Amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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 17193-28-1, HPLC of Formula: C6H12N2O

To a solution of 1-aminocyclopentane-l-carboxamide (1.00 g, 7.80 mmol) in DCM (16 niL) was added TEA (2.72 niL, 19.50 mmol). The mixture was cooled with an ice bath. Cyclopropanecarbonyl chloride (1.142 g, 10.92 mmol) in DCM (4 mL) was added dropwise to the stirred solution, and the reaction mixture was at RT for 18 hours. The reaction was diluted with 0 and DCM. The organic phase was collected. The aqueous phase was extracted (2X) with DCM. The combined organic phase was washed with brine, dried over sodium sulfate, and concentrated to give Intermediate 119a (0.889g, 4.53 mmol, 58.1 % yield) as a solid. RT =0.49 min, MS (ESI) m/z: 191 A (M+H)+. 1H NMR (400 MHz, CDCl3) delta 5.91 (br s, 2H), 5.76 – 5.57 (m, 1H), 2.49 – 2.25 (m, 1H), 2.07 (br d, J=16.7 Hz, 1H), 1.93 – 1.74 (m, 2H), 1.67 – 1.28 (m, 2H), 1.28 – 1.19 (m, 2H), 1.03 – 0.97 (m, 2H), 0.90 – 0.82 (m, 2H), 0.81 – 0.74 (m, 1H).

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; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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35623-11-1, name is 3-[(Methylamino)sulphonyl]benzoic Acid, 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. Application In Synthesis of 3-[(Methylamino)sulphonyl]benzoic Acid

A mixture of 3-methylsulfamoyl-benzoic acid (988 mg, 4.59 mmol) and SOCl2 (5 ml) was stirred at 70 C for 10 h. The mixture was concentrated under reduced pressure and azeotroped with toluene to give the crude carboxylic acid chloride. n-BuLi (5.83 ml, 15.2 mmol, 2.6 M in hexane) was added to a solution of 1,1,1,3,3,3- hexamethyldisilazane (3.2 ml, 15.2 mmol) in THF (15 ml) at -78 C. After stirring for 1 h at -78 C, ?- butyrolactone (395 mg, 4.59 mmol) in THF (5 ml) was added. After stirring for 15 min at -78 C, crude acid chloride in THF (15 ml) was added to the reaction mixture. The mixture was allowed to slowly warm to room temperature and stirring was continued for 1 h. The mixture was acidified with 5 M HCl aq. and extracted with diethyl ether twice. The combined organic extract was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (n-hexane/EtOAc) to afford the titled compound (1.43 g, quant.) as colorless oil.

The synthetic route of 35623-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kawada, Hatsuo; Ebiike, Hirosato; Tsukazaki, Masao; Nakamura, Mitsuaki; Morikami, Kenji; Yoshinari, Kiyoshi; Yoshida, Miyuki; Ogawa, Kotaro; Shimma, Nobuo; Tsukuda, Takuo; Ohwada, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 673 – 678;,
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Reference of 107017-73-2, 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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: tert-butyl l-((3-(diethoxyphosphoryl)propoxy)methyl)cyclopropylcarbamate [000471] To a solution of tert-butyl l-(hydroxymethyl)cyclopropylcarbamate (1 eq, from the previous step) in THF (0.1 M) at room temperature was added KOH (5 eq), tetrabutylammonium bromide (0.1 eq), and diethyl 3-bromopropylphosphonate (2 eq). The reaction was stirred at room temperature overnight. The mixture was concentrated en vaccuo and then taken up in DCM/water. The aqueous layer was extracted with DCM (2x). The combined organic layers were dried over anhydrous MgS04, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH system (ISCO) using a gradient of 0-100% ethyl acetate in hexanes and then 100% ethyl acetate to give the product as an oil.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; WU, Tom Yao-Hsiang; ZOU, Yefen; HOFFMAN, Timothy Z.; PAN, Jianfeng; WO2011/119759; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 912444-89-4,Some common heterocyclic compound, 912444-89-4, name is 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, molecular formula is C14H23NO4, 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 suspension of NaH (21.2 g, 0.318 mol, 60% dispersion in mineral oil) in DMSO (650 mL), S,S,S-trimethylsulfoxonium iodide (72.9 g, 0.331 mol) was added in small portions and stirred at rt for 1 h until gas evolution ceased. A solution of 1-tert-butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate (9) (34.3 g, 0.127 mol) in DMSO (150 mL) was added dropwise and the reaction mixture was stirred at 50 C overnight. The resulting solution was cooled to rt, poured into ice-cold H2O (1 L) and extracted with t-BuOMe (3×700 mL). The combined organic extracts were washed with brine (3×500 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The product was purified by column chromatography (gradient hexane to hexane – t-BuOMe (7:3) as eluent). Yield: 19.8 g (55 %); colourless oil. 1H NMR(500 MHz, CDCl3): delta 4.14 – 4.06 (m, 2H), 3.98 – 3.78 (m, 2H), 3.10 (s, 1H), 2.96 (s, 1H), 2.77 (dd, J=15.3, 6.4 Hz, 1H), 2.36 (dt, J=14.1, 6.5 Hz, 1H), 1.75 – 1.65 (m, 1H), 1.49 (dd, J=9.2, 4.3 Hz, 1H), 1.43 (s, 9H), 1.37 – 1.26 (m, 2H), 1.23 (t, J=7.1 Hz, 3H), 0.77 (t, J=6.6, 4.3 Hz, 1H). 13C NMR(126 MHz, CDCl3): delta 175.4, 155.1, 79.3, 60.6, 47.6, 47.2, 32.7, 32.4, 28.4, 27.7, 26.9, 24.7, 14.2. MS (APCI): m/z = 284 [M+H]+. Anal. Calcd. for C15H25NO4: C 63.58; H 8.89; N 4.94. Found: C 63.86; H 8.58; N 5.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, its application will become more common.

Reference:
Article; Yarmoliuk, Dmytro V.; Serhiichuk, Dmytro; Smyrnov, Vladyslav; Tymtsunik, Andriy V.; Hryshchuk, Oleksandr V.; Kuchkovska, Yuliya; Grygorenko, Oleksandr O.; Tetrahedron Letters; vol. 59; 52; (2018); p. 4611 – 4615;,
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121496-39-7, name is tert-Butyl benzyl(2-hydroxyethyl)carbamate, 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. Application In Synthesis of tert-Butyl benzyl(2-hydroxyethyl)carbamate

EXAMPLE IV N-tert.-Butoxycarbonyl-N-benzyl-glycine aldehyde STR32 Variant A 14.65 g (58.3 mmol) of the compound from Example III and 37.3 g (175 mmol) of pyridinium chlorochromate (Aldrich) are added to 500 ml of dichloromethane and the mixture is stirred at room temperature for 2 hours. The mixture is concentrated in a rotary evaporator and quickly filtered through a frit using 600 g of silica gel 60 (Merck) and a step gradient of 1 lof dichloromethane, 1l of dichloromethane/methanol 98/2 and 1.5 l of dichloromethane/methanol 95:5. 500 ml fractions were taken, and the product-containing eluates were combined, dried over sodium sulphate and concentrated in a rotary evaporator. Yield: 4 g (27.5% of theory)

The synthetic route of 121496-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5095006; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 830-43-3, A common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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 screw cap glass tube with a PP-cap was charged with a magnetic stirring bar, sulfonamide 1 or 6 (0.25 mmol, 1.0 equiv), glyoxylic acid monohydrate (2; 30.0 mg, 0.33 mmol, 1.3 equiv), phenylboronic acid (3a; 61.0 mg, 0.5 mmol, 2.0 equiv), and nitromethane (1.5 mL, 0.17 M wrt sulfonamide) and firmly closed. The resulting mixture was stirred at 60 C for 12 h. After cooling to r.t., the mixture was diluted with acetone and filtered through a short plug of Celite/silica gel. The plug was rinsed with additional acetone and the filtrate was concentrated under reduced pressure. Purification of the crude residue by flash column chromatography afforded the product.

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; Diehl, Andreas M.; Ouadoudi, Omar; Andreadou, Eleni; Manolikakes, Georg; Synthesis; vol. 50; 19; (2018); p. 3936 – 3946;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 50487-72-4,Some common heterocyclic compound, 50487-72-4, name is N,N-Diallyl-4-methylbenzenesulfonamide, molecular formula is C13H17NO2S, 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: The general procedure for metathesis reactions with ruthenium carbenes 10 was performed as follows: a certain amount of ruthenium carbene catalyst 10 (0.0005-0.0125mmol) and a solution of the substrate (0.5mmol) in 1.0mL dry CH2Cl2 (or toluene) was mixed in a reaction flask under nitrogen. The reaction mixture was stirred for 0.3-24h. At the end of the reaction (monitored by thin-layer chromatography (TLC)), the catalysts were separated by silica gel chromatography using CH2Cl2 as the eluent to remove trace amounts of Ru residues. Conversions were estimated by 1H NMR spectroscopy and obtained by comparing the ratios of the integrals of the starting materials with those of products. The catalytic activities of ruthenium carbene 10 for a variety of substrates are shown in Table 1.

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-Diallyl-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 26638-53-9, The chemical industry reduces the impact on the environment during synthesis 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, I believe this compound will play a more active role in future production and life.

6-Methyl-3- (methylthio) dibenzo [c, f] [1,2] thiazepin-11 ( 6H) -one 5,5-dioxide (3i) . To a solution of sodium thiomethoxide (116 mg, 1.65 mmol) in anhydrous DMF (2.0 mL) was added ketone 3d (462 mg, 1.50 mmol) and the resulting yellow suspension was stirred at room temperature for 1 h. Additional sodium thiomethoxide (26.3 mg, 0.375 mmol) was then added and stirring continued for a further 15 min. The reaction was then quenched with water (10 mL) and extracted with CH2CI2 (10 mL, 2 5 mL) . The combined organics were washed with water (20 mL) , dried over Na2SC>4, and concentrated to yield a yellow oil containing residual DMF. This crude was diluted with Et20 and chilled on ice causing the product to crystallize as pale-yellow needles. These crystals were washed with several small portions of ice-cold Et20 and dried to give the pure ketone 3i (331 mg, 69percent) . *H NMR (500 MHz, CDCI3) delta 8.31 (dd, J = 8.1, 1.6 Hz, 1H) , 7.92 (d, J = 8.3 Hz, 1H) , 7.73 (d, J = 2.0 Hz, 1H) , 7.62 (ddd, J = 8.0, 7.4, 1.7 Hz, 1H) , 7.48 (dd, J = 8.3, 2.0 Hz, 1H) , 7.40 – 7.33 (m, 2H) , 3.33 (s, 3H) , 2.59 (s, 3H) ; 13C NMR (126 MHz, CDC13) delta 189.5, 146.5, 141.4, 137.7, 134.7, 132.4, 132.2, 131.8, 131.7, 129.2, 126.4, 125.2, 121.4, 39.3, 15.0. LR-MS calcd. for C15H14NO3S2 [M+H]+ 320.04, found 320.75.

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, 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew; SAMES, Dalibor; JAVITCH, Jonathan A.; (187 pag.)WO2018/170275; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

154350-29-5, name is Cyclopropanesulfonamide, 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. Formula: C3H7NO2S

(15, 4R, 65, 145, 18R)-7-c-14-tert-Butoxycarbonylamino-18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3, 12,16-triazatricyclo[ 14.3.0.04’6]nonadec-7-ene- 4-carboxylic acid (490 mg, 0.79 mmol) was dissolved in 15 mL of THF and treated with CDI (179 mg, 1.10 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere.) After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (134 mg, 1.10 mmoL) and DBU (168 mg, 1.10 mmoL). After stirring overnight at rt, the THF was removed by rotary evaporation. The residue was dissolved in water and IN HCl was added until the pH = 5. This aqueous solution was extracted with EtOAc (3x). The combined EtOAc extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash column, eluting with 3percent methanol in methylene chloride, gave 300 mg (53percent) of (15, AR, 65, 145, 18R)- [1-cis-A-Cyclopropanesulfonylaminocarbonyl- 12-cyclopropyl- 18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3,12,16-triaza-tricyclo[14.3.0.04’6]nonadec-7-en- 14-yl]carbamic acid, tert-butyl ester as a white solid: LC-MS (Phenomenex 10 mum Cl 8 HPLC column: 3.0×50 mm length. Gradient: 100percent Solvent A/0percent Solvent B to 0percent Solvent A/100percent Solvent B. Gradient time: 2 min. Hold time: 1 min. Flow rate: 5 mL/min. Detector Wavelength: 220 nM. Solvent A: 10percent MeOH / 90percent H2O / 0.1percent TFA. Solvent B: 10percent H2O / 90percent MeOH / 0.1percent TFA.) (Retention time: 2.40 min), MS m/z 724 (M++l).

The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64057; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 7223-30-5, 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. 7223-30-5 name is 3-Phenylpropiolamide, 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.

General procedure: A degassed solution of 3-phenylpropiolamide (5.0 mmol) and N,N-dimethylethane-1,2-diamine (5.0mmol) in DMF (6.0 mL) was added through canula to a degassed solution of thevinyl iodide (1.0 mmol), Cs2CO3 (5.0 mmol) and CuI (2.0mmol) in DMF (25.0 mL) at 23 C. After stirring for the indicated time, thereaction was quenched with water and extracted with EtOAc (x3). The combined organic layers were washedwith brine, dried over Na2SO4 and filtered. The solventwas concentrated under reduced pressure, and the residue was purified byflash chromatography as indicated.

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

Reference:
Article; Garcia-Rodriguez, Jose; Mendiratta, Saurabh; White, Michael A.; Xie, Xiao-Song; De Brabander, Jef K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4393 – 4398;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics