbamate/enamide 1 (0.2 mmol) in alcohol (2.0 mL) was added the BNDHP (1.4 mg, 0.002 mmol), and the reaction mixture was stirred at 25 oC. When the starting materials disappeared with the inspection by TLC, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with petroleum ether/EtOAc to afford the product 2. S3

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:
Article; Chang-Fei, Zhang; Wei, Zou; Xiao-Yan, Ma; Xinjun, Hu; Yanli, Li; Tetrahedron; vol. 76; 16; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 676371-64-5, name is Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, belongs to amides-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 676371-64-5, Recommanded Product: 676371-64-5

To a stirring solution of methyl 3-((tert- butoxycarbonyl)amino)bicyclo[1 .1 1 ]pentane-1 -carboxylate (0.2 g, 0.829 mmol) in THF (3.0 ml_), under nitrogen, in an ice bath was slowly added methylmagnesium bromide (3 M in Et20, 5 ml_, 3.32 mmol). After addition, the reaction mixture was stirred in the ice bath for ~10 min and then at rt for ~30 mins. The reaction was quenched with sat. aq. ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude tert- butyl (3-(2-hydroxypropan-2-yl)bicyclo[1 .1 1 ]pentan-1 -yl)carbamate (187 mg, 0.775 mmol, 93 % yield) as a colorless oil. 1H NMR (400 MHz, CD3SOCD3) d ppm 7.39 (br. s., 1 H), 4.1 1 (s, 1 H), 1 .70 (s, 6 H), 1 .37 (s, 9 H), 1 .03 (s, 6 H).

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, Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; CADILLA, Rodolfo; (152 pag.)WO2019/116256; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 317595-54-3, name is tert-Butyl (2-aminocyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C11H22N2O2

The resulting triethylammonium chloride was removed by filtration and to the filtrate was added N-(t-butoxycarbonyl)-trans 1,2-diaminocyclohexane.

The synthetic route of 317595-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Associated Universities, Inc.; US5089663; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 148017-28-1, name is tert-Butyl sulfamoylcarbamate, belongs to amides-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 148017-28-1, category: amides-buliding-blocks

Example 65; N-[((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl]sulfamide (Compound I-56); Step a: tert-butyl(aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate; ((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (700.0 mg, 0.001462 mol), N-Boc-sulfonamide (398 mg, 0.00203 mol) and triphenylphosphine (575 mg, 0.00219 mol) were dissolved in ethyl acetate (28 mL, 0.28 mol) at 50 C. under an atmosphere of nitrogen. Diethyl azodicarboxylate (350.0 muL, 0.002223 mol) was added over 2-3min and the mixture was stirred at 50 C. for 30 minutes. The cooled mixture was evaporated and the residue purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product as a white solid, 636 mg (66%). LC/MS: Rt=2.55 min, ES+ 657 (AA standard).

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; Millennium Pharmaceuticals, Inc.; US2007/191293; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 188345-71-3, 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. 188345-71-3 name is 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, 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.

In a method analogous to J. Malpass and C. Cox, Tetrahedron Lett., 1999, 40, 1419-1422, tert-butyl 2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate is treated with diborane to afford a mixture of alcohols which is separated by chromatography. The desired alcohol tert-butyl 6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate is then oxidized using the Swern procedure to afford the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, and friends who are interested can also refer to it.

Reference:
Patent; Lampe, John W.; Watson, Paul S.; Slade, David J.; US2011/144150; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 67442-07-3, These common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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.

C. Synthesis of Intermediate 22 [0244] A 3-neck flask was charged with 21 (100 g) and THF (800 mL). The solution was degassed three times by slowly applying vacuum, followed by breaking vacuum with nitrogen. The solution was cooled to -10 C. internal temperature. A solution of 2N i-PrMgCl solution in THF (125 g, 1.04 mole equiv) was added slowly while maintaining internal temperature at -10 C. to 0 C. The resulting mixture was then stirred for 30 minutes at -10 C. until reaction was complete. 2-Chloro-N-methoxy-N-methylacetamide (40.6 g, 1.20 mole equiv) was dissolved in MTBE (122 g, 1.22 wt equiv) and filtered through a 1 mum filter. The MTBE solution of the acetamide was then added slowly to the flask maintaining internal temperature at -10 C. to 0 C. Upon completion of the addition, the internal temperature was adjusted to 0 C. and agitated for 2 hours. After the reaction is complete, 1N HCl (750 g) was added slowly so that the internal temperature did not exceed 20 C. If necessary, the internal temperature was adjusted to 20 C. The layers were separated and the aqueous layer was extracted with MTBE (410 g). The organic layers were combined and dried over MgSO4. The MgSO4 was filtered off and rinsed with THF (200 g). The filtrate and rinse were concentrated under vacuum 10 volumes (1000 mL). Isopropanol (785 g) was added and small amounts of crystals began to form. This slurry was again concentrated under vacuum to 10 volumes (1000 mL). Isopropanol (785 g) was once again added and the slurry was concentrated under vacuum to 10 volumes (1000 mL). The internal temperature was adjusted to 20-25 C. and agitated for ca. 30 minutes. The slurry was filtered and rinsed with isopropanol (100 g) then dried under vacuum to provide 62.28 g (70.8%, 98% purity by HPLC) of the product 22 as an off-white to pale yellow solid. 1H NMR (400 MHz, CDCl3, delta): 8.19 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.82 (s, 1H), 7.67 (d, J=8.0 Hz, 2H), 7.52 (d, J=7.8 Hz, 1H), 4.71 (s, 2H). 19F NMR (376 MHz, CDCl3) delta -111.4 (s, 2F).

Statistics shows that 2-Chloro-N-methoxy-N-methylacetamide is playing an increasingly important role. we look forward to future research findings about 67442-07-3.

Reference:
Patent; Scott, Robert William; Wang, Fang; Shi, Bing; Mogalian, Erik; US2013/324496; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics