Tag: M.W=200-300

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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 mixture of 29 (0.123 g; 0.27 mmol), 139 (0.063 g, 0.30 mmol), NaI (0.040g ; 0.27 mmol) and K2CO3 (0.045 g; 0.32 mmol) in dimethylacetamide (3 ml) was heated at [85C] under argon atmosphere for 3 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient [1-3%] of 3.5 N [NH3 IN MEOH/METHYLENE] chloride to give after trituration in ether/pentane Example 51 as a white solid. Yield: [78%] MS-ESI: 631 [[M+H] +] [1H NMR (CDC13)] : 1.31 (m, 6H); 1.45 (s, 9H); 1.50-1. 75 (m, 4H); 1.62 (s, 6H); 2.35 (s, 6H); 2.72 (m, 2H); 2.80 (m, 4H); 2.94 (m, 2H); 3.25 (br m, 2H); 3.55 (br m, 2H); 4.10-4. 20 (br m, 1H); 4.70-4. 80 (br m, 1H); 6.74 (s, 1H) ; 6.95 (s, 1H); 7.07 (s, 2H); 8.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); 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. 96-72-0, name is 2-Chloro-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H5ClN2O4S

The compound 4 (14.15 g, 59.8 mmol) and 300 mL of methanol were placed into a flask and stirred at 50 C until dissolved completely and then 10% Pd/C (1.4 g) was added. The mixture was intensively stirred under H2 at 50 C and monitored with TLC. After 4 h, the reaction was complete, and the suspension was filtered. The resulting solution was evaporated to give the crude product. It was dissolved in 30 mL of 9 mol/L hydrochloric acid solution and filtered. The filtrate was alkalified with 10 mol/L sodium hydroxide solution to pH 7. The suspension was filtered to afford the compound 5 (10.27 g, 83% yield, m.p. 166-167 C). 1H NMR (400 MHz, DMSO-d6) delta (ppm): 7.969 (d, 1H, JH = 8.8 Hz, Ar-H), 8.017 (s, 2H, SO2NH2), 8.414-8.442 (m, 1H, Ar-H), 8.671-8.677 (m, 1H, Ar-H).

According to the analysis of related databases, 96-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pan, Li; Jiang, Ying; Liu, Zhen; Liu, Xing-Hai; Liu, Zhuo; Wang, Gang; Li, Zheng-Ming; Wang, Di; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 18 – 26;,
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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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,1,1-Trifluoro-N-phenylmethanesulfonamide

6- (3-METHOXYPHENYL)-2- (2-MORPHOLIN-4-YL-2-OXOETHYL)-3-HYDROPYRIMIDIN-4-ONE 8 (leq) is dissolved in CH2CL2 in a round bottom flask, oven dried and kept under N2. Triethylamine is added (1.4 eq) followed by N-Phenyl trifluoromethanesulfonimide (1.2 eq) and DMAP (10 mol%). The reaction mixture is stirred at room temperature overnight. The solvent is evaporated under reduced pressure and the residue purified by chromatography on silicagel (ethyl acetate/hexanes 1: 5), obtaining the desired 6- (3-METHOXYPHENYL)-2- (2-MORPHOLIN-4-YL-2-OXOETHYL) pyrimidin-4-yl (trifluoromethyl) sulfonate 9.

According to the analysis of related databases, 456-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIRON CORPORATION; WO2004/48365; (2004); A1;,
Amide – Wikipedia,
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Related Products of 146651-75-4, A common heterocyclic compound, 146651-75-4, name is tert-Butyl (2-aminophenyl)carbamate, molecular formula is C11H16N2O2, 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.

Step 1: tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate (94)To solution of (2-amino-phenyl)-carbamic acid tert-butyl ester (22) (Seto, C. T.; Mathias, J. P.; Whitesides, G. M.; J. Amer. Chem. Soc., (1993), 115, 1321-1329.) (1.56 g, 7.49 mmol) in MeCN (40 mL) is added triethylamine (2.60 mL, 18.7 mmol) and 6-chloronicotinic acid (1.42 g 8.99 mmol). The mixture is stirred for 18 h at r.t. Upon completion of the reaction, the solvent is removed in vacuo and the residue is partitioned between EtOAc and an NH4Cl solution. The organic phase is collected and the aqueous layer is then extracted with EtOAc; the combined organic layers are washed with brine, dried over MgSO4 and evaporated. The residue is purified by flash chromatography using EtOAc/Hexane (a gradient of 20:80 to 50:50) as an eluent, to afford the title compound 94 (2.39 g, 92% yield). 1H NMR (DMSO-d6) delta (ppm): 10.01 (s, 1H), 8.96 (d, J=2.0 Hz, 1H), 8.71 (s, 1H), 8.35 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.22 (td, J=7.8, 1.4 Hz, 1H), 7.13 (t, J=7.6 Hz, 1H), 1.44 (s, 9H). LRMS (ESI): (calc) 347.10 (found) 370.1 (M+Na+).

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; METHYLGENE INC.; US2008/227826; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, 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 54616-47-6, Recommanded Product: 54616-47-6

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 ¡Á 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

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-Bromo-N,N-dimethylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
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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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C11H14FNO2

(4-Bromo-thiazol-2-yl)-(4-fluoro-phenyl)-carbamic acid tert-butyl ester; A mixture of (4-fluoro-phenyl)-carbamic acid tert-butyl ester (260 mg, 1.23 mmol), 2,4-dibromothiazole (100 mg, 0.41 mmol), copper powder (26 mg, 0.41 mmol), CuCl (41 mg, 0.41 mmol), and KOAc (40 mg, 0.41 mmol) in pyridine (4 ml) is heated at 1000C for 2 hours. The cooled mixture is diluted with EtOAc (30 ml) and washed with H2O (30 ml). The organic layer is dried over Na2SO4, filtered and concentrated in vacuum. The residue is purified by HPLC (C]8 column, eluted with CH3CN/H2O with 0.035% TFA) to give the title compound as solid: 1H NMR (DMSO-d6) delta 1.36 (s, 9H), 7.29 (t, 2H, J = 8.8 Hz), 7.37-7.43 (m, 3H); m/z [M+^t-Bu] 316.9.

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; IRM LLC; WO2007/16228; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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 2-(2,6-dioxopiperidin-3 -yl)-5-fluoroisoindoline- 1,3 -dione (3-1,100mg, 0.362mmo1, 1 equiv)inNMP(1.8mL, 0.2 M) was added DIPEA (126 jiL, 0.724mmol, 2 equiv) and tert-butyl (2-(2-aminoethoxy)ethyl)carbamate (74 mg, 0.362 mmol, 1 equiv). The reaction mixture was heated to 90 C overnight and then cooled to room temperature. EtOAc (50 mL) was added. The organic layer was washed with water (30 mL) and brine (3 x 30 mL), dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by flashcolumn chromatography on silica gel (eluting with 0 to 5% MeOH in CH2C12) to give the title compound 9-1 as a yellow solid (37 mg, 22%). ?H NIVIR (500 MHz, CDC13) 8.70 (s, 1H), 7.607.47 (m, 1H), 6.99 – 6.85 (m, 1H), 6.74 (d, J= 8.3 Hz, 1H), 5.06 -4.96 (m, 1H), 4.92 (dd, J= 12.0, 5.3 Hz, 1H), 3.72 – 3.63 (m, 2H), 3.58 – 3.48 (m, 2H), 3.33 – 3.24 (m, 4H), 2.95 – 2.66 (m, 3H), 2.09 (ddd, J= 10.5, 6.6, 3.2 Hz, 1H), 1.43 (s, 9H). MS (ESI) [M+H]: 461.2.

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 (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; BUCKLEY, Dennis; ISHOEY, Mette; WINTER, Georg; (195 pag.)WO2018/98280; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 579474-47-8, 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. 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-(8-Fluoro-2-oxo-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)picolinonitrile (1b). tert-Butyl (2-amino-4-fluorophenyl)carbamate (0.226g, 1mmol) and tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate (0.320g, 1.3mmol) were dissolved in toluene (5mL) and heated at reflux for 1h. The reaction mixture was cooled and the excess solvent was removed under reduced pressure. The crude intermediate was taken up in CH2Cl2 and TFA (1.14g, 10mmol) was added dropwise to it at 0C. The resulting reaction mixture was stirred at rt for 7h. The crude mixture was washed with sodium bicarbonate solution and the aqueous layer extracted with CH2Cl2. The combined organic layers were washed with water, then brine, and dried over Na2SO4. Evaporation of the solvent followed by column chromatography using hexanes:ethyl acetate (60:40) yielded the title compound.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-amino-4-fluorophenylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dhanya, Raveendra Panickar; Herath, Ananda; Sheffler, Douglas J.; Cosford, Nicholas D.P.; Tetrahedron; vol. 74; 25; (2018); p. 3165 – 3170;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6292-59-7, 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. 6292-59-7 name is 4-(tert-Butyl)benzenesulfonamide, 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.

Step-A: 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyridinyl]benzene sulfonamide potassium salt (potassium salt of (IV)) 4,6 dichloro-5-(2-methoxybenzyl)-2,2-bipyrimidine (II) (100 g, 0.286 moles) and anisole (1250 ml) were placed in a reaction flask. Potassium carbonate (79 g, 0.572 moles) was added and reaction mass was stirred for 15 minutes. 4-tert-butylbenzenesulphonamide (III) (213 g, 0.286 moles) was added to reaction mass and heated to 140 C. for three hours. After completion of reaction the reaction mass was brought to room temperature and poured into purified water. The solid product was filtered off, washed with THF and dried to afford 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyridinyl]benzene sulfonamide potassium salt. (161 g, yield 96.2% , purity by HPLC: 99.7%)

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

Reference:
Patent; Natco Pharma Limited; Kompella, Amala Kishan; Kasa, Srinivasu; Balina, Veera Swamy; Kusumba, Subhash; Adibhatla, Kali Satya Bhujanga Rao; Nannapaneni, Venkaiah Chowdary; US2013/245259; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 5577-13-9, A common heterocyclic compound, 5577-13-9, name is Ethyl tosylcarbamate, molecular formula is C10H13NO4S, 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.

General procedure: A solution of ethyl (phenylsulfonyl) carbamate (1.2 mmol, 18a-d) in toluene (5 mL) was addeddropwise to a solution of 8a-d or 14a-d (1 mmol) in toluene (15 mL). Upon completion of the addition,the reaction mixture was stirred at 120 C for 6 h and monitored by thin-layer chromatography (TLC).The reaction mixture was cooled to room temperature and concentrated under a reduced pressure.Then, ethyl acetate was added and the insoluble materials were collected by filtration and driedto yield the target compounds 19a-d, 20a-d, 21a-d, 22a-d and 23a-d, which were recrystallizedfrom isopropanol.

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; Zhao, Bingbing; Lei, Fei; Wang, Caolin; Zhang, Binliang; Yang, Zunhua; Li, Wei; Zhu, Wufu; Xu, Shan; Molecules; vol. 23; 7; (2018);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics