Category: amides-buliding-blocks

Electric Literature of 78191-00-1,Some common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, molecular formula is C4H9NO2, 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 n-BuLi (2M in pentane ; 15.24 mL, 0.0305 mol) in 70 mL of dry ether at-78C was added dropwise 29 (6.3 g, 0.0277 mol) in 30 mL of ether over a period of 30 minutes. The mixture was stirred for lh, then N-methoxy-N-methylacetamide (3.83 mL, 0.036 mol) was added dropwise over 10 minutes. After lh of stirring at-78C the reaction mixture was washed with sat’d NAHCO3 and extracted with ether. The organic layer was dried with NA2S04 and concentrated in vacuo to give 6.66 g (89%) of 16 as an oil that was used directly for the next step.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/87699; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, 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. Quality Control of tert-Butyl methylsulfonylcarbamate

To a solution of benzyl 4-(hydroxymethyl)-3,3-dimethyl-pyrrolidine-1-carboxylate (300 mg, 1.14 mmol), tert-butyl N-methylsulfonylcarbamate (330 mg, 1.7 mmol) and PPh3 (890 mg, 3.4 mmol) in THF (20 mL) was added DEAD (390 muL, 2.5 mmol) dropwise and the reaction mixture stirred at ambient temperature under N2 for 16 hours. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (silica, 0 to 50% EtOAc/PE gradient elution) to give benzyl 4-[[tert- butoxycarbonyl(methylsulfonyl)amino]methyl]-3,3-dimethyl-pyrrolidine-1-carboxylate as a colourless oil that was taken directly on to the next step; MS m/z: 441 (M+H)+.

The synthetic route of tert-Butyl methylsulfonylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); 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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide, A new synthetic method of this compound is introduced below., SDS of cas: 22227-26-5

Charged 3,5-bis(trifluoromethyl)benzonitrile (100 gm, 1 meq.), 2 (N) Sodium hydroxide (21.7 gm, 1.3 meq.) into 400 ml methanol and stirred the reaction mass at 20 – 30¡ãC for 2-3 hrs. Added Dimethyl sulphoxide (100 ml) followed by dilute 30percent H202 solution (100 gm diluted in 300m1 water, 2.1 eq.) at 20 -35¡ãC. Stirred the mass for 2-3 hrs. at 20-30¡ãC and confirmed reaction completion by HPLC. Reaction mass quenched by addition of water (500 ml, S Vol). Filtered the slurry and washed the wet cake by water (500 ml, SVol). Dried under vacuum at 50-60¡ãC to get 100 gm 3, 5-bis (trifluoromethyl) benzamide (Purity 99 percent). Charged 3, 5-bis (trifluoromethyl) benzamide, prepared according to procedures a or b, as described above, (100 gm, 1 meq) into N, N Dimethyl formamide (100 ml, 1 vol). Added N, N Dimethyl formamide dimethyl acetal (70 gm, 1.5 meq) at 20-30¡ãC and stirred the reaction mass for 2-3 hrs. Reaction completion for the formation N-((dimethylamino)methylene)-3,5- bis(trifluoromethyl)benzamide was confirmed by HPLC. Cooled reaction mass to 10-15¡ãC and added acetic acid (S00 ml, S vol.) followed by hydrazine hydrate (31 gm, 1.5 meq). Reaction mass was heated to S0-SS¡ãC and stirred for 2-3 hrs. at same temparature. Reaction was monitored by HPLC. Cooled reaction mass to 20-30¡ãC and quenched by addition of water (2.S L, 2S vol.). Filtered the slurry and washed the wet cake by water (S00 ml, S vol.). Dried under vacuum at 50-60¡ãC to get 3 -(3,5 -bis(trifluoromethyl)phenyl)- 1 H-i ,2,4-triazole (94 gr, Purity 97percent).

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; WATSON LABORATORIES INC.; MUTHUSAMY, Anantha Rajmohan; KANNIAH, Sundara Lakshmi; RAVI, Akash; DAS, Tonmoy Chitta; CHEMATE, Rajendra Popat; SINGH, Anil Kumar; WAGH, Yogesh Dhananjay; (60 pag.)WO2018/129227; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 406233-31-6, name is 4-Fluoro-3-nitrobenzenesulfonamide, 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 406233-31-6, Quality Control of 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-nitrobenzenesulfonamide, and friends who are interested can also refer to it.

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

Electric Literature of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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 stirred solution of the intermediates compound2a-2d (1 mmol) with triethylamine (2 mmol) into DMF(12 mL), then a mixture of 1-ethyl-(3-(3-dimethylamino)-propyl)-carbodiimide hydrochloride (EDCI) (1 mmol) andN-hydroxybenzotriazole (HOBt) (1 mmol) was placed in thereaction system, stirred at room temperature for 30 min, themixture of substituted benzene sulfonamide (1 mmol) andDMF (5 mL) was added in the reaction system, the reactionmixture was monitored by TLC. After completion of the reaction,the product was extracted from chloroform with water,0.2 mol/L hydrochloric acid, water, 2.0 mol/L sodium hydroxide,saturated sodium chloride successively, and then dried,concentrated, and purified by preparative thin layer chromatographyfollowed by recrystallization from ethanol.

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

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Liu, Hao; Li, Hai-Dong; Li, Qing-Shan; Wang, Li; Zhang, Li-Song; Yao, Xiao-Kang; Cao, Hai-Qun; Chemical and Pharmaceutical Bulletin; vol. 66; 4; (2018); p. 358 – 362;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 77925-80-5, A common heterocyclic compound, 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, molecular formula is C13H12N2O5S, 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.

2S,5S)-1-(tert-butyl) 2-ethyl 5-hydroxylpiperidine-1,2-dicarboxylate (130 g, 475.62 mmol), triphenylphosphine (212 g, 809.16 mmol) and N-(benzyloxy)-2-nitrophenyl-1-sulfamide (161.4 g, 523.5 mmol) were dissolved in tetrahydrofuran (1500 mL), cooled to 0C, diethyl azodicarboxylate (149.1 g, 856.16 mmol) was added dropwise under nitrogen gas protection, after adding, the reaction solution was heated to room temperature and stirred overnight, concentrated, and the crude product was purified by silica gel chromatograph (ethyl acetate : petroleum ether = 1:5) to obtain the title compound as a yellow oil (210 g, yield 78%).

The synthetic route of 77925-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (77 pag.)EP3281942; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7150-72-3, name is tert-Butyl vinylcarbamate, 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 7150-72-3, Recommanded Product: 7150-72-3

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (786 mg, 2.5 mmol), N-vinyl-carbamic acid tert-butyl ester (1.432 g, 10 mmol) and benzyltriethylammonium chloride (57 mg, 0.25 mmol) were covered with dioxane (11 ml) under argon. Rh2(OAc)4 (11 mg, 0.025 mmol) was added and the suspension stirred at room temperature for 15 minutes. The slurry became thick and difficult to stir so a further 4 ml of dioxane was added. The mixture was stirred at 75 C. for 2 hours, then shaken between tBuOMe and water. The organic phase was washed with water and NaCl (satd), dried over MgSO4 and evaporated to yield a brown viscous oil (1.353 g), which was chromatographed on silica to yield 2-(4-fluoro-phenyl)-cyclopropyl-carbamic acid tert-butyl ester 369 mg (59%, m.p. 117-118 C.) cis and 125 mg (20% m.p. 102-105 C.) trans. 1H-NMR (CDCl3, signals for the cis isomer) 0.93 (1H, m), 1.32 (9H, s), 2.20 (1H, m), 2.89 (1H, m), 4.23 (1H, m), 6.98 (2H, t), 7.18 (2H, t).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; O’Sullivan, Anthony Cornelius; Loiseleur, Olivier; Stierli, Daniel; Luksch, Torsten; Pitterna, Thomas; US2014/378461; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, molecular formula is C6H13NO4S, 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: tert-Butyl methylsulfonylcarbamate

Example 243: t-ButylN-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methyl-1-butanol (97.2 mg, 0.259 mmol) obtained in Example 239, t-butyl N-methylsulfonylcarbamate (101 mg, 0.518 mmol) and triphenylphosphine (138 mg, 0.518 mmol) were dissolved in tetrahydrofuran (3 ml), followed by the addition of diisoopropyl azodicarboxylate (102 mul, 0.518 mmol) at room temperature.. The reaction mixture was stirred at room temperature for 18 hours.. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then concenetrated.. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:2 elude was concentrated, whereby the title compound (136 mg, 0.246 mmol, 95%) was obtained as a colorless amorphous substance.1H-NMR (400 MHz, CDCl3) delta: 1.33(3H,d,J=6.8Hz), 1.35-1.45(1H,m), 1.52(9H,s), 1.99-2.08(1H,m), 2.70-2.78(1H,m), 3.27(3H,s), 3.65-3.76(2H,m), 4.45(1H,d,J=7.6Hz), 6.77(1H,td,J=9.0,4.6Hz), 6.91-6.97(1H,m), 7.32(2H,d,J=8.5Hz), 7.38-7.45(1H,m), 7.50(2H,d,J=8.5Hz). MS m/z: 552 (M++H), 574 (M++Na). FAB-MS: 552.1070 (Calcd for C23H29ClF2NO6S2: 552.1093), 574.0875 (Calcd for C23H28ClF2NO6S2Na: 574.0912).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147751-16-4, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 32428-71-0, name is 2-Chloro-N-(2-ethyl-6-methylphenyl)acetamide, 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 32428-71-0, Formula: C11H14ClNO

A. 1-[(2-Ethyl-6-methylphenyl)carbamoylmethyl]-2-methyl-2-imidazoline. In a manner similar to Ex. IA react 21.17 gm. (0.1 M) of 2-chloro-2′-ethyl-6′-methylacetanilide and 42.1 gm. (0.5 M) of lysidine in 250 ml. of nitromethane, to obtain the title compound: NMR (CDCl3): delta=1.16(t,3), 1.97(s,3), 2.18(s,3), 2.54 (q,2), 3.10-3.70(m,4), 3.87(s,2), 7.15 (s,3) and 8.78(bs,1)ppm.

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; Berlex Laboratories, Inc.; US4353921; (1982); A;,
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 402-46-0 as follows. name: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 ¡Á 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics