Author: tianli

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, 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 37045-73-1, Computed Properties of C7H10N2O2S

General procedure: To a solution of N-[4-[5-(3-aminophenyl)-1,2,4-oxadiazol-3-yl]-3-chlorophenyl]-3-pyridinecarboxamide (VIc)(0.2 g, 0.51 mmol, 1 equiv) in THF (20 ml) was added phosgene(15wt % in toluene, 1.7 ml, 2.55 mmol, 5.0 equiv) and the reactionmixture was refluxed under N2 for 4 h. Upon the reactioncompletion as indicated by TLC the solution was concentratedunder reduced pressure, flushed with dry toluene. To theresulting residuewas added THF (20 ml), the appropriate aniline(0.77 mmol, 1.5 equiv) and DIPEA (0.132 g, 178 ml, 1.02 mmol, 2equiv) and the reaction mixture was refluxed under N2 overnight.Upon completion of the reaction as indicated by TLC, thesolution was concentrated, and the residue was purified bychromatography to give the desired final products (25-50).

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

Reference:
Article; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 7341-96-0, A common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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 4-(tert-butyl-dimethyl-silanyloxymethyl)-benzaldehyde oxime (which may be made as described in Preparation of Intermediate 17; 3 g, 11.3 mmol) in DMF (25 mL) was cooled to 0 C and N-chlorosuccinimide (1.51 g, 11.3 mmol) was added in portions. The cooling bath was removed and the reaction mixture was stirred for 2.5 h. The mixture was poured into ice- water (75 mL) and this was extracted with Et2O (3 x 100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to give a solid (3.5 g). The solid was dissolved in 50% aqueous tert-butanol (60 mL) in a flask that was open to the air. Propiolamide (which may be prepared as described in Matsumoto, T. et al. US 7,851,473 Column 128; 0.7 mL, 6.85 mmol) was added, followed by 1 M sodium ascorbate (1.13 mL, 1.13 mmol) and 0.1 M copper(II) sulfate (5.65 mL, 0.565 mmol). KHCO3 (4.52 g, 45.1 mmol) was added in portions and the reaction mixture was stirred at room temperature for 2.5 h. H2O (100 mL) was added and a yellow solid was filtered off and dried under high vacuum overnight (3 g). This material was taken up in CH2Cl2/acetone and filtered. The filtrate was evaporated and the residue was purified by chromatography (9-20% acetone/CH2Cl2) to give 3-[4-(tert-butyl-dimethyl- silanyloxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (800 mg, 21%). Purification of mixed fractions by chromatography (50-60% EtO Ac/toluene) provided a further 450 mg (12%) of 3-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ERICKSON, Shawn, David; GILLESPIE, Paul; MERTZ, Eric; WO2014/86704; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, 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. Formula: C10H17NO2

Solid NAHCO3 (0.0167 mol) and M-CPBA (0. 0128 mol) were added in portions to a stirred solution of cyclopent-3-enyl-carbamic acid tert-butyl ester IV-1 (0.0093 mol) in CH2C12 (60 mL). The mixture was stirred at 0 C for the first 2 h of the reaction and then allowed to stir for about 48 h at room temperature. Aqueous 20% NA2S03 (30 mL) was added, and the two layers were separated. The aqueous layer was extracted with CH2C12 (20 mL X 3), and the combined organic layers were washed with 20% NA2SO3 (30 mL X 1), 5 % NAHCO3 (30 mL X 1), and water (30 mL X 1). The combined organic phase was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 100% dichloromethane) to give pure product as a colorless oil (64%).

The synthetic route of tert-Butyl cyclopent-3-en-1-ylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2005/26111; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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.

Example 126 Preparation of 5,7-Dimethoxy-2-(3-methoxyphenyl)quinazolin-4(3H)-one A mixture of 2-amino-4,6-dimethoxybenzamide (0.0600 g, 0.306 mmol), 3-methoxybenzaldehyde (0.306 mmol), NaHSO3 (94%, 0.0474 g, 0.428 mmol), and p-TsOH.H2O (0.0175 g, 0.0918 mmol) in DMA (3.06 mL) was heated at 140 C. for 20 hours. The mixture was diluted with EtOAc (300 mL), washed with water (3*75 mL), then brine (75 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified on silica gel (40 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (69%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): delta 12.04 (s, 1H), 7.82-7.70 (m, 2H), 7.43 (t, J=7.98 Hz, 1H), 7.13 (dd, J=8.19, 2.46 Hz, 1H), 6.76 (d, J=2.19 Hz, 1H), 6.55 (d, J=2.19 Hz, 1H), 3.92-3.82 (m, 9H); MS (APCI) m/z 313 [C17H16N2O4+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature 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.

General procedure: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and iBET726(36 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mircoL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table III shown below.

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; UNIVERSITY OF DUNDEE; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; CIULLI, Alessio; (279 pag.)WO2019/238886; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 116195-15-4,Some common heterocyclic compound, 116195-15-4, name is (R)-(-)-(2-Methylacryloyl)-2,10-camphorsultam, molecular formula is C14H21NO3S, 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 2. Synthesis of (3aS,6R,7aR)-8,8-dimethyl-1-{[(5R)-5-methyl-4,5-dihydro-1 H-pyrazol-5- yl]carbonyl}hexahydro-3a,6-methano-2, 1 -benzisothiazole 2,2-dioxideTMSCHN262% Procedure: To a solution of (trimethylsilyl)diazomethane in ether (2M; 20ml) was added the solid (3aS,6R,7aR)-1 -methacryloyl-delta.delta-dimethylhexahydro-Sa.beta-methano^.i -benzisothiazole 2,2-dioxide and then the reaction mixture was stirred at room temperature for 72 hours. A solution formed. The solution was evaporated in vacuo and then diluted with methylene chloride (50ml), cooled to 0 C and then trifluoroacetic acid (1.2ml) was added drop wise. The mixture was stirred for 2h at 00C. The reaction mixture was diluted with ethyl acetate (200ml) and washed with sat. NaHCO3 (200 imL). The organic phase was washed with brine (200 mL) and then dried with magnesium sulfate. The organic solvents were removed in vacuo and the product purified by silica gel chromatography (eluant 10-100 EtOAc in hexane) and then treated with ether. The product was isolated as a solid (2.9Og, 56% yield). Optical rotation = 0.02Og in 2ml; c=0.01g/ml {C= 1 (CHCI3)); measurement -0.287; optical rotation = – 0.287×4000/10 = – 114.8 (using a Perkin-Elmer 241 Polarimeter).Combustion Analysis:1 H NMR (400 MHz, DMSO-D6) delta ppm 0.87 (m, 3 H), 0.98 (s, 3 H),1.21 (m, 1 H), 1.32 (s, 3 H), 1.40 (m, 1 H), 1.71 (m, 4 H), 1.85 (dd, J=13.35, 7.70 Hz, 1 H), 2.54 (dd, J=17.16, 1.56 Hz, 1 H), 3.13 (dt, J=17.20, 1.34 Hz, 1 H)1 3.64 (d, J=14.04 Hz, 1 H), 3.74 (d, J=14.04 Hz1 1 H), 3.83 (dd, J=7.60, 4.68 Hz, 1 H), 6.62 ;(t, J=1.46 Hz, 1 H), 6.78 (S1 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-(-)-(2-Methylacryloyl)-2,10-camphorsultam, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65503; (2008); 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. 683-57-8, name is 2-Bromoacetamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromoacetamide

Example 304J 2-({3-[1-(cyclobutylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide The product of Example 3041 (0.048 g, 0.11 mmol) in N,N-dimethylformamide (2 ML) was reacted with cesium carbonate (0.15 g, 0.45 mmol), bromoacetamide (0.026 ML, 0.18 mmol), and a catalytic amount of tetrabutylammonium iodide at 25 C. for 3 hours.The reaction was concentrated under a stream of nitrogen stream of nitrogen warmed through a manifold heated to 165 C. and the resulting residue was triturated with water, filtered and dried.The resulting solid was triturated in hot ethyl acetate, filtered, and dried to give the title compound (0.020 g, 37%). MS (ESI-) m/z 482 (M-H)-. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 2H) 1.99 (m, 4H) 3.60 (m, 1H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (t, J=7.17 Hz, 1H) 7.20 (m, 3H) 7.40 (s, 1H) 7.50 (m, 1H) 7.65 (m, 2H) 8.05 (d, J=7.72 Hz, 1H) 16.25 (s, 1H).The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 1H) 1.99 (m, 4H) 3.61 (m, 2H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (m, 1H) 7.21 (m, 2H) 7.40 (s, 2H) 7.50 (m, 1H) 7.64 (m, 2H) 8.06 (dd, J=7.91, 1.29 Hz, 1H) 8.32 (s, 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 683-57-8.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pamela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/167123; (2004); A1;,
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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromomethylbenzenesulfonamide

To a stirring solution of 4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3- dihydro-lH-inden-l-one (80 mg, 0.25 mmol) in acetonitrile (10 ml_), was added potassium carbonate (104 mg, 0.75 mmol) and 4-bromomethyl-benzenesulfonamide (125 mg, 0.5 mmol) and the resultant reaction mixture was heated to 80 ¡ãC for 16 h. The reaction mixture was cooled to RT and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by columnchromatography (silica gel, 0-70percent ethyl acetate in pet ether) to afford title compound as a solid (40 mg, 33percent).UPLC-MS (M + l) : 490.11 ; UPLC-MS RT (min) : 2.4

The synthetic route of 40724-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H¡ãjland; WO2011/134468; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 563-83-7, name is Isobutyramide, 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. Recommanded Product: Isobutyramide

General procedure: To a mixture of amide (2 mmol) and amine (2.6 mmol) ina 10 mL round bottomed ask was added [PyPS]3PW12O40 (140 mg, 0.04 mmol). The reaction mixture was stirred at the corresponding temperature under MW (700 W). The progress of the reaction was monitored by TLC. On completion, the mixture was diluted with ethyl acetate (20 mL) with stirring for 30 min. The insoluble catalyst was recovered by filtration or centrifugation. The filtrate was evaporated and the residue in almost pure form. Recrystallization or column chromatography could be used for further purication.

The synthetic route of Isobutyramide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Renzhong; Yang, Yang; Chen, Zhikai; Lai, Wenchen; Ma, Yongfeng; Wang, Quan; Yuan, Rongxin; Tetrahedron; vol. 70; 50; (2014); p. 9492 – 9499;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 35303-76-5, 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. 35303-76-5 name is 4-(2-Aminoethyl)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.

A solution of 3- (4-fluorophenyl) propan-l-amine hydrochloride(2.11 mmol) in THF (10 ml)Was added DIPEA (6.32 mmol) and triphosgene (0.843 mmol)And the reaction mixture was stirred at 0 ¡ã C for 30 minutes.Then, 4- (2-aminoethyl) benzenesulfonamide (2.11 mmol) was added thereto,The reaction mixture was warmed to room temperature and stirred for 16 hours.To the reaction mixture was added 10percent [v / v] sodium hydrogencarbonate solution (20 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was collected and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude extract thus obtained was purified by silica gel flash column chromatography (eluting with hexane solution containing 50 to 80percent [v / v] ethyl acetate) to give 4- – (3- (3- (4-fluorophenyl) propyl) ureido) ethyl) benzenesulfonamide was obtained

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

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics