Tag: M.W=200-300

25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide

Sodium hydride in mineral oil (21.40 mg, 0.535 mmol) was added to a, stirring, ice-bath cooled solution of 3-[4-(4,5-dimethyl-1 H-imidazol-1 -yl)phenyl]-1 , 4-diazaspiro[4.4]non-3- en-2-one (D28) (150 mg, 0.486 mmol) in DMF (5 ml) under argon. After stirring for 30 min. a solution of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (137 mg) in DMF (3 ml) was added over 1 h using a syringe pump maintaining an ice-bath temperature. The resulting reaction mixture was allowed to come to room temperature then stirred for a further 4 h. The reation mixture was diluted with methanol (20 ml) and applied to an SCX column (1Og). After washing with MeOH (50 ml) the product was eluted with 2M NH3-MeOH. Evaporation of the solvent afforded a brown gum. On dissolving in 1 :1MeOH:DMSO for MDAP purification a small amount of white solid precipitated. This was collected, washed with diethyl ether and dried The material was reapplied to an SCX column (1g) in MeOH (10 ml), washing (30 ml MeOH) and eluting as described above to remove residual DMSO. Drying afforded the free-base of the title compound as a white solid (20 mg).1H NMR (CDCI3) delta: 1.80 – 2.15 (8H, bm), 2.17 (3H, s, overlapping with adjacent bm), 2.25 (3H, s), 4.30 (2H, s), 7.40 (4H, m), 7.58 (1 H, s), 7.68 (1 H, d), 7.84 (1 H, s), 8.57 (2H, d),9.32 (1 H, s).Mass Spectrum (Electrospray LC/MS): Found 510 (MH+). C27H26F3N5O3 requires 509. Ret. time 1.81 min.A solution of the free-base (20 mg) in DCM (2 ml) was treated with an excess of 1 M HCI in diethyl ether (0.12 ml, 0.120 mmol). The volatiles were removed in vacuo and the residue dried under high vacuum at 550C to afford the title hydrochloride as a pale yellow solid (20 mg).Mass Spectrum (Electrospray LC/MS): Found 510 (MH+). C27H26F3N5O3 requires 509. Ret. time 1.77 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
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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. 636-76-0, name is 3-Sulfamoylbenzoic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Sulfamoylbenzoic acid

To 3-aminosulfonylbenzoic acid (4.0g), N,N-dimethylformamide (53 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.8 g), 1-hydroxybenzotriazole (2.7 g), N,O-dimethylhydroxylamine hydrochloride (1.9 g), and triethylamine (2.8 ml) were added under ice cooling and the mixture was stirred at room temperature for 12 hours. A potassium hydrogensulfate aqueous solution and ethyl acetate were added to the reaction solution and the mixture was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was successively washed with distilled water, saturated sodium hydrogencarbonate aqueous solution, and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2). To the obtained N-methoxy-N-methyl-3-aminosulfonylbenzamide (1.8 g), tetrahydrofuran (36 ml) and ethyl magnesium bromide (0.89M tetrahydrofuran solution, 41 ml) were added under ice cooling, the mixture was stirred at room temperature for 3 hours, then saturated ammonium chloride aqueous solution and ethyl acetate were added to reaction solution, the mixture was separated, then organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1). To the obtained 3-propionylbenzenesulfonamide (0.97 g), ethanol (2.5 ml), sodium acetate (0.56 g), and hydroxylamine hydrochloride (0.35 g) were added and the mixture was stirred at 90C for 3 hours. Ethyl acetate and water were added to the reaction solution, the mixture was separated, then the organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained 3-(N-hydroxypropanimidoyl)benzenesulfonamide was used instead of the starting material compound of Reference Example 109, that is, 1-(4-aminophenyl)propan-1-on oxime, for the similar procedure as with Reference Example 109 to obtain the title compound. NMR (DMSO-d6): delta8.50-8.36(3H, br), 7.92(1H, s), 7.83(1H, d, J=7.5Hz), 7.71-7.60(2H, m), 7.42(2H, s), 4.33-4.21(1H, br), 2.00-1.70(2H, m), 0.75(3H, t, J=7.4Hz) MS: 215(M+H)+

The synthetic route of 636-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); A1;,
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Reference of 17400-34-9,Some common heterocyclic compound, 17400-34-9, name is Benzyl (3-aminopropyl)carbamate hydrochloride, molecular formula is C11H17ClN2O2, 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.

Intermediate 5 Benzyl N-r2-(pent-4-vnamido) propyll carbamate Pentynoic acid (0.267 g, 2.72 mmol) was added to a suspension of Z-propandiamine hydrochloride ( 1 g, 4 mmol), EDCI- HCI 767 mg, 4 mmol) a nd HOBt. H20 (540 mg, 4 mmol) in dry DCM (20 ml_) . The resulting mixture was cooled at 0C a nd TEA ( 1.12 ml_, 8 mmol) was added dropwise. The reaction mixture was stirred at 25C for 16h. The DCM solution was washed with NH4CI solution (20 ml_ x 2) and NaHC03 solution, the organic phase was filtered through a phase separator and evaporated to dryness to obta in the title compound as a white solid (800 mg) . The crude product was used in the next step without further purification . JH NMR (400 MHz, CDCI3) delta 7.41-7.31 (m, 5H), 6.20 (br s, 1 H), 5.27 (br s, 1 H), 5.12 (s, 2H), 3.34 (q , 2H), 3.27 (q , 2H), 2.59-2.52 (m, 2H), 2.42 (t, 2H), 2.02 (br s, 1 H) . UPLC-MS Rt=0.76; m/z (ES+) : 289 [M + H] + .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzyl (3-aminopropyl)carbamate hydrochloride, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; S?RENSEN, Morten, Dahl; DI FABIO, Romani; POZZAN, Alfonso; CATALANI, Maria, Pia; BLADH, Haakon; FELDING, Jakob; WO2013/124286; (2013); A1;,
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Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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 R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide

EXAMPLES Example 1 Preparation of (R)-2-bromo-N- [2- (4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl] – acetamide) 1.0 g of (R)-2- (4-methoxyphenyl-3-aminosulfonyl-phenyl)-1-methylethylamine was dissolved in 50 ml of methylene chloride. 0.72 g (2.0 eq) of triethyamine was added to the resultant solution and cooled to 0 to 5C. Then, 1.44 g (2.0 eq) of bromoacetyl bromide was added dropwise to the resultant solution and stirred at 0 to 5C. After it was confirmed by HPLC that the starting materials were completely consumed, 100 ml of ethyl acetate and then 50 ml of 10% HCI were added to the resultant solution and stirred. The ethyl acetate layer was separated and washed with 50 ml of a 10% K2CO3 solution and dried over MgS04, and then, filtered and concentrated. The obtained concentrate was dissolved in ethyl acetate and recrystallized with hexane to obtain the title compound (1.2 g). Yield : 80.0% NMR (DMSO-d6) : 1.15 (3H, d), 2. 6-2. 8 (2H, m), 3.8 (2H, s), 3.90 (4H, s), 7.0 (2H, s), 7.1 (1H, d), 7.4 (1H, d), 7.6 (1H, d), 8.21 (2H, d). [a] 24D = + 5.0 (C=1, MeOH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 112101-81-2, its application will become more common.

Reference:
Patent; CJ CORPORATION; WO2005/56521; (2005); A1;,
Amide – Wikipedia,
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Related Products of 33045-52-2, 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. 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) 2-Methoxy-5-sulfamoylbenzoic acid. Methyl 2-methoxy-5-sulfamoylbenzoate(4.91g, 20mmol) was dissolved in methanol(30mL). 2N Aqueous sodium hydroxide(30mL, 60mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, and the separated solid was filtered to give the title compound(4.55g, 98.3%) as a white solid. 1H-NMR(DMSO-d6): delta 3.89(3H, s), 7.30(1H, d, J=8.7Hz), 7.32(2H, s), 7.92(1H, dd, J=8.7, 2.7Hz), 8.09(1H, d, J=2.7Hz), 13.03(1H, br).

The synthetic route of Methyl 2-methoxy-5-sulfamoylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1512396; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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 127828-22-2, Product Details of 127828-22-2

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate was then taken up in CH2Cl2 (20 mL) along with salicylic acid (576 mg, 4.17 mmol) and EDCI (905 mg. 4.72 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-(2-hydroxybenzamido)ethoxy)ethylcarbamate (450 mg, 33%). Mass calculated for C16H24N2O5: 324.17; found: [M+H]+=325.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82192; (2011); A1;,
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Application of 16313-66-9, A common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 dry 50 mL flask was charged with 2-aminobenzamides 1 (1.1 mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (0.280 g, 1.0 mmol), iodine (0.026 g, 0.01 mmol) and toluene (10.0 mL). The mixture was stirred at 80 C until the reactant 1 was consumed. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:3) as the eluent to give products 5.

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; Lu, Lian; Zhang, Mei-Mei; Jiang, Hong; Wang, Xiang-Shan; Tetrahedron Letters; vol. 54; 8; (2013); p. 757 – 760;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7326-73-0, name is 3-(N,N-Dimethylsulfamoyl)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. Recommanded Product: 3-(N,N-Dimethylsulfamoyl)benzoic acid

To a solution of 3-(dimethylsulfamoyl)benzoic acid (38.30 mg, 167.06 gmol) in DCM (1 .0 ml_) were added HATU (69.87 mg, 183.76 gmol), DIEA (64.77 mg, 501 .18 gmol, 87.30 gl_) and intermediate i- 45b (100 mg, 167.06 gmol). The reaction mixture was stirred at 20 C for 12 hours and then poured into water (2.0 ml_). The solution was extracted with EtOAc (2.0 ml_ * 3). The combined organic extracts were washed with brine (5.0 ml_), dried over Na2SC>4 and filtered. The filtrate was concentrated to give a residue. The residue was purified by column chromatography (S1O2. PE/EA=50/1 -1 /1 ) to give intermediate i-45c as a white solid. LCMS (ESI) m/z: [M+H]+ = 696.0 Chiral HPLC: OJ-3-MeOH(DEA)-60-7MIN-3ML-35T, 5.276min.

The synthetic route of 7326-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
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Related Products of 51-06-9,Some common heterocyclic compound, 51-06-9, name is 4-Amino-N-(2-diethylaminoethyl)benzamide, molecular formula is C13H21N3O, 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 V 4-[(Butylsulfonyl)amino]-N-[2-(diethylamino)ethyl]benzamide hydrobromide To 100 ml of methylene chloride add 6.52 g (36.2 mmole) of 4-amino-N-[2-(diethylamino)ethyl]benzamide and cool to -78 C. under nitrogen atmosphere. To this solution slowly add 5.61 g (36.2 mmole) of n-butanesulfonyl chloride. When the addition is complete, allow the reaction mixture to warm to room temperature and monitor by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Upon completion of the reaction remove the solvent in vacuo. To the resulting oil add 50 ml H2 O followed by 50% sodium hydroxide until pH=14. Extract the aqueous layer with 3*50 ml diethyl ether and 2*25 ml of methylene chloride. To the aqueous layer add concentrated HCl to bring the pH to 8.5. Extract the aqueous solution with 3*75 ml of methylene chloride. Combine the extracts and dry over sodium sulfate. Filter the drying agent and remove the solvent in vacuo. Dissolve the resulting oil in acetonitrile. Bubble HBr gas through the solution until pH=1. Remove the solvent in vacuo. Triterate the resulting oil in diethyl ether and ethyl acetate to yield a precipitate. Isolate by filtration and recrystallize from MeOH/ethyl acetate to afford the title compound. NMR (DMSO-d6): delta=0.82(t,3), 1.22(t,6), 1.34(m,2), 1.63 (m,2), 3.23(m,8), 3.57(m,2), 7.26 (d,2), 8.67(t,1), 9.22(br s,1) and 10.19(s,1)ppm.

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

Reference:
Patent; Schering A.G.; US4629739; (1986); 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 54616-47-6 as follows. category: amides-buliding-blocks

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 ¡Á 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

According to the analysis of related databases, 54616-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
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