Month: July 2021

Reference of 183059-24-7, 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. 183059-24-7 name is tert-Butyl 2-hydroxy-2-methylpropylcarbamate, 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.

2,2-dimethyloxirane (0.1 g, 1.388 mmol) was added dropwise to 20 mL icecooled solution of ammonium hydroxide. The reaction mixture was stirred for 12 hours at roomtemperature. The solvent was removed under vacuum and the residue was dissolved inmethanol. Di-tert-butyl dicarbonate (0.75 g, 3.47 mmol) was added to the reaction mixture and15 stirred for 4 hours. The mixture was purified using column chromatography (24%EtOAc/hexane) to obtain tert-butyl 2-hydroxy-2-methylpropylcarbamate. The pure tert-butyl 2-hydroxy-2-methylpropylcarbamate was dissolved in 5 mL of trifluoroacetic acid and stirred for35 minutes. The solvent was removed under reduced pressure to afford 1-amino-2-methylpropan-2-ol as the trifluoroacetate salt 1′. 1H NMR 500 MHz (500 MHz, CDC13, 8 in20 ppm): 8 8.62 (s, 2H), 3.02 (d, 2H), 2.06-2.04 (m, 2H), 1.37-1.34 (s, 6H).

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

Reference:
Patent; PURDUE RESEARCH FOUNDATION; ENDOCYTE, INC.; LOW, Philip Stewart; WANG, Bingbing; LEAMON, Christopher Paul; LU, Yingjuan J.; WHEELER II, Leroy W.; (102 pag.)WO2017/205661; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 25900-61-2, 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. 25900-61-2 name is 3-Amino-N-methylbenzamide, 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 1To 4,6-dichloropyrimidine (500.0 mg, 3.36 mmol) and 3-amino-N-methylbenzamide (504 mg, 3.36 mmol) in 2-propanol (5.00 mL) at RT was added N,N-diisopropylethylamine (0.877 mL, 5.03 mmol). The resulting reaction mixture was heated at 80 C for 3 days, cooled to RT, concentrated, purified using MPLC (25 g cartridge, 40 g column, 0 to 100% EtOAc- hexanes then 30-100% 90: 10 CH2Cl2-MeOH in CH2C12). Fractions with product were combined and concentrated giving 3-(6-chloropyrimidin-4-ylamino)-N-methylbenzamide (815.2 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-N-methylbenzamide, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin, F.; DU, Bingfan; NGUYEN, Hanh, Nho; ZHENG, Xiao, Mei; WO2011/103196; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 143557-91-9, A common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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 tert-butyl (3-endo)-3-hyd roxy-8-azabicyclo[3.2.1 ]octane-8-carboxylate (3g, 13.20 mmol, combi-blocks) in THF (30 mL) was added portion wise potassium tertbutoxide (1.6 g, 14.5 mmol). The reaction was then refluxed for lh. The reaction was removed from the oil bath and 1-bromo-2,4-difluoro-benzene (1.6 mL, 14.52 mmol, Matrix) was added. The reaction was again refluxed for 1 .5h and cooled to RT. Ethyl acetate was added. The layers were separated and the organic layer was washed withwater, brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude was purified by flash chromatography using 5% ethyl acetate in cyclohexane to give a colourless oil that crystallised upon standing (4.1 g, 79%). 1H NMR (400 MHz, DMSOd 6): 67.63-7.59 (m, 1H), 6.98 (dd, J1= 11.40, J2= 2.76 Hz, 1H), 6.76-6.71 (m, 1H), 4.81 (t, J= 4.40 Hz, 1H), 4.06 (s, 2H), 2.15-2.05 (m, 4H), 1.87-1.84 (m, 4H), 1.41 (s, 9H).LCMS: (Method A) 344.0 (M-?Bu-f-H), Rt. 6.2 mm, 84.9% (Max).

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; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; MURUGESAN, Kathiravan; BANERJEE, Joydeep; WO2014/198808; (2014); 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 631-58-3 as follows. name: Propanethioamide

0.40 g (1 .47 mmol) 5-bromo-azepan-4-one hydrobromide, 0.13 g (1 .47 mmol) thiopropionamide and 3 mL ethanol. were stired under reflux for 3 hours. The reaction was allowed to cool to RT and was filtered. The filtrate was concentrated to dryness and dried. Yield: 0.39 g (quantitativ) ESI-MS: m/z = 183 (M+H)+ Rt(HPLC): 0.39 min (Method J)

According to the analysis of related databases, 631-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GOTTSCHLING, Dirk; EBEL, Heiner; RIETHER, Doris; WELLENZOHN, Bernd; WO2013/144172; (2013); 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. 24167-56-4, name is 4-Fluoro-N,N-dimethylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Fluoro-N,N-dimethylbenzamide

General procedure: Oxalyl chloride (1.0 equiv) was added dropwise at r.t. (except in synthesis of 4e, where addition was at 0 C) to the corresponding N,N-dialkylbenzamide 1 (1.0 equiv) in anhydrous CH2Cl2 (1.0 mL/mmol 1) under N2 atmosphere. The reaction mixture was heated at 35 C for 5 h. Generally, a white solid was observed after few minutes. When the reaction was finished, anhydrous CH2Cl2 was added (4.0 mL/mmol 1) at 0 C; usually at this temperature the solid dissolved. A solution of trichloroacetamidine 2 (1.0 equiv) in anhydrous CH2Cl2 (1.0 mL/mmol 2) was added dropwise at 0 C. Immediately a white suspension formed, and the reaction mixture was stirred overnight at r.t. Finally, DIPEA (2.2 equiv) was added at 0 C; a pale yellow solution resulted. CH2Cl2 (20 mL) was added and the organic phase was washed with saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo. The resulting crude 1,3-diazabutadiene 4 was obtained in quantitative yield, usually contaminated with small quantities of starting material as an oil that slowly crystallized. The 1,3-diazadienes 4 were purified by flash column chromatography (silica gel, hexanes-EtOAc). After purification, 1,3-diazadienes 4 were obtained as crystals or as oils.

According to the analysis of related databases, 24167-56-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seballos-Resendiz, Arturo; Lechuga-Eduardo, Harim; Barroso-Flores, Joaquin; Martinez-Otero, Diego; Romero-Ortega, Moises; Synthesis; vol. 48; 14; (2016); p. 2205 – 2212;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 42137-88-2,Some common heterocyclic compound, 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, molecular formula is C11H15Cl2NO2S, 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 (R)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-amine (2 g, 12.1 mmol) in DIPEA (4.22 mL, 24.2 mmol), N,N-bis(2-chloroethyl)-p-toluene sulfonamide (3.9 g, 13.3 mmol) was added at rt and the resulting mixture was heated to 105 C for 18 h. Completion of the reaction was confirmed by TLC. Reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layer was dried over Na2SO4 and evaporated under vacuum. To the resulting crude solid hexane (50 mL) was added, and the resulting mixture was stirred for 10 min at rt. It was filtered and the solid was washed with Et2O (2 x 50 mL) and dried under vacuum to give the title compound. Yield: 63.8% (3 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.59 (d, J = 8.4 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 6.81-6.77 (m, 2H), 6.69-6.6 (m, 1H), 5.97-5.95 (m, 2H), 3.35-3.31 (m, 1H), 2.81-2.80 (m, 4H), 2.42 (s, 3H), 2.36-2.32 (m, 4H), 1.18 (d, J= 6.8 Hz, 3H). LCMS: (Method A) 389.0 (M+H), Rt. 3.39 min, 98.9% (Max). HPLC: (Method A) Rt. 3.30 min, 99.53% (Max), Chiral HPLC: (Method A) Rt. 15.54 min, 97.58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 683-57-8, name is 2-Bromoacetamide, 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 683-57-8, HPLC of Formula: C2H4BrNO

A flask was charged with 4-cyano-lH-imidazole-2-carboxylic acid (2-cyclohex-l- enyl-4-piperidin-4-yl-phenyl)-amide TFA salt (50 mg, 0.10 mmol) (as prepared in Example 14, step (b)), NEt3 (32 muL, 0.23 mmol), 2-bromoacetamide (16 mg, 0.12 mmol), and 0.5 mL of DCM and stirred for 4 h at 25 0C. The reaction was concentrated and the title compound was purified by RP-EtaPLC (C 18), eluting with 30-50 % CH3CN in 0.1 % TFA/H2O over 12 min to give 42 mg (75 %) of a white solid. 1H-NMR (400 MHz, DMSO-d6): delta 14.28 (br s, IH), 9.78 (s, IH), 9.50 (br s, IH), 8.34 (s, IH), 8.00 (s, IH), 7.88 (d, IH), 7.72 (s, IH), 7.18 (dd, IH), 7.10 (d, IH), 5.76 (m, IH), 3.94 (s, 2H), 3.58 (m, 2H), 3.12 (m, 2H), 2.80 (m, IH), 2.20 (m, 4H), 1.98 (m, 4H), 1.80 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C24H28N6O2, 433.2 (M+H), found 433.2.

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; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)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 127828-22-2, category: amides-buliding-blocks

A solution of 6-chloro-4-hydroxy-5-methyl-3-nitropyridin-2(iH)-one (10.9 g, 53.4 mmol) in dichloromethane (380 mL) was cooled to 0 C. Triethylamine (22.3 mL, 160 mmol) was added, and the solution was stirred for ten minutes. Trifluoromethanesulfonic anhydride (18.0 mL, 107 mmol) was then added dropwise over a period of five minutes, and the solution was stirred for 1.5 hours at 0 C. A solution of tert-butyl 2-(2-aminoethoxy)ethylcarbamate (12.0 g, 58.8 mmol), prepared as described in Parts A through D of Example 102, in a small amount of dichloromethane was then added over a period of five minutes, and the reaction was allowed to warm to room temperature slowly and stirred overnight. The solution was then washed with water (2×150 mL) and brine (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting sequentially with 80:20 hexanes:ethyl acetate and 50:50 hexanes:ethyl acetate) to provide a yellow oil, which was dissolved in diethyl ether and concentrated under reduced pressure to provide 16.5 g of trifluoromethanesulfonic acid 4-[(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl)amino]-6-chloro-5-methyl-3-nitropyridin-2-yl ester as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl-N-(tert-butoxycarbonyloxy) carbamate (224 mg, 0.96 mmol) in DMF (2 [MNo.) ] was reacted with sodium hydride (38 mg, 0.96 mmol) at [0 C] and stirred for 20 mins at room temperature. The reaction mixture was treated by dropwise addition of benzyl [N- [4- (BROMOMETHYL)-2-FLUOROPHENYL]] carbamate compound 52 (250 mg, 0.74 mmol) and stirred for 1 hour. After concentrating, residual mixture was purified by column chromatography on Silica gel with EtOAc/hexanes (1: 5) solvent mixture as an eluant to give 355 mg of yellow oil of tert-butyl [N-[(TERT-BUTOXYVARBONYL) OXY]-N-{4-] [[(BENZYLOXY) CARBONYLAMINO]-3-FLUOROBENZYL} CARBAMATE] compound 53 (yield: [98%).] 1H-NMR [(CDC13)] 8 : 8.06 (bt, 1 H), 7.35-7. 45 (m, 5 H, Ph), 7.05-7. 12 (m, 2 H), 6.89 (bs, 1 H, NH), 5.22 (s, 2 H, [OCH2PH),] 4.68 (s, 2 H, CH2NO), 1.48 (s, 9 H, C [(CH3)] 3), 1.47 (s, 9 H, [ C (CH3) 3)]

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Digital Biotech Co., Ltd.; WO2004/35533; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)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 389890-43-1, HPLC of Formula: C9H17NO3

In a round-bottomed flask charged with tert-butyl(cis-3-hydroxycyclobutyl)carbamate (1.11 g, 5.93 mmol) and triethylamine (2.474 ml, 17.79 mmol) was added CH2Cl2 (12 ml). methanesulfonyl chloride (0.505 ml, 6.52 mmol) was added dropwise via syringe at -20 C. over 5 min. The reaction mixture was stirred at room temperature for 30 min, then diluted with water (15 mL) and extracted with CH2Cl2(2*). The organic extract was washed with saturated NH4Cl and dried over MgSO4. It was filtered and concentrated in vacuo to give cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (1.64 g, 6.1 mmol, 100% yield) as a off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics