Amides-buliding-blocks

Some common heterocyclic compound, 1092522-02-5, name is tert-Butyl (4-aminophenyl)(methyl)carbamate, 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. HPLC of Formula: C12H18N2O2

General procedure: HBTU (1.82g, 3.59mmol), DIPEA (0.84mL, 4.80mmol) and monomethyl suberate (0.93mL, 5.28mmol) were added to a solution of 34 (1.0g, 4.80mmol) in DMF (10mL) and the mixture was stirred for 12hat rt. Then the reaction was quenched with H2O and extracted using EtOAc, dried over MgSO4 and passed through a filter column to give corresponding ester which was dissolved in the minimum amount of dioxane. H2O with pH adjusted to 3 using 3N HCl was added and the reaction mixture was stirred at reflux overnight to yield the corresponding free amine. The reaction was basified and extracted using EtOAc, then dried, concentrated and passed through a filter column to give the free amine. To a solution of this free amine (1.0g, 3.59mmol) in DMF (10mL) was added HBTU (1.36g, 3.59mmol), DIPEA (0.66mL, 3.59mmol) and 1,4-dibenzyloxy-5-isopropyl benzoic acid (0.76g, 4.31mmol) and the solution was stirred for 12hat 80C. The reaction mixture was quenched with H2O and extracted with EtOAc (25mL¡Á3). The combined organic layer was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a light yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1: 1) to give 42 as a colorless liquid in 65% yield (overall from 34)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1092522-02-5, its application will become more common.

Reference:
Article; Mehndiratta, Samir; Lin, Mei-Hsiang; Wu, Yi-Wen; Chen, Chun-Han; Wu, Tung-Yun; Chuang, Kuo-Hsiang; Chao, Min-Wu; Chen, Yi-Ying; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, 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 121492-06-6, name: N-Boc-(2-Aminoethyl)-N-methylamine

EXAMPLE H-l 4 Example H-14 N-ethyl-N-(2-((4-(2-hvdroxypropan-2-yl)pyrinudin-2-yl)(methyl)aniino)ethyl)-2- isopropoxynicotinamide Step 1 : tert-butyl (2-(((benzyloxy)carbonyl)amino)ethyl)(methyl)carbamate (H-7) To a solution of tert-butyl (2-aminoethyl) (methyl)carbamate (5.0 g, 28.7 mmol) in THF (100 mL) was added NaHC03 (12.1 g, 143.5 mmol) at 0 C. The resulting mixture was stirred at the same temperature for 15 min. Cbz-Cl (5.9 g, 34.4 mmol) was added dropwise. The mixture was stirred at RT overnight, then filtered and the filtrate was concentrated in vacuo. The residue was purified by combiflash (10% EtOAc in petroleum ether) to give the title compound H-7. LRMS m/z (M+H) 309.1found, 309.4 required.

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; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
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Related Products of 16695-22-0, A common heterocyclic compound, 16695-22-0, name is (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate), molecular formula is C25H29NO8S3, 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.

In a 50 ml three-neck bottle are sequentially added myricitrin in (509 mg, 1 . 6mmol), DMF (15 ml), K2CO3(276 mg, 2 . 0mmol), heating to 110 C, and then is slowly dripped N, N-bis [2 – (P-sulfonyloxy) ethyl]-P-toluene sulfonamide (454 mg, 0 . 8mmol) solution of DMF (15 ml), constant temperature 110 C reaction 3-5h (TLC tracking of the reaction, developing agent is petroleum ether (PE): ethyl acetate (EA): formic acid (HCOOH) =10:10:1, v/v), the reaction solution is poured into the acetic acid ethyl ester (30-60mL) in, filtered, concentrated under reduced pressure to get the crude product, the crude product by silica gel chromatography purification column or half preparation HPLC method, drying, HTEMY obtained compound (402 mg). The preparation method of this invention has the synthetic steps are simple, low cost, mild condition, and the like.

The synthetic route of 16695-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo Institute of Technology, Zhejiang University; Gao, Kun; Wu, Yuechan; Chen, Jia; (9 pag.)(2016);,
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Application of 106984-09-2, 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. 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium hydride (7.2 g, 0.3 mol) was weighed in a three-necked flask,Add 200 ml of tetrahydrofuran, cool to 0 or less,BOC-NH-PEG4 (29.3 g, 0.1 mol) was slowly added dropwise,Control the reaction temperature is about 0 . After 1 hour, continue to cool to -5 ,Slowly dropwise 3-bromopropionic acid (15.3 g, 0.1 mol) was added to control the reaction below 0 ,After the completion of the reaction at room temperature for 24 hours, with dilute hydrochloric acid PH value of 3-4,Ethyl acetate was extracted three times, the combined extracts were dried,Boc-NH-PEG4-CH2CH2COOH (23 g yield 63%) was recovered under reduced pressure.Boc-NH-PEG4-CH2CH2COOH (7.3 g, 0.020 mol) was dissolved in 50 mL of tetrahydrofuran,Slowly add 2mol / L hydrochloric acid solution (20mL),And stirred at room temperature overnight. The next day, add 50mL of ethyl acetate,And then extracted with ethyl acetate water phase once,The water phase evaporated to dry NH2PEG4-CH2CH2COOH hydrochloride crude,And then crystallized from ethyl acetate to give pale yellow crystals(3.92 g, Yield: 65%)

The synthetic route of tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Furuikang Biological Technology Co., Ltd.; Luo Qiandong; Hu Deyin; (7 pag.)CN104774161; (2017); B;,
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Application of 94838-59-2, These common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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.

A mixture of 3-(4-methylpiperazin-l-yl)propanoic acid (172 mg, 1 mmol), HATU (456 mg, 1.2 mmol), DIPEA (323 mg, 2.5 mmol) and /ert-butyl 4-aminophenethylcarbamate (236 mg, 1 mmol) in DCM (10 mL) was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (90mg, 23.0% yield). NMR (500 MHz, DMSO-riri) S: 10.01 (s, 1H), 7.48 (d, J= 8.4 Hz, 2H), 7.10 (d, J= 8.4 Hz, 2H), 6.84 (dd, J= 13.1, 6.9 Hz, 1H), 3.10 (dd, J= 14.1, 6.4 Hz, 2H), 2.64 (dd, .7= 24.9, 17.1 Hz, 6H), 2.45 (dd, J= 15.8, 8.8 Hz, 8H), 2.20 (d, J= 12.1 Hz, 3H), 1.37 (d, J= 1.6 Hz, 9H).

The synthetic route of 94838-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
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Application of 4141-08-6, 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. 4141-08-6, name is 2-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Dissolve 2-amino-N-methylbenzamide (1.26g, 8.4mmol) and 2,4-dichloro-5-methylpyrimidine (0.93ml, 8mmol) in anhydrous DMF (6ml) under ice bath 60% NaH (0.38g, 9.6mmol) was added and stirred at room temperature for 24h. After the end, water was added dropwise to terminate the reaction, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by silica gel column (eluted with ethyl acetate / petroleum ether) to obtain 0.88 g of yellow solid with a yield of 40%.

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

Reference:
Patent; Beijing Xibo Pharmaceutical Co., Ltd.; Yin Yuxin; Su Yue; (37 pag.)CN111072571; (2020); A;,
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Synthetic Route of 1268810-09-8, 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. 1268810-09-8, name is tert-Butyl (1-ethynylcyclopropyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

tert-Butyl (1-ethynylcyclopropyl )carbamate (200.0 mg, 1.104 mmol) was treated with azidotrimethyl silane (508.6 mg, 4.414 mmol, 4 equiv.) in the presence of copper iodide (21.0 mg, 0.11 mmol) in N,N-dimethylformamide (1 mL) and methanol (1 mL) and stirred at 110 C for 2 h. After cooling, purification by prep HPLC gave fert-butyl (1-(1H-1,2,3- triazol-4-yl)cyclopropyl)carbamate. LCMS-ESI+ (m/z): [M+H] + calculated for C10H17N4O2: 225.1 ; found: 225.1 .

The synthetic route of tert-Butyl (1-ethynylcyclopropyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; GUTIERREZ, David A.; KOBAYASHI, Tetsuya; LAZERWITH, Scott E.; LEE, Rick A.; MORGANELLI, Philip A.; PYUN, Hyung-Jung; (0 pag.)WO2019/165374; (2019); A1;,
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Amide – an overview | ScienceDirect Topics

Reference of 63920-73-0, The chemical industry reduces the impact on the environment during synthesis 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, I believe this compound will play a more active role in future production and life.

To a solution of 2-amino-4,6-dimethoxy-benzamide (7.50 g, 38.2 mmol) and 3-(2-hydroxy-ethoxy)-5-methoxy-benzaldehyde (7.50 g, 38.2 mmol) in N,N-dimethylacetamide (30 mL) was added NaHSO3 (58.5 wt %, 4.37 g, 42.0 mmol) and p-TSA (0.72 g, 3.8 mmol). The reaction mixture was heated to 115-120 C. for 16 hours, and then cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure, the residue was diluted with water (50 mL), and the solid was filtered, collected, and mixed with ether (50 mL), then filtered and dried under vacuum, to give 2-[3-(2-hydroxy-ethoxy)-5-methoxy-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one as a white solid. Yield: 10 g (70%).

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, 2-Amino-4,6-dimethoxybenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141449-85-6,Some common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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.

Reference Example 35: 5-(4-ChIoro-6-morphoIin-4-vI-pyrimidin-2-vImethyl)- hexahydro-pyrroloP.lambda-cipyrrole^-carboxylic acid tert- butyl ester; To a solution of 4-(2-bromomethyl-6-chloro-pyrimidin-4-yl)-morpholine (230 mg,0.786 mmol) in DMF (10 mL) were added potassium carbonate (212 mg, 1.53 mmol) and hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (250 mg, 1.18 mmol). The mixture was stirred at RT for 30 min. The reaction mixture was diluted with water then extracted into EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a colourless oil (332 mg, 100 %). [M + H]+ 424.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, its application will become more common.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125833; (2008); A1;,
Amide – Wikipedia,
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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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 108468-00-4

HOBT (1.45 g, 10.9 mmol) is added to a solution of {3-[3-(3-carboxymethoxyprop-1-ynyl)phenyl]prop-2-ynyloxy}acetic acid (A30, 0.40 g, 1.3 mmol) and 4-N-tert-butoxycarbonylaminomethylbenzylamine (1.2 g, 5.2 mmol) in absolute CH2Cl2 (20 ml) and Et3N (2.5 ml), and the mixture is stirred at RT for 45 min. EDC (2.1 g, 10.9 mmol) is then added, and the mixture is stirred at RT overnight. The reaction solution is diluted with CH2Cl2 (15 ml) and extracted (2¡Á) with semisaturated aqueous NH4Cl solution (25 ml), dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [Tol/Ac (8:2)] over a silica gel column gives the title compound (1.1 g) as a colorless powder. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.51.MS: calc.: C42H50N4O8 (738.0), found: [MH+] 738.8, [MNH4+] 755.8; [MNa+] 761.2

The synthetic route of 108468-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Altana Pharma AG; US6960588; (2005); B1;,
Amide – Wikipedia,
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