Category: amides-buliding-blocks

22958-64-1, 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. 22958-64-1, name is 2-(4-Sulfamoylphenyl)acetic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00382] 1H NMR (400 MHz, DMSO-cfe) d 7.80 – 7.74 (m, 2H), 7.48 (d, J= 8.4 Hz, 2H), 7.41 – 7.29 (m, 3H), 7.22 – 7.15 (m, 2H), 7.07 (td, J= 8.3, 1.8 Hz, 1H), 3.95 (s, 2H), 3.75 (s, 2H), 2.81 – 2.64 (m, 8H); LC-MS Rt 0.53 min, MS m/z [M+H]+ 499.4

The synthetic route of 2-(4-Sulfamoylphenyl)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 72179-84-1 name is (Methylsulfamoyl)amine, 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. 72179-84-1

Example 67 (100 mg, 0.259 mmol) was dissolved in tetrahydrofuran (4 mL) and carbonyldiimidazole (63.1 mg, 0.389 mmol) was added. The mixture was heated to 60 C for 1 hour. More carbonyldiimidazole (63.1 mg, 0.3 89 mmol) was added, and the resultant solution was stirred at 60 C for 1 hour. The solution was cooled down to room temperature and was then added dropwise through a syringe to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.117 mL 0.778 mmol, DBU) and N-methylsulfuric diamide (86 mg, 0.778 mmol) in 0.6 mL tetrahydrofuran. The resulting mixture was stirred at room temperature overnight. The mixture was acidified with 1 N HC1 to pH=6-7 and then extracted with ethyl acetate 3 times. The organic layers were combined and concentrated. The residue was diluted with methanol to give a solution which was purified by preparative HPLC (0.1% CF3CO2H in H20/CH3CN) and lyophilized to give the titled compound (72.5 mg, 0.152 mmol, 58.5% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.39 (s, 1H), 7.46 (q, J = 4.9, 4.5 Hz, 1H), 7.14 (dd, J = 56.8, 38.2 Hz, 5H), 6.50 (s, 2H), 3.74 (s, 6H), 3.67-3.58 (m, 1H), 3.46 (d, J = 19.0 Hz, 4H), 3.19 (s,1H), 2.60 (s, 3H), 2.40 (s, 2H), 1.98 (s, 3H), 1.82 (a, J = 16.8 Hz, 2H); LC-MS (ESI+) m/z 478.2 (M+H), RT = 1.9 19 minutes.

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

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below.

A suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (182 mg, 0.918 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (819 mg, 3.67 mmol) and K2C03(S) (634 mg, 4.59 mmol) in DMSO (918 was heated to 90 ¡ãC, then treated with water (5 mL). The resulting mixture was stirred for 1 hour at 90 ¡ãC, then cooled to ambient temperature and filtered to cleanly provide the title compound (1.0 g, 41percent yield). MS (apci) m/z = 320.1 (M+H).

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; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

72791-76-5, The chemical industry reduces the impact on the environment during synthesis 72791-76-5, name is Benzyl bis(2-chloroethyl)carbamate, I believe this compound will play a more active role in future production and life.

2-phenylacetonitrile (5.000 g, 42.680 mmol) and sodium hydride (60.00%, 3.755 g, 93.897 mmol) was dissolved in N,N-dimethylformamide (100 mL) at 0 C and stirred for 30 minutes then benzyl bis(2-chloroethyl)carbamate (11.787 g, 42.680 mmol) was added thereto after further stirring at 60 C for 3 hours, the reaction was terminated by lowering the temperature to room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 30% to 100%) and concentrated to give the title compound (7.500 g, 54.8%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis Benzyl bis(2-chloroethyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 64214-66-0, name is 4-Chloro-N-methoxy-N-methylbutanamide, molecular formula is C6H12ClNO2, 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. 64214-66-0

Step B 3-chloropropyl 3,5-dimethylphenyl ketone A solution of 10.2 mL (13.9 g; 72 mmol) 5-bromo-m-xylene in 200 mL of anhydrous tetrahydrofuran was stirred under nitrogen at -78 C. as 35.8 mL (84 mmol) of 2.5M n-butyllithium in tetrahydrofuran was added dropwise. After 15 minutes at -78 C., a solution of 10.0 g (60 mmol) of 4-chloro-N-methoxy-N-methylbutyramide (from Step A) in 30 mL of anhydrous tetrahydrofuran was added dropwise over 25-30 minutes. The resulting solution was maintained at -78 C. for 45 minutes and then warmed briefly to room temperature. The reaction was quenched by addition of 40 ml of 2N hydrochloric acid and then partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and then saturated aqueous sodium chloride solution. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue afforded 8.91 g (70%) of an oil, which had satisfactory purity by 1 H NMR (CDCl3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64214-66-0, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5756507; (1998); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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 94838-59-2. 94838-59-2

A mixture of 2-Deoxy-D-ribose (Apollo, 2g, 14.8 mmol), tert-butyl 4- aminophenetylcarbamate (Ark Pharm, 5.14 g, 20.7 mmol) and montmorillonite (12 g) was stirred at RT in MeCN (100 mL) for three days. The reaction mixture was then filtered through a celite pad which was subsequently washed with EtOAc. The filtrate was concentrated under reduced pressure. Purification of this crude (5.2 g) by flash chromatography on silica (Cyclohexane: EtOAc, gradient from 7:3 to 6:4) afforded the title compounds: First eluting fraction (Intermediate 1): [2-((lS,9S,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (1.88 g, 37%), yellow solid, Rf=0.35 (Cyclohexane:EtOAc, 2:8), lH NMR (CDC13) : 6.98 (dd, IH, J=8.1 Hz, J=1.5 Hz), 6.94 (dd, IH, J=1.5 Hz), 6.59 (d, IH, J=8.1 Hz), 4.67-4.36 (m, IH), 4.60-4.50 (m, IH), 4.45-4.35 (m, IH), 3.81-3.65 (m, 2H), 3.63 (brs, IH), 3.37-3.20 (m, 2H), 2.91 (t, IH, J=10.0 Hz), 2.71-2.61 (m, 2H), 2.15-2.05 (m, 2H), 2.15-2.05 (m, 2H), 1.88 (dd, IH, J=4.7 Hz, J=2.0 Hz), 1.43 (s, 9H). Second eluting fraction (intyermediate 2): [2-((lR,9R,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (2.0 g, 41%), white solid, Rf=0.25 (Cyclohexane:EtOAc, 2:8), lH NMR (CDCI3) : 7.01-6.93 (m, 2H), 6.51 (d, IH, J=8.0 Hz), 4.71-4.68 (m, IH), 4.60-4.48 (m,lH), 3.67-3.61 (m, IH), 3.59-3.48 (m, 3H), 3.38- 3.24 (m, 2H), 2.67 (t, 2H, J=7.0 Hz), 2.56 (dt, IH, J=13.5 Hz, J=3.0 Hz, J=3.0 Hz), 2.31 (d, IH, 7.3 Hz), 1.59-1.53 (m,lH), 1.43 (s, 9H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of tert-Butyl 4-aminophenethylcarbamate.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; JOHNSON, Theresa L.; GRAEDLER, Ulrich; JIANG, Xuliang; ROCHE, Didier; LEMOINE, Hugues; GILARDONE, Marine; (61 pag.)WO2017/173049; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112253-70-0, name is 2-Amino-4-bromobenzamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 112253-70-0

To bis(triphenylphosphine)palladium(II) dichloride (98 mg, 0.14 mmol), 2-amino-4-bromobenzamide (600 mg, 2.79 mmol), and l-methyl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (754 mg, 3.62 mmol) were added acetonitrile (9 mL) and 1M aq Na2CC>3 (9 mL, 9 mmol). The reaction vessel was evacuated and flushed with argon (3X). The mixture was heated in a microwave reactor at 160 C for 20 min. The mixture was allowed to cool to rt, the organic layer was decanted, and the aqueous layer was retained. The organic layer was concentrated under reduced pressure and the residue was diluted with water. The resulting solid was collected by filtration washing with water and acetonitrile. The retained aqueous layer from above was filtered, and the collected solid was washed with water and acetonitrile. The collected solids were combined to afford 2-amino-4-(l -methyl- 1H- pyrazol-4-yl)benzamide (520 mg, 86%). LCMS (ESI) m/z 217 (M + H)+.

Statistics shows that 112253-70-0 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-bromobenzamide.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30912; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

815-06-5, 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. 815-06-5, name is N-Methyl-2,2,2-trifluoroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 31a. Sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added under nitrogen atmosphere to a solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL) at 0 C. The reaction mixture was stirred for 90 min at 0 C., and then 6-bromo-1-hexene (100 g, 1 eq.) was added dropwise over 45 min. The reaction mixture was allowed to warm up to room temperature, and stirred for 3 days at room temperature. The reaction mixture was then poured into water and extracted tree time with EtOAc. The combined organics layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to produce compound 31a as colorless oil in 56% yield. 1H NMR (DMSO-d6, 400 MHz) delta 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2.00-2.06 (m, 2H), 2.93-3.07 (2m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, 1H).

The synthetic route of 815-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2009/202480; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1, 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. 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Asymmetric synthesis of (-)-2-(diphenylmethyl)sulphinylacetamideGeneral procedure for examples 1 to 10 : Diphenylmethylthioacetamide (7.70 g ; 0.03 mol ; 1.0 eq) was dissolved in the solvent (toluene ; 77 mL ; 10 vol.) under argon. To the solution were added (S,S)-(-)-diethyl-tartrate (1.23 g ; 0.006 mol; 0.2 eq) and titanium (IV) tetraisopropoxide (0.85 g ; 0.88 mL ; 0.003 mol; 0.1 eq) and water (27 muL minus the sum of water present in reactants and solvent already introduced ; 0.0015 mol ; 0.05 eq) at 55C. In these conditions, the resulting chiral titanium complex has the stoichiometry (DET/Ti(OiPr)4/H2O : 2/1/0.5) and represents 0.1 eq of diphenylmethylthioacetamide. Stirring was maintained at 55C during 50 minutes. After cooling to room temperature (25C), were added to the mixture diisopropylethylamine (0.39 g ; 0.52 mL ; 0.003 mol ; 0.1 eq) and cumene hydroperoxide (4.55 g ; 5.0 mL ; 0.03 mol ; 1.0 eq). After contacting during about an hour, the formed precipitate is isolated by filtration. All the following experiments were performed in accordance with the conditions of the general procedure, by modifying parameters as indicated in tables 1-10.; Example 2 : Influence of the amount of water on the enantioselectivity of asymmetric oxidation In this experiment, the ratio of water was varied with respect to the titanium tetraisopropoxide from 0 to 1 equivalent, all the other parameters being as defined in the above general procedure. Notably, the ratio of the titanium chiral complex was maintained at 0.1 equivalent with respect to the diphenylmethylthioacetamide. [Table 2] EntryAmount of water (equivalent)E. e. (%)Purity (%)Yield (%)1080-90.320.493> 999230.894> 9988419199.590 – = Not determined These results show that the amount of water has an effect on the enantioselectivity of the reaction. Thus, the best enantioselectivities are achieved when an amount of water comprised between 0.4 and 0.8 equivalents are used. On the opposite, the enantioselectivity drops notably in the absence of water.

The synthetic route of 2-[(Diphenylmethyl)thio]acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON FRANCE; EP1516869; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, 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 27366-72-9. 27366-72-9

EXAMPLE 1 Preparation of Ethyl 2-Dimethylaminomethyl-4-thiazolecarboxylate A reaction mixture was prepared containing 15.5 g. of dimethylaminothioacetamide hydrochloride, 20.5 g. of ethyl bromopyruvate and 100 ml. of ethanol. The reaction mixture was heated to refluxing temperature for about four hours after which time the solvent was removed in vacuo in a rotary evaporator. The residue, containing ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate hydrochloride formed in the above reaction, was dissolved in a mixture of ether and water. The aqueous layer was separated. The ether layer was extracted with an equal volume of water and then discarded. The two aqueous layers were combined and washed with ether. The ether layer was again discarded and the aqueous layer cooled to a temperature in the range of 0-5 C. Solid potassium carbonate was added until the aqueous layer gave a basic reaction to litmus. An oil separated comprising ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate free base. The oily layer was extracted with ether and the ether extract separated and dried. The ether was removed by evaporation in vacuo. The resulting residue was purified by gradient high pressure liquid chromatography (silica, ethyl acetate). Ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate thus obtained had the following physical characteristics: Analysis Calculated: C, 50.45; H, 6.59; N, 13.07; S, 14.96 Found: C, 50.13; H, 6.39; N, 12.89; S, 15.04. The nmr spectrum in CDCl3 (TMS internal standard) gave the following signals (delta): 1.43 (triplet, 3H), 2.40 (singlet, 6H), 3.87 (singlet, 2H), 4.47 (quartet, 2H), 8.20 (singlet, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-(Dimethylamino)ethanethioamide hydrochloride.

Reference:
Patent; Eli Lilly and Company; US4474794; (1984); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics