Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, 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 389890-43-1, Recommanded Product: tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

General procedure: To a solution of (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3- methyl-1H-pyrazolo[3,4-d]pyrimidine (435b) (150 mg, 0.39 mmol), triphenylphosphine (206 mg, 0.79 mmol), tert-butyl cis-4-hydroxycyclohexylcarbamate (127 mg, 0.59 mmol) in THF (3 mL) at 0 C was added dropwise DIAD (0.12 mL, 0.59 mmol). The reaction mixture was stirred at RT overnight, concentrated in vacuum and the residue obtained was purified by flash column chromatography [silica (12 g), eluting with EtOAc in hexane from 0-60%] to furnish tert-butyl ((tra5)-4-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-l-yl)- 6-chloro-3-methyl-lH-pyrazolo[3,4-d]pyrimidin-l-yl)cyclohexyl)carbamate (435c) (150 mg, 66 % yield) as a white solid;1H MR (300 MHz, DMSO-d) delta 6.83 (d, J = 7.9 Hz, 1H), 4.54 – 4.38 (m, 2H), 3.90 – 3.63 (m, 4H), 3.32 – 3.22 (m, 1H), 2.55 (s, 3H), 2.13 – 1.75 (m, 10H), 1.39 (s, 1 1H), 0.82 (s, 9H), -0.05 (s, 6H); MS (ES+): 579.3 (M+l).

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, tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 49805-30-3,Some common heterocyclic compound, 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one, molecular formula is C6H7NO, 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.

(a) (1S,4R)-tert-Butyl 3-oxo-2-Azabicyclo[2.2.1]hept-5-ene-2-carboxylate (+)-2-Azabicyclo[2.2.1]hept-5-en-3-one (Chiroscience, Cambridge, England; 54.565 g, 0.500 mole) was dissolved in dry tetrahydrofuran (350 mL). Di-tert-butyl carbonate (Aldrich, 114.87 g, 0.510 mole as 97%) and 4-dimethylaminopyridine (Aldrich, 600 mg) were added to the stirred mixture. The resulting solution was stirred at ambient temperature for 2 hours. Solvent was evaporated under reduced pressure and the residual orange solid was crystallized from toluene-hexanes to give title compound as white crystals (95.72 g, 91%), m.p. 85-86 C.; 1H-NMR (CDCl3) delta: 1.50 (s, 9H), 2.24 (app AB q, J=8.4 Hz, 2H), 3.39 (br s, 1H), 4.96 (m, 1H), 6.66 (m, 1H), 6.89 (m, 1H). Anal. Calcd. For C11H15NO3: C, 63.14; H, 7.21; N, 6.69. Found: C, 63.20; H, 7.26; N, 6.65.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Azabicyclo[2.2.1]hept-5-en-3-one, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6630477; (2003); B1;,
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. 711007-44-2, name is 2,3-Diaminobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2,3-Diaminobenzamide

General procedure: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
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. 1565-17-9, name is 4-Acetylbenzenesulfonamide, A new synthetic method of this compound is introduced below., SDS of cas: 1565-17-9

General procedure: A mixture of the appropriate arylsulfonyl chloride (11.2 mmol), the corresponding arylsulfonamide (12.3 mmol), DMAP (0.274 g, 2.24 mmol), and Et3N (1.95 mL, 14.0 mmol) in toluene (0.5 M) was kept at 70 C for 12 h (monitored by TLC). The reaction was quenched with aq 2 M HCl (30 mL) to pH 1. The mixture was extracted with EtOAc (3 × 20 mL) and the combined organic layers were dried (anhydrous MgSO4). The solvent was evaporated, and the crude product mixture was purified by recrystallization using hot CHCl3/hexane to afford the desired product.

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; Jeong, Yuri; Ban, Jaeyoung; Lim, Minkyung; Rhee, Hakjune; Synthesis; vol. 50; 9; (2018); p. 1867 – 1874;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 122334-37-6, 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 122334-37-6 as follows.

In a dry round bottom flask is added in excess of the cutting and 1000 ml tetrahydrofuran, then dropwise 1 – bromo ethyl cyclopropane (1 muM), the resulting mixture at room temperature under stirring for 3 hours, the reaction is filtered, to remove the magnesium chips, formula (II) compound of tetrahydrofuran solution (1 mol/L). The reaction is as followsThe embodiment 1 to obtain the compounds of formula (I) compound structure (0.10 muM), tetrahydrofuran (250 ml) are added to a reaction in the bottle, in the -20 C dropping embodiment 2 of formula (II) to obtain a compound of tetrahydrofuran solution 100 ml, then completing, at this temperature to continue the reaction […] 3 hr, the reaction after the reaction is dropped to 250 ml with cold water, then completing, filtering to remove the solid, the collection of organic phase, drying and reducing pressure concentration and crystallization, shall be 1 – (4 – chlorophenyl) -2 – cyclopropyl -1 – acetone product 18.4 g, in formula (I) compounds of structure the idea receives rate is 88.2%, HPLC purity through detection of 99.3%.

According to the analysis of related databases, 122334-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Weifang Runfeng Chemical Co., Ltd.; Sun Guoqing; Hou Yongsheng; Song Jian; (7 pag.)CN108610246; (2018); A;,
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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H18N2O2

To a solution of 4,5-dibromo-2,3-dihydropyridazin-3-one (461.0 mg, 1.82 mmol, 1.2 equiv.) in DMA(10 mL, 107.55 mmol) were added tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6- carboxylate(300 mg, 1.51 mmol, 1 equiv.) and DIEA(391.1 mg, 3.03 mmol, 2 equiv.) at ambient temperature. The resulted mixture was stirred for 16 h at 100 degrees C. The reaction mixture was diluted with water(200 mL) and extracted with ethyl acetate(3*200 mL).The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions(Column: spherical C18, 20-40 um,330g; Mobile Phase A: Water(5mmol/L NH4HCO3), Mobile Phase B: MeCN; Flow rate: 80 mL/min; Gradient: 10% B to 60% B in 55 min; 254 nm) to afford tert-butyl 3-(5-bromo-6-oxo-1,6- dihydropyridazin-4-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate(230mg,40.95%) as a light yellow solid.

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; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121492-06-6, 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. 121492-06-6 name is N-Boc-(2-Aminoethyl)-N-methylamine, 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.

To a solution of N-methyl-N-Boc-ethylenediamine (2.05 ml, 11.48 mmol) and NaCNBH3(685 mg, 10.9 mmol) in MeOH (20 mL) was added 2,4,6-trimethoxybenzaldehyde (2.14 g,10.9 mmol) as a solution in MeOH/DCM 1:1 v/v (40 ml) over 2 h. The mixture was stirred at room temperature for 1 h, acidified with 0.4 M HC1 (60 mL) and stirred further 30 mm. The reaction mixture was extracted 4 times with 150 mL ethyl acetate. The combined organic phase was washed with sat. NaHCO3 solution (200 mL) and brine (90 mL), dried overNa2SO4 and the solvents were evaporated under reduced pressure. The resulting N-methyl-NBoc-N?-Tmob-ethylenediamine 2a was dried in vacuo and used in the next reaction step without further purification.Yield: 4.02 g, 99%, colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Boc-(2-Aminoethyl)-N-methylamine, and friends who are interested can also refer to it.

Reference:
Patent; ASCENDIS PHARMA A/S; BISEK, Nicola; WEISBROD, Samuel; BIGOTT, Kornelia; (116 pag.)WO2018/11266; (2018); 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. 1882-71-9, name is 2-Amino-5-methoxybenzamide, A new synthetic method of this compound is introduced below., Product Details of 1882-71-9

General procedure: A solution of anthranilamide (30 mmol) in 1 N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirring at 0 C, 30% NaOH solution was added slowly to adjust the pH to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered off with suction, washed with deionized water (200 mL), and dried to afford compound 4 in yield of 82%.

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; Chen, Xiulei; Jia, Haowu; Li, Zhong; Xu, Xiaoyong; Chinese Chemical Letters; vol. 30; 6; (2019); p. 1207 – 1213;,
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. 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, A new synthetic method of this compound is introduced below., Product Details of 116861-31-5

A mixture of 3.8 g (12.88 mmol) ethyl 7-bromo-3-hydroxynaphthalen-2-carboxylate, 3.0 g (15.5 mmol) 1-(tert.-butoxycarbonylamino)-3-chloropropane (prepared according to Helv. Chim. Acta 76 (1993), 1644), 2.0 g (14.5 mmol) potassium carbonate, and a catalytic amount of potassium iodide in 20 ml dry DMF was stirred at 90 C. for 6 h. It was poured into water, extracted three times with ethyl acetate, and the combined organic layers were washed three times with water, dried over sodium sulfate, and concentrated in vacuo. The intermediate was purified by chromatography on silica gel with toluene/acetone 9:1 to give 5.8 g (100%) of a yellow oil, which solidified rapidly upon standing.

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; Takeuchi, Kumiko; Jirousek, Michael Robert; Paal, Michael; Ruhter, Gerd; Schotten, Theo; US2004/9976; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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. category: amides-buliding-blocks

General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2-3 equiv) and absolute ethanol (2-3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 C for 12-72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5%ether in pentane. The following compounds were prepared:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39549-79-6, its application will become more common.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics