Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 87905-98-4, name is Benzyl (5-hydroxypentyl)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 87905-98-4, category: amides-buliding-blocks

To a solution of oxalyl chloride (814 mul, 9.62 mmol, 2.3 equiv.) in dried dichloromethane (25 ml) under an inert atmosphere was slowly added a solution of dimethylsulfoxyde (1.3 ml, 18.2 mmol, 4.3 equiv.) in dried dichloromethane (10 ml). The solution was stirred for 5 min at -70C then a suspension of benzyl ((5-hydroxypentyl)carbamate) [21] (1 g, 4.22 mmol, 1 equiv.) in dried dichloromethane (25 ml) was transferred via canula. The mixture was stirred for 25 min at -70C then triethylamine (11.7 ml, 8.44 mmol, 20 equiv.) was slowly added. The reaction mixture was stirred for 20 min at -70C and 15 min at room temperature and then quenched by addition to 600 ml of water. The aqueous phase was extracted with diethylether (3×100 ml) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the aldehyde (1.1 g) used in the next step without purification. To a suspension of potassium cyanide (249 mg, 3.83 mmol, 1 equiv.) in water (520 mul) were added ammonium chloride (203 mg, 3.83 mmol, 1 equiv.) and ammonium hydroxide 33% (1.32 ml; 20.3 mmol, 5.3 equiv.). The reaction mixture was stirred for 15 min at 0C then a solution of the aldehyde (900 mg, 3.83 mmol, 1 equiv.) in dioxane (1.35 ml) was added dropwise over 20 min. The mixture was stirred for 20 h and then quenched by addition of water (10 ml) and diethyl ether (30 ml). The aqueous phase was acidified with HCl 1 M (50 ml), washed with diethyl ether (3×20 ml), basified to pH = 12 with NaOH 1 M (20 ml) and then extracted with dichloromethane (4×10 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the protected aminonitrile; yield: 905 mg (91%). 1H NMR (MeOD-d4, 300 MHz) delta 1.52 (m, 4H, H4, H5), 1.71 (m, 2H, H3), 3.14 (t, 2H, H6), 3.71 (t, 2H,H2), 5.06 (s, 2H, H8), 7.34 (m, 5H, H10-H12); 13C NMR (MeOD-d4, 75 MHz) . 23.9 (C4), 30.4 (C5), 35.9 (C3), 41.5 (C6), 44.2 (C2), 67.4(C8), 123.1 (C1), 128.8-129.6 (C10-C12), 138.6 (C9), 159.0 (C7) (seeSI, Figs. S3 and S4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (5-hydroxypentyl)carbamate, and friends who are interested can also refer to it.

Reference:
Article; Bordier, Franck; Stam, Mark; Darii, Ekaterina; Tricot, Sabine; Fossey, Aurelie; Rohault, Johanna; Debard, Adrien; Mariage, Aline; Pellouin, Virginie; Petit, Jean-Louis; Perret, Alain; Vallenet, David; Salanoubat, Marcel; Weissenbach, Jean; Vergne-Vaxelaire, Carine; De Berardinis, Veronique; Zaparucha, Anne; Journal of Molecular Catalysis B: Enzymatic; vol. 107; (2014); p. 79 – 88;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 72505-21-6, 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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Appropriate thiobenzamides or thioacetamides (1 mmol) and alpha-chloroacetoacetate 3 (150 mg, 1.2 mmol) were added to absolute ethanol (15 mL). The reaction mixture was heated at reflux for 24 h. After removal of solvent under reduced pressure, the residue was purified by silica gel chromatography using hexanes-ethyl acetate (7:3) to provide the desired compounds.

The synthetic route of 4-(Trifluoromethyl)thiobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mayhoub, Abdelrahman S.; Khaliq, Mansoora; Botting, Carolyn; Li, Ze; Kuhn, Richard J.; Cushman, Mark; Bioorganic and Medicinal Chemistry; vol. 19; 12; (2011); p. 3845 – 3854;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 51-06-9, 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. 51-06-9 name is 4-Amino-N-(2-diethylaminoethyl)benzamide, 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 p-SCN-Bn-NOTA (0.05 g, 0.09 mmol) and 4-amino-N-(2-(diethylamino)ethyl)benzamide (0.030 g, 0.11 mmol) in CHCl3 (1 mL) containing TEA (45 muL, 0.27 mmol) was stirred 24 h at room temperature. The solvent was evaporated under reduced pressure. The resulting product was purified by semi-preparative HPLC (gradient 10% of H2O for 5 min and 10-70% of MeCN for 30 min; flow rate, 2 mL/min; 240 nm; tR, 12 min) to give SCN-NOTA-BZA as a pale yellow solid (46 mg, 75%). MS (FAB) m/z 686, (M+H)+; HRMS of C33H48N7O7S 686.3336 (calculated) and 686.3340 (observed); 1H NMR (500 MHz, D2O): delta 7.68 (d, 1H), 7.34 (d, 2H), 7.20 (m, 4H), 3.67-3.65 (br, 2H), 3.54-3.50 (br, 2H), 3.39-3.29 (br, 4H), 3.20-3.12 (br, 6H), 3.09-2.99 (br, 8H), 2.92-2.52 (br, 3H), 1.20-1.14 (br, 8H); 13C NMR (125 MHz, D2O): delta 179.3, 178.5, 176.3, 174.4, 169.8, 142.0, 136.8, 136.1, 130.3, 130.0, 129.8, 128.8, 128.2, 126.0, 125.6, 124.5. 60.6, 57.8, 57.6, 57.2, 57.1, 52.4, 52.1, 51.6, 50.6, 47.6, 46.6, 46.0, 43.5, 34.9, 33.7, 33.6, 8.2, 8.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-(2-diethylaminoethyl)benzamide, and friends who are interested can also refer to it.

Reference:
Article; Kim, Hee-Jung; Kim, Dong-Yeon; Park, Jeong-Hoon; Yang, Seung-Dae; Hur, Min-Goo; Min, Jung-Joon; Yu, Kook-Hyun; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 4915 – 4920;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

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; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
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. 97308-23-1, name is tert-Butyl aziridine-1-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 97308-23-1

Step 4 To the solution tert-butyl aziridine-1-carboxylate LXXXVI (excess) in dioxane was added (2-aminioethyl)trimethylazanium dichloride LXXXIV (0.25 g; 1.8 mmol). The mixture was refluxed for 3 days. The solvent was removed under reduced pressure and the residue was purified on a silica gel column (100:1 CHCl3:MeOH) to give crude tert-butyl N-(2-{[2-(trimethylaminio)ethyl]amino}ethyl)carbamate chloride LXXXVII was used directly for step 5.

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; Mpex Pharmaceuticals, Inc.; US2008/318957; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 138-41-0, name is Carzenide, molecular formula is C7H7NO4S, 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. name: Carzenide

A. 4-Sulfamoyl-benzoic acid methyl ester. To a stirred suspension of 4-sulfamoyl-benzoic acid (25.0 g, 0.124 mol) in 4:1 CH2Cl2/MeOH at rt was added 1.0 M TMSCHN2 in hexane (175 mL), and the reaction mixture was allowed to stir for 2 h. The mixture was diluted with 1 N NaOH (100 mL) and CH2Cl2 (150 mL), and the layers were separated. The organic layer was dried over Na2SO4, then filtered, and the solvent was removed under reduced pressure to afford the desired ester (25.2 g, 95%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 8.14 (d, J=8.1 Hz, 2H), 7.96 (d, J=8.1 Hz, 2H), 7.58 (s, 2H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138-41-0, its application will become more common.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 107017-73-2, These common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, 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.

4-(3-(4-Hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluor omethyl)benzonitrile 14c (100 mg, 0.25 mmol) was placed in a reaction flask, followed by addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 6a (93 mg, 0.49 mmol), triphenylphosphine (97 mg, 0.37 mmol), 5 mL of dichloromethane and diisopropyl azodicarboxylate (75 mg, 0.37 mmol) successively. The reaction solution was stirred for 2 hours. The reaction solution was concentrated under the reduced pressure and the residue was purified by thin layer chromatography with elution system A to obtain the title compound tert-butyl (1-((4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin -1-yl)phenoxy)methyl)cyclopropyl)carbamate 37a (50 mg, yield 35.2%) as a white solid. MS m/z (ESI): 519.3 [M-56+1]

Statistics shows that tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 107017-73-2.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; Jiangsu Hengrui Medicine Co. Ltd.; LU, Hejun; SUN, Piaoyang; FEI, Hongbo; JIANG, Hongjian; WANG, Haowei; DONG, Qing; EP2894151; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 406233-31-6 as follows. name: 4-Fluoro-3-nitrobenzenesulfonamide

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

According to the analysis of related databases, 406233-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, molecular formula is C10H11F2NO4S, 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. Product Details of 1103234-56-5

Triethylamine (4.68 mL, 33.59 mmol) and diphenylphosphonic azide (3.73 mL, 16.79 mmol) were added to a solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (4.078 g, 14.6 mmol) in THF (60 mL). The reaction mixture was stirred at room temperature for 3 hours and then warmed to 80C for 2 hours. Water (10 mL) was added, and the mixture was stirred at 80C for 15 hours. The reaction mixture was diluted with EtOAc (300 mL), and the organic layer was washed with saturated aqueous NaHC03 solution and brine. The solvent was removed under reduced pressure, and the residual purified via silica gel column chromatography eluting with 30/70 EtOAc/hexane to obtain 2.03 g (55%) of the title compound. 1H NMR (400 MHz, DMSO-d6) delta 9.32 (s, 1H), 6.90-^.80 (m, 1H), 6.51 (td, J=8.7, 5.5, 1H), 5.28 (s, 2H), 3.05-2.96 (m, 2H), 1.82-1.64 (m, 2H), 1.01-0.90 (m, 3H). LC/MS: w/z 251.1 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1103234-56-5, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 579474-47-8, These common heterocyclic compound, 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, 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 solution of 0110-31 (200 mg, 0.4 mmol), TBTU (200 mg, 0.6 mmol), N1, Lambdaf2-diisopropylethane-l, 2-diamine (364 mg, 2.82 mmol), and tert-butyl 2-amino-4- fluorophenylcarbamate (0113-60) (90 mg, 0.4 mmol) in DMF (4 mL) and THF (2 mL) was stirred at r.t. for 3 hours. Then DMF and THF were removed under reduced pressure and the residue was dispensed in water and filtered to get the crude product. The crude compound was further purified by flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford pure product tert-butyl 2-(4- (4-(2-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-ylamino)-2- oxoethyl)phenoxy)butanamido)-4-fluorophenylcarbamate (150 mg, 54%) as a pale yellow solid. LCMS : 698 [M+ 1 ]+.

Statistics shows that tert-Butyl 2-amino-4-fluorophenylcarbamate is playing an increasingly important role. we look forward to future research findings about 579474-47-8.

Reference:
Patent; CURIS, INC.; QIAN, Changgeng; CAI, Xiong; ZHAI, Haixiao; WO2010/75542; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics