Month: January 2021

Application of 67442-07-3, 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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

iPrMgCl*LiCl (Turbo Grignard, 1.3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromo-pyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30¡ã C. The mixture is stirred in the cooling bath for 1 h. 2-Chloro-N-methoxy-N-methylacetamide (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCl solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1?1:1) to give the title compound. Mass spectrum (ESI+): m/z=234/236/238 (Br+Cl) [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-N-methoxy-N-methylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; WAGNER, Holger; PETERS, Stefan; (43 pag.)US2018/148411; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 56619-93-3, The chemical industry reduces the impact on the environment during synthesis 56619-93-3, name is N-(3-Methoxyphenyl)pivalamide, I believe this compound will play a more active role in future production and life.

Synthesis of N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (1b) Under the argon atmosphere, n-butyllithium (nBuLi) (2.6 M in THF, 111 mL, 289 mmol, commercial product) was slowly dropped at 0C into a tetrahydrofuran (THF) (400 mL, dehydrated, commercial product) solution of the compound 1a (30.0 g, 145 mmol). After the mixture was stirred at 0C for 2 hours, ethylene oxide (1.3 M ether solution, 175 mL, 228 mmol, commercial product) was slowly added to the mixture and stirred at 0C for 1 hour. The temperature was raised to room temperature, and then the mixture was further stirred for 2 hours. The mixture was concentrated under reduced pressure, to which a saturated ammonium chloride aqueous solution (sat. NH4Cl aq.) was added. Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (100 mL * 4). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized with ethyl acetate (EtOAc), and thus N-[2-(2-hydroxyethyl)-3-methoxyphenyl]pivalamide (compound 1b) (28.1 g, 112 mmol, 77.1%) was obtained as a colorless solid. TLC Rf= 0.40 (n-hexane/EtOAc = 3/1)

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-(3-Methoxyphenyl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyoto University; National University Corporation Tokyo Medical and Dental University; Kinopharma, Inc.; HAGIWARA, Masatoshi; ONOGI, Hiroshi; KII, Isao; HOSOYA, Takamitsu; SUMIDA, Yuto; EP2881397; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1012884-46-6, name is 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one, molecular formula is C17H12ClNO2, 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. COA of Formula: C17H12ClNO2

Example 1; Preparation of trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (IV); following Scheme II A. Mixture of trans-(IV) and cis-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (V); Under N2 atmosphere, iodine (4.95 g, 18 mmol) was added to a stirred suspension of magnesium (1.75 gram, 71.87 mmol) in toluene (175 mL). Over a period of 20 minutes, a solution of 11-chloro-2,3-dihydro-2-methyl-1H-dibenz[2,3;6,7]oxepino[4,5-c]pyrrol-1-one (III) (25 gram, 84 mmol; see Vader et al., above) in methanol (175 mL) was added. The reaction mixture was stirred for 35 minutes. Then, over a period of 2 hours, 3 portions of magnesium (1 g, 41.06 mmol) followed by one larger portion of magnesium (2 g, 82.12 mmol) were added. Water (600 mL) and 36% hydrochloric acid (65 mL) were added keeping the temperature below 40 C. Toluene (50 mL) was added, the layers were separated, and the water layer was extracted with toluene (2¡Á100 mL). The combined toluene layers were washed with water (200 mL), dried over magnesium sulfate, filtered and evaporated. This gave a mixture of trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino [4,5-c]-pyrrol-1-one (IV) and cis-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (V) (25.5 g, 100%) in the ratio (IV):(V)=1:4 as determined by 1H-NMR and GC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1012884-46-6, its application will become more common.

Reference:
Patent; Organon Ireland Ltd.; Pfizer Inc.; US2006/229352; (2006); 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. 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H19NO3

To a solution of PPh3 (240 mg, 0.91 mmol) in anhydrous THF (4 mL) was added DIAD (185 mg, 0.91 mmol) by syringe at 05 C, followed a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (185 mg, 0.91 mmol) in anhydrous THF (2 mL). The resulting mixture was poured into a solution of compound 308-5 (118 mg, 0.30 mmol) in dry THF (2 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: 3/1) to afford the title compound 309-15 as a yellow solid (300 mg).

According to the analysis of related databases, 153248-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (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. 34813-49-5, name is 2-Methylpropane-2-sulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 34813-49-5

Example 11.1N-{4-[(3,5-Dimethyl-4-{[(2-methylpropane-2-sulfonyl)carbamoyl]methyl}-1H-pyrazol-1-yl)methyl]phenyl}-4-(trifluoromethyl)benzamide{3,5-Dimethyl-1-[4-(4-trifluoromethyl-benzoylamino)-benzyl]-1H-pyrazol-4-yl}-acetic acid (example 1.1, 250 mg, 0.58 mmol), 2-methylpropane-2-sulfonamide (95 mg, 0.70 mmol), 1,3-dicyclohexylcarbodiimid (143 mg, 0.70 mmol) and 4-dimethylaminopyridine (85 mg, 0.70 mmol) in 2.5 ml dichloromethane were stirred for 3 h at 30 C. The solvent was removed under reduced pressure and the residue was purified by MPLC (silica gel, CH2Cl2/methanol 95:5).Yield: 51 mgESI mass spectrum: [M+H]+=551Retention time HPLC: 1.34 min (method D).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/28938; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 85175-59-3, name is 3-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one, molecular formula is C15H18ClNO3, 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: C15H18ClNO3

EXAMPLE 1 1-[7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4,-tetrahydronaphth-2-yl)-amino]-propane A mixture of 2-methylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene (1.72 g, 0.0078 mol), triethylamine (1.09 ml, 0.0078 mol) and 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloropropane (2.3 g, 0.0078 mol) is heated to a reaction temperature of 90 C. in steps within one hour and kept at this temperature for 2 hours. The initial suspension slowly changes into a clear solution and begins to precipitate in a jelly-like manner after about 30 minutes. The cooled reaction mixture is dissolved in 0.5M sodium hydroxide solution/ethyl acetate, the organic phase is washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over alumina (300 g), neutral, activity II, with methylene chloride and then with increasing quantities of ethanol (up to 20%). The hydrochloride is precipitated from a solution in acetone using ethereal hydrochloric acid. Yield: 1.39 g Mp: >125 C. (Decomp.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 85175-59-3, its application will become more common.

Reference:
Patent; Dr. Karl Thomae GmbH; US4584293; (1986); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 782-45-6, 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 782-45-6 as follows.

Stage 1: 4-[(2-chloro-9H-purin-6-yl]amino]-N-phenylbenzamide The procedure is carried out as in Example 1, starting with 195 mg of 2,6-dichloropurine, 5 ml of butanol and 272 mg of 4-amino-N-phenylbenzamide. 360 mg of the expected product are thus obtained.

According to the analysis of related databases, 782-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma S.A.; US2004/63732; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 209917-48-6, name is N-tert-Butyl 4-Aminophenylsulfonamide, 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 209917-48-6, Product Details of 209917-48-6

A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried. 2,5-Dichloro-/Y4-(4-[/Y-(l,l-dimethylethyl)sulfamoyl]phenyl)pyrimidin-4-amine (SG1-182): This was prepared from 2,4,5-trichloropyrimidine (0.500 g) and SG1-177 (0.715 g) using procedure A (stirred for 4 d). The crude solid was purified via flash chromatography (S1O2) eluting with hexanes/EtOAc (0: 10 to 4:6 v/v) to provide the title compound as a tangerine-colored solid (0.590 g, 58%). Mp: 180-181 C. NMR (400 MHz, DMSO-ifc): delta 9.73 (s, IH, disappeared on D20 shake), 8.46 (s, IH), 7.80 (s, 4H), 7.48 (s, IH, disappeared on D20 shake), 1.09 (s, 9H). HPLC-MS (ESI+): m/z 773.1 [10%, (MCl35Cl37+M35Cl35Cl+Na)+], 379.1 [10%, (MC137C137+H)+], 377.1 [70%, (MC135C137+H)+], 375.1 [100%, (M35C135C1+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, N-tert-Butyl 4-Aminophenylsulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); 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. 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H7N3O2S

General procedure: A mixture of alpha,beta-unsaturated aromatic or aliphatic acid (10 mmol), CH3SO2Bt (10 mmol) and Et3N (15 mmol) were refluxed in dry THF (50 mL) overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2 (100 mL). The organic phase was washed with brine (3 times) and dried over anhydrous Na2SO4. The organic phase was concentrated under vacuum to give a crude product, which could be further purified by recrystallization from a proper solvent.

The synthetic route of 37073-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xia, Ziming; Lv, Xin; Wang, Wencun; Wang, Xiaoxia; Tetrahedron Letters; vol. 52; 38; (2011); p. 4906 – 4910;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 94838-59-2, 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. 94838-59-2 name is tert-Butyl 4-aminophenethylcarbamate, 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 formaldehyde (0.303 g, 4 mmol, 40% in water), fert-butyl 4- aminophenethylcarbamate (1.135 g, 4.8 mmol) and NaBH3CN (1.257 g, 20 mmol) in methanol (14 mL) was stirred at room temperature for 4 h. Water (30 mL) was added to the reaction mixture afterward and the mixture was extracted with ethyl acetate (30 mL 3). The organic layer was washed with water (20 mL) and brine (20 mL), dried with NaiSCri and concentrated. The residue was purified by column chromatography to afford the title compound as colorless oil (0.337 g, 33.7 % yield). NMR (500 MHz, DMSO-riri) d: (d, J= 8.3 Hz, 2H), 6.79 (t, J= 5.3 Hz, 1H), 6.46 (d, J= 8.4 Hz, 2H), 5.41 (q, J= 5.0 Hz, 1H), 3.03 (dd, J= 14.9, 6.1 Hz, 2H), 2.64 (d, J= 5.2 Hz, 3H), 2.54 – 2.51 (m, 2H), 1.38 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-aminophenethylcarbamate, and friends who are interested can also refer to it.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics