Category: amides-buliding-blocks

Synthetic Route of 79722-21-7, 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. 79722-21-7, name is tert-Butyl benzyloxycarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

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, tert-Butyl benzyloxycarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
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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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound 2 (15 g, 57.47 mmol),trans-4-BOC-aminocyclohexanol (24.7g, 114.9mmol),Triphenylphosphine (30.1 g, 114.9 mmol) and 150 ml of THF were cooled to 0 C in an ice-salt bath.Add DIAD (23.2g, 114.9mmol) dropwise,Warm to room temperature and stir overnight.Column chromatography gave 13.1 g of solid, yield: 49.7%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Zheng Nan; Hao Qun; Zhou Weicheng; Lin Kuaile; Pan Jing; Chen Liang; Zhou Ting; Liu Zhenren; (39 pag.)CN110655519; (2020); A;,
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Some common heterocyclic compound, 5900-59-4, name is 2-Amino-4-chlorobenzamide, molecular formula is C7H7ClN2O, 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. Safety of 2-Amino-4-chlorobenzamide

EXAMPLE 1 To a mixture of 7.73 g of 2-chloro-N-(3,4-dimetoxyphenethyl)acetamide, 5.12 g of 2-amino-4-chlorobenzamide, 13.5 g of sodium iodide and 3.63 g of magnesium oxide was added 30 ml of dimethylformamide and the resulting mixture was stirred at 90¡ã to 100¡ã C. for 4.5 hours. The reaction solution was concentrated under reduced pressure and the residue was extracted with 500 ml of chloroform. The chloroform extract was washed successively with 10percent hydrochloric acid, water, a 5percent aqueous sodium carbonate solution, a 5percent aqueous sodium sulfite solution and water, dried and then concentrated to dryness under reduced pressure. The residue was recrystallized from methanol to obtain 8.01 g of 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide having a melting point of 167.5¡ã-168.5¡ã C. Elemental Analysis for C19 H22 O4 N3 Cl: Calcd. (percent): C, 58.24; H, 5.66; N, 10.72. Found (percent): C, 58.26; H, 5.59; N, 10.70.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5900-59-4, its application will become more common.

Reference:
Patent; Daiichi Seiyaku Co., Ltd.; US4297357; (1981); A;,
Amide – Wikipedia,
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Electric Literature of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to the described general procedure (GP11), N-alkylation of commercially available 4(5)-methylimidazole (4.343 g ; 52.90 mmol) with (2-bromo-ethyl)-carbamic acid benzyl ester (15.019 g ; 58.19 mmol), and subsequent purification by FC (DCM /MeOH =10/1) afforded a mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester, and [2-(5-methyl-imidazol-1-yl)ethyl]-carbamic acid benzyl ester (ratio of regioisomers close to 1/1, according to 1H-NMR) as a yellow oil (4.270 g ; 31%). LC-MS: tR=0.68 min. (2 regioisomers); [M+H]+: 260.46 g/mol. A mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]carbamic acid benzyl ester, [2-(5-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester (1.198 g; 4.62 mmol; ratio of regioisomers close to 1/1, according to 1H-NMR), and 10% palladium on activated charcoal (240 mg; 20% in mass) was placed under nitrogen before addition of anh. MeOH (20 ml). The resulting mixture was placed under vacuum, and then under hydrogen (1 atm), and stirring at rt was continued for 2.5 h. Filtration over a pad of celite, concentration to dryness under reduced pressure afforded a mixture of 2-(4-methyl-imidazol-1-yl)-ethylamine, and 2-(5-methyl-imidazol-1-yl)-ethylamine as a slightly yellow oil (540 mg; 93%). LC-MS: tR=0.17 min. (2 regioisomers); [M+H]+: no ionisation. These primary amines were converted to the corresponding chlorhydrate salt by treatment of a solution of regioisomeric amines (540 mg ; 4.31 mmol) in dichloromethane (5 ml) with 4N HCl in 1,4-dioxane (3.25 ml ; 3 eq.). Concentration to dryness under reduced pressure afforded a beige solid which was further dried under HV.

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (2011); A1;,
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Electric Literature of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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 mixture of l-methylpiperidine-4-carboxylic acid (500 mg, 3.49 mmol), HATU (1.59 g, 4T8mmol) and DIPEA (1.13 g, 8.73 mmol) in DCM (20 mL) was stirred at room temperature for 0.5 h. Then / -butyl 4-aminophenethylcarbamate (825 mg, 3.49 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as white solid (170 mg, 13.5 % yield). ‘H NMR (500 MHz, DMSO-r/6) S: 9.75 (s, 1H), 7.49 (d, J= 8.4 Hz, 2H), 7.08 (d, J= 8.4 Hz, 2H), 6.82 (t, J= 5.3 Hz, 1H), 3.14 – 3.04 (m, 2H), 2.80 (d, J= 11.4 Hz, 2H), 2.62 (t, J= 7.5 Hz, 2H), 2.23 (ddd, J= 15.5, 7.8, 4.1 Hz, 1H), 2.15 (s, 3H), 1.91 – 1.79 (m, 2H), 1.66 (ddd, J= 17.6, 15.5, 6.7 Hz, 4H), 1.36 (s, 9H).

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; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
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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. 162787-61-3, name is 2-(Methylsulfonamido)benzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 162787-61-3

O-Benzoic acid methanesulfonamide (0.060g, 0.28 mmol), HATU(0.213g, 0.56 mmol), and pyridine(68ul, 0.84 mmol), were dissolved in anhydrous DMF (8 ml). The reaction was stirred under nitrogen for 2 hours to activate the acid. When activation was approximately 80% complete by LC/MS (2 hr) the piperidine intermediate 28 (0.073g, 0.28 mmol), along with DIPEA (96ul, 0.56mmol) were added dissolved in DMF(4 ml). The reaction was stirred overnight while monitoring by LC/MS. Solvents were removed by rotary evaporation. The residue was taken up in DCM (100 ml)and washed with water (5 x 100 ml). The organic layer was collected, dried over MgS04, filtered and evaporated. The residue was taken up in DCM and columned on silica gel using a gradient of 0 to 10% MeOH : DCM to afford compound 26 (65 mg, 0.143 mmol, 51 %).1H-NMR (CD3CN, 300 MHz): delta 1.58 (m, 2H), 1.75 (m, 2H), 2.22 (s, 1H), 2.40 (s, 3H), 2.42 (s, 1H), 2.44 (s, 3H), 3.01 (m, 4H), 3.39 (m, 3H), 6.20 (s, 1H), 6.37 (m, 1H), 7.25-7.60 (m, 4H), 8.36 (bs, 1H).

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; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
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Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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. HPLC of Formula: C9H10ClNO2

General procedure: A mixture of 2-chloro-N-(4-chlorobenzyl)acetamide 3a (0.22 g, 1.0 mmol), 4-hydroxy-N-phenethyl-benzenesulfonamide 7a (0.42 g, 1.5 mmol), K2CO3 (0.21 g, 1.5 mmol) and KI (33 mg, 0.2 mmol) in acetone (20 ml) was stirred at 60 C for 7.0 h. After the organic solvent was evaporated, the residual was diluted with water (20 ml), extracted with dichloromethane, washed with brine and then dried over Na2SO4. After filtration and condensation, the crude product was obtained and recrystallized in ethyl acetate/hexane (1:1, v: v) to afford 1a as white solid (0.19 g, yield 42%). SAPA 1v was prepared by the reaction of 2-chloro-N-(3-methoxyphenyl)acetamide 3q with 7a according to the procedure described for SAPA 1a. Yield 46%; mp 107.0-108.0 C. ESI-MS m/z 441.3 (M+H)+. HRMS (ESI) of C23H24N2O5S (M+H)+ calcd, 441.1479; found, 441.1479. 1H NMR (400 MHz, DMSO-d6) delta 10.13 (s, 1H), 7.71 (d, J = 8.7 Hz, 2H), 7.57 (s, 1H), 7.30 (s, 1H), 7.28-7.10 (m, 9H), 6.65 (d, J = 7.9 Hz, 1H), 4.79 (s, 2H), 3.70 (s, 3H), 2.91 (s, 2H), 2.65 (t, J = 7.5 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 166.4, 161.1, 160.0, 140.0, 139.2, 133.2, 130.1, 129.1, 128.8, 126.7, 115.5, 112.4, 109.7, 105.9, 67.5, 55.5, 44.6, 35.7. HPLC purity: tR = 8.100, 98.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17641-08-6, its application will become more common.

Reference:
Article; Li, Ya-Li; Qi, Xiang-Yu; Jiang, Hui; Deng, Xiao-Dong; Dong, Yan-Ping; Ding, Ting-Bo; Zhou, Lu; Men, Peng; Chu, Yong; Wang, Ren-Xiao; Jiang, Xian-Cheng; Ye, De-Yong; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6173 – 6184;,
Amide – Wikipedia,
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Synthetic Route of 83948-53-2, A common heterocyclic compound, 83948-53-2, name is tert-Butyl N-(3-Bromopropyl)carbamate, molecular formula is C8H16BrNO2, 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.

Sodium carbonate (5.65 g, 40.9 mmol) was added to a solution of 4-iodophenol 5 (3.00 g, 13.6 mmol) in anhydrous acetonitrile (100 mL). The reaction was refluxed for 1 hour and the bromo derivative 4 (2.60 g, 10.9 mmol) was then added to this suspension. The reaction mixture was refluxed for 12 hours. The reaction progress was monitored by TLC. After this period, the reaction was complete. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Water (100 mL) was added to this residue, and the mixture was extracted with dichloromethane (2¡Á50 mL). The organic phases were combined, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by chromatography on a column of silica (dichloromethane) to give compound 6b in the form of a white solid (3.10 g, 75%). m.p.: 79-80 C. 1H NMR (500 MHz, CDCl3) delta: 7.52 (d, J=8.9 Hz, 2H), 6.64 (d, J=8.9 Hz, 2H), 4.69 (s, 1H), 3.95 (t, J=6.2 Hz, 2H), 3.29 (td, J=6.2; 6.2 Hz, 2H), 1.94 (m, J=6.2 Hz, 2H), 1.41 (s, 9H), 13C NMR (125 MHz, CDCl3) delta: 158.7; 155.9; 138.2; 116.9; 82.9; 65.9; 37.9. HMRS (ESI) calculated for C14H20NO31 [M+H+], m/z 378.0561. found: 378.0559.

The synthetic route of 83948-53-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CISBIO BIOASSAYS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; ECOLE NORMALE SUPERIEURE DE LYON; Lamarque, Laurent; Maury, Olivier; Parker, David; Zwier, Jurriaan; Walton, James W.; Bourdolle, Adrien; US2014/336373; (2014); A1;,
Amide – Wikipedia,
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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 6228-73-5 as follows. Quality Control of Cyclopropanecarboxamide

Cyclopropanecarboxamide (22.5 mg, 0.26 mmol) was combined with Int3 (30 mg, 0.088 mmol). Dimethylacetamide (DMA, 0.6 mL) was added to the vessel, followed by the addition of tris (diphenylmethyleneacetone) dicum (0) (Pd2dba3, 8.1 mg, 0.0088 mmol)4,5-bis (diphenylphosphino) -9,9-dimethyl(Xantphos, 10 mg, 0.018 mmol) and cesium carbonate (115 mg, 0.35 mmol). The vessel was then evacuated and backfilled three times with nitrogen and heated to 145 & lt; 0 & gt; C for 1 hour.The reaction was cooled to room temperature and then diluted with ethyl acetate (EtOAc, ca. 250 mL). The solution was washed twice with water, dried over sodium sulfate (Na2SO4), filtered, concentrated and purified using preparative HPLC. The product in the form of TFA salt was collected and then dissolved in about 15 mL of water, to which about 100 mL of saturated sodium bicarbonate (NaHCO3, an aqueous solution) was added and stirred for 10 minutes. The product of (x3) was extracted from the slurry using dichloromethane (DCM), dried over sodium sulfate, filtered, concentrated and collected to give 16.3 mg of 1 (48% yield).

According to the analysis of related databases, 6228-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN,, RYAN M.; WEINSTEIN,, DAVID S.; WROBLESKI,, STEPHEN T.; ZHANG,, YANLEI; TOKARSKI,, JOHN S.; MERTZMAN,, MICHAEL E.; LIU,, CHUNJIAN; (124 pag.)TWI582077; (2017); B;,
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Electric Literature of 226260-01-1, 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. 226260-01-1, name is 3-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 5 1-(3-FLUOROPHENYL) BUTAN-1-ONE To a solution of 3-fluoro-N-methoxy-N-methylbenzamide (130 mg, 0.71 mmol) in dry THF (2 mL) cooled to-10 C was added propyl magnesium chloride (532 ul, 2M solution in ether, 1.1 mmol) under nitrogen. The solution was stirred at-10 C for Ih and at room temperature for 75 min. The solution was the poured into saturated aqueous ammonium chloride and the product extracted into ethyl acetate (3 x 25 mL). The organic layers were combined, washed with brine, dried (MGSO4) and concentrated to give a pale yellow oil, which was purified by chromatography using ethyl acetate-hexane (1: 9) to separate the pure product (78 mg, 66%). ‘H-N. m. r. (CDCl3) No. 1.01 (t, =7. 4Hz, 3H, Me), 1.77 (sep, 2H, CH2CH3), 2.93 (T, J=7. 2Hz, 2H, COCH2), 7.15-7. 30 (m, 1H, Ar), 7.35-7. 50 (m, 1H, Ar), 7.60-7. 70 (m, 1H, Ar), 7.70-7. 80 (m, 1H, Ar.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-N-methoxy-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CYTOPIA PTY LTD; WO2004/52868; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics