Month: December 2020

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 17193-28-1 as follows. Formula: C6H12N2O

To a solution of l-aminocyclopentane-l-carboxamide (0.500 g, 3.90 mmol) in DCM (16 mL) was added TEA (1.359 mL, 9.75 mmol). The mixture was cooled with an ice bath. Butyryl chloride (0.572 mL, 5.46 mmol) in DCM (4 mL) was added dropwise to the stirred solution, and the reaction mixture was at RT for 18 hours. The reaction was diluted with 0 and DCM. The organic phase was collected. The aqueous phase was extracted (2X) with DCM. The combined organic phase was washed with brine, dried over sodium sulfate, and concentrated to give Intermediate 114a (0.300 g, 1.513 mmol, 38.8 % yield) as a solid. LC-MS (Method A2) RT =0.54 min, MS (ESI) m/z: 199.1 (M+H)+. H NMR (400 MHz, CDC13) delta 7.15 – 6.86 (m, 2H), 5.38 – 5.27 (m, 1H), 2.28 – 2.18 (m, 2H), 2.14 – 2.07 (m, 2H), 1.98 – 1.89 (m, 2H), 1.75 – 1.65 (m, 4H), 1.62 – 1.56 (m, 2H), 0.90 – 0.87 (m, 3H).

According to the analysis of related databases, 17193-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 24243-71-8, name is Propane-1-sulfonamide, 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 24243-71-8, Quality Control of Propane-1-sulfonamide

Example 119 1-(2-Chlorobenzyl)-2-Methyl-6-(2-Propanesulfonylcarbamoyl) Benzimidazole By using the method of example 111, 1-(2-chlorobenzyl)-2-methyl-6-(2-propanesulfonylcarbamoyl)benzimidazole (0.417 g) is obtained from 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.400 g) (example 75), N,N’-carbonyldiimidazole (0.431 g), 1-propanesulfonamide (0.328 g) and diazabicycloundecene (0.404 g). 1H-NMR (DMSO-d6, delta): 1.30 (6H, d, J=6.9 Hz), 2.50 (3H, s), 3.81-3.87 (1H, m), 5.62 (2H, s), 6.46 (1H, d, J=7.7 Hz), 7.25 (1H, t, J=7.5Hz), 7.35 (1H, t, J=7.5 Hz), 7.62 (1H, d, J=7.9 Hz), 7.69 (1H, d, J=8.5 Hz), 7.81 (1H, d, J=8.6 Hz), 8.12 (1H, s), 11.8 (1H, s). IR(KBr): 1670 cm-1. mp: 215.0-217.5 C. (R1=2-chlorobenzyl, R7=methyl, R3=-C(O)NR4R5, R4=SO2R6, R5=H, R6=propyl, n=1, y=0)

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; Cell Pathways, Inc.; US6348032; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 317595-54-3, The chemical industry reduces the impact on the environment during synthesis 317595-54-3, name is tert-Butyl (2-aminocyclohexyl)carbamate, I believe this compound will play a more active role in future production and life.

To a solution of N-(tert-butoxycarbonyl)-1,2-cyclohexanediamine (200 mg) and 3-((benzyloxycarbonyl)amino)propionaldehyde (65 mg) in methylene chloride (4 mL), sodium triacetoxyborohydride (133 mg) and acetic acid (18 muL) were added at room temperature, and the mixture was stirred at the same temperature for 5 hours and 30 minutes. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (2-((3-((benzyloxycarbonyl)amino)propyl)amino)cyclohexyl)carbamate (C39, 137 mg). [0841] MS m/z (M+H): 406.3

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 (2-aminocyclohexyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJIFILM CORPORATION; TAKASAKI, Masaru; TSUJINO, Toshiaki; TANABE, Shintarou; OOKUBO, Megumi; SATO, Kimihiko; HIRAI, Atsushi; TERADA, Daisuke; INUKI, Shinsuke; MIZUMOTO, Shinsuke; US2015/45339; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 129686-16-4, name is 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, 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 129686-16-4, Application In Synthesis of 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one

b) (E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide According to the procedure of Preparation 2 (a), except substituting N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (0.90 g, 3.96 mmole) for benzyl acrylate, and substituting 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.60 g, 2.64 mmole) for 2-amino-5-bromopyridine, the title compound (0.85 g, 86%) was prepared as an off-white solid: MS (ES) m/e 375 (M + H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Affinium Pharmaceuticals, Inc.; EP1226138; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 14719-21-2,Some common heterocyclic compound, 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, molecular formula is C5H4F3NO, 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.

To a stirred solution of 6 (1.37 g; 2.45 mmol) in anhydrous DMF (11 mL) were added tetrakis (triphenylphosphine) palladium (0)(286 mg; 0.245 mmol) and CuI (101 mg; 0.532 mmol). The solution was stirred at room temperature for 10 min. Then N-propargyltrifluoroacetamide (1.12 g; 7.43 mmol) and triethylamine (0.68 mL; 4.90 mmol) were added. The reaction was stirred at room temperature for 13 h with exclusion of air and light. Most DMF was removed under vacuum and the residue was dissolved in ethyl acetate (100 mL) . The solution was washed by saturated aqueous NaHCO3 and NaCl respectively, and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using ethyl acetate-hexane (1:3-1.5) and CH3OH- CH2Cl2 (1:30) respectively as the eluent to afford 7 as yellow solid (1.34 g; 94% yield): 1H NMR (400 MHz, CD3OD) delta 7.34 (s, IH, 6-H) , 6.42 (dd, J = 6.2, 7.7 Hz, IH, l’-H), 5.88-5.99 (m, IH, CH2CJf=CH2), 5.28-5.35 (dm, J = 17.3 Hz, IH, one of CH2CH=CJf2), 5.16-5.21 (dm, J = 10.5 Hz, IH, one of CH2CH=CJf2), 4.29 (s, 2H, C?CCJf2) , 4.24 (m, IH, 3′-H), 4.00-4.09 (m, 3H, 4′-H and CJf2CH=CH2), 3.98 (s, 3H, 4-OCJf3), 3.76-3.84 (m, 2H, 5′- H), 2.32-2.45 (m, 2H, 2′-H), 0.94 (s, 9H, C (CH3) 3)/ 0.12 (s, 3H, one of SiCJf3), 0.11 (s, 3H, one of SiCJf3); 13C NMR (100 MHz, CD3OD) 5 165.0, 161.2, 158.1 (q, J = 36 Hz, COCF3), 154.2, 135.6, 125.0, 117.2 (q, J = 284 Hz, COCF3), 117.0, 99.2, 97.3, 86.0, 84.6, 84.5, 80.3, 78.0, 71.0, 64.8, 53.8, 39.0, 30.9, 26.5, 19.3, -5.1, – 5.2; HRMS (FAB+) calculated for C26H37O5N5F3Si (M+H+) : 584.2516, found: 584.2491.

The synthetic route of 14719-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; WO2007/53702; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1788-08-5, These common heterocyclic compound, 1788-08-5, name is 4-Ethynylbenzenesulfonamide, 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.

To a solution of 4-ethynylbenzenesulfonamide (800 mg, 4.419 mmol, Intermediate 71 ) and 4- (azidomethyl)pyridine (583 mg, 4.417 mmol, Intermediate 55) in a mixture of ethanol (10 mL) and water (10 mL), copper sulphate pentahydrate (1 10 mg, 0.442 mmol) and sodium-L-ascorbate (262 mg, 1.323 mmol) were added at 26 C and stirred at 26 C for 16 h. Upon completion, the reaction mixture was concentrated under reduced pressure. The crude was purified by column chromatography (silicagel 100-200 mesh), eluted with 10% methanol in dichloromethane. The pure fractions were collected and concentrated under reduced pressure to afford 4-(1 -(pyridin-4- ylmethyl)-1 H-1 ,2,3-triazol-4-yl)benzenesulfonamide (500 mg, crude) as a brown solid.1H NMR (400 MHz, DMSO-de) delta 8.81 (s, 1 H), 8.65-8.55 (m, 2H), 8.05 (d, J = 8.4 Hz, 2H), 7.89 (d, J = 8.4 Hz, 2H), 7.48 – 7.22 (m, 4H), 5.76 (d, J = 6.7 Hz, 2H). MS m/z [M+H]+= 316.15.

Statistics shows that 4-Ethynylbenzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 1788-08-5.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 121492-06-6, 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 33; 1-{4-[1-(1-Benzyl-piperidin-4-yl)-4-morpholin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-phenyl}-3-(2-methylamino-ethyl)-urea (Scheme 32)49 mg (0.2 mmol) 4-isocyanatophenylboronic acid, pinacol ester was dissolved in 2 mL DME. 0.2 mmol (36 uL) N-Me-N-Boc ethylene diamine was added. The mixture was stirred for 30 min at room temperature. 50 mg 1-(1-Benzyl-piperidin-4-yl)-6-chloro-4-morpholin-4-yl-1H-pyrazolo[3,4-d]pyrimidine was added, followed by 250 uL of a 2M solution of Na2CO3 and 10 mol % Pd(PPh3)4. The mixture was heated under microwave irradiation at 185 C for 6 min. The mixture was cooled to room temperature and 2 mL TFA was added. After stirring at room temperature for 3h the solvents were removed and the mixture was purified by HPLC (TFA buffers) to give 34 mg of the title compound.

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, N-Boc-(2-Aminoethyl)-N-methylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2008/234262; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 153248-46-5, A common heterocyclic compound, 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, molecular formula is C10H19NO3, 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.

To a solution of PPh3 (242 mg, 0.92 mmol) in anhydrous tetrahydrofuran (10 mL) was added DIAD (186 mg, 0.92 mmol) by syringe at 05 C, followed by a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (185 mg, 0.92 mmol) in anhydrous tetrahydrofuran (5 mL). The resulting mixture was poured into a solution of compound 308-3 (100 mg, 0.306 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature and stirred for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 5/1) to afford the title compound 309-13 as a yellow solid (400 mg, crude). LCMS: 510.5 [M+1] .

The synthetic route of 153248-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 630-22-8, 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. 630-22-8 name is 2,2-Dimethylpropanethioamide, 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.

A solution of ethyl 3-bromopyruvate (1.95 g, 10 mmol, 1.0 eq) and 2, 2, 2-trimethyl-thioacetamide (1.17 g, 10 mmol, 1.0 eq) in 20 mL of ethanol was stirred at room temperature for 48 h. The solvent was evaporated under reduced pressure, and the residue was extracted with aqueous sodium bicarbonate and DCM. The DCM layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was separated by column chromatography to give 2-tert-butyl-thiazole-5-carboxylic acid ethyl ester as a colorless oil (1.15 g, 55.0% yield). 1H NMR (400 MHz, CDCl3) delta 8.01 (s, 1H), 4.38 (q, J=7.1 Hz, 2H), 1.46 (s, 9H), 1.37 (t, J=7.1 Hz, 3H). MS m/z (ESI): 214.0 [M+H].

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

Reference:
Patent; Si Chuan University; Yang, Shengyong; Wei, Yuquan; (168 pag.)US2017/305920; (2017); 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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Computed Properties of C8H12N2O2S

General procedure: (10 mmol) of 3,4-dimethoxyphenethylamine (1.1 mmol) and DIPEA (2.2 mmol) was slowly added to a THF solution (10 ml) of triphosgene (0.44 mmol) And stirred for 30-45 minutes. Then, a solution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.1 mmol) in THF (10 ml) was added and stirred overnight. The salt was filtered, and the filtrate was evaporated and column chromatography (EA: Hexane) was carried out to obtain the title compound.

The synthetic route of 35303-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics