Tag: M.W=200-300

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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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;,
Amide – Wikipedia,
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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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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;,
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Related Products of 239074-29-4,Some common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, 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.

Alcohol (79.5 g, 347 mmol) was dissolved in tetrahydrofuran (800 ml). Triethylamine (72.5 ml, 520 mmol) and methanesulfonyl chloride (32.2 ml, 416 mmol) were sequentially added thereto under ice-cooling with stirring and the mixture was reacted for 1.5 hour. The reactant was poured into aqueous citric acid (citric acid monohydrate 30 g in water 500 ml) to become pH 4 and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure. The crystal deposited in the removal process was collected by filtration and washed with hexane to give mesylate (100 g). The obtained mesylate was dissolved in dimethylformamide (100 ml) and sodium azide (63.7 g, 980 mmol) was added thereto and reacted at 80 C. for 2 hours. The reactant was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure to quantitatively give the desired Azide (the crude weight is 85.4 g).1H-NMR (DMSO-d6) delta ppm: 0.90-1.21 (m, 4H), 1.32-1.50 (m, 1H), 1.37 (s, 9H), 1.65-1.84 (m, 4H), 3.06-3.24 (m, 3H), 6.71 (d, 1H, J=8.1 Hz).

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; US2010/273841; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, 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 147291-66-5, name: tert-Butyl 3-aminobenzylcarbamate

2-chloro-ethyl[3-(tert-butoxycarbonylamino-methyl)-phenyl]-carbamate 900 mg g (3.48 mmol) tert-butyl 3-amino-benzyl)-carbamate are liberated as the base, then placed in 40 ml of tetrahydrofuran, and 1.11 ml (8 mmol) triethylamine and 0.75 ml (6.82 mmol) 2-chloroethylchloroformate are added. The reaction mixture is stirred for 16 hours at ambient temperature, then extracted with dichloromethane and water. The organic phase is separated off using a phase separation cartridge and evaporated to dryness. Yield: 1.20 g (100% of theoretical)

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 3-aminobenzylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Brandl, Trixi; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Breitfelder, Steffen; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238746; (2007); A1;,
Amide – Wikipedia,
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Electric Literature of 956434-30-3, A common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, molecular formula is C13H17ClN2O3, 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.

(step 1) To a solution of 1-cyclopentylethanol (0.22 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 100C for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100C for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?40% ethyl acetate/hexane) to give tert-butyl 8-(l-cyclopentylethoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.45 g, 70%) as a white powder. 1H-NMR(CDCl3):delta1.27(3H,t,J=6.0Hz), 1.25-1.85(8H,m), 1.43(9H,s), 2.00-2.12(1H,m), 3.80-3.82(2H,m), 4.21(2H,brs), 4.33-4.45(2H,m), 5.01(1H,brs), 6.38(1H,d,J=8.1Hz), 7.30-7.50(1H,m)

The synthetic route of 956434-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2213675; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, 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. Quality Control of 4-(2-Aminoethyl)benzenesulfonamide

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0¡ãC, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

The synthetic route of 35303-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
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Related Products of 112253-70-0,Some common heterocyclic compound, 112253-70-0, name is 2-Amino-4-bromobenzamide, molecular formula is C7H7BrN2O, 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.

Oxalyl chloride (2.9 mL, 33 mmol) was added drop wise to the mixture of compound PR-1 (5 g, 22 mmol), 2-amino-4-bromobenzamide (4.7 g, 22 mmol) and pyridine (50 mL). The mixture was stirred for 1 hour at room temperature. The solvent was removed in vacuo. The obtained residue was purified by chromatography (petroleum ether: acetate ether=5: l) resulting in a intermediate (3.6 g). Method A2; Rt: 1.15 min. m/z=:447.7 (M+Na)+ Exact mass: 425.1 The above obtained intermediate (3.6 g,), Na2C03 (2.7 g. 25.4 mmol), H20 (20 mL) and CH3CH2OH (20 mL) were stirred for 2 hours under reflux. Most of CH3CH2OH was removed in vacuo. The residue was extracted with ethyl acetate (3 x 20 mL). The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was washed with t-butyl methyl ether resulting in compound QA-6 (3.4 g)

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-bromobenzamide, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2013/98313; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics