Tag: M.W=200-300

127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, 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. COA of Formula: C12H12N2O2S

To a suspension of 2,4-bis(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one (150 mg, 0.627 mmol) in isopropanol (4 mL) were added 4-amino-N-phenylbenzenesulfonamide (327 mg, 1.316 mmol) and 2 drops of conc. HCl, and the reaction mixture was stirred at reflux for 10 hours. The reaction mixture was cooled, diluted with MeOH (10 mL) and treated with aqueous NaHCO3 solution to adjust pH to 7. The precipitate was collected by filtration and washed with water, and purified using column chromatography (silica gel, 0 to 80% 3:1 DCM:MeOH/DCM) to give 190 mg of product as a pale brown solid. MS (ES) m/z = 440.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 2.53 (s, 3H), 6.36 (d, J = 7.34 Hz, 1H), 7.01 – 7.16 (m, 3H), 7.20 – 7.28 (m, 2H), 7.60 (d, J = 7.34 Hz, 1H), 7.73 – 7.81 (m, 2H), 7.86 – 7.99 (m, 2H), 10.20 (br.s, 1H), 12.00 (br s, 1H), 12.25 (s, 1H); 13C NMR (101 MHz, DMSO-d6) delta ppm 14.22, 101.22, 105.88, 120.57, 121.12, 124.49, 128.44, 129.60, 134.23, 138.24, 138.31, 142.32, 158.91, 160.38, 163.83, 174.65. HRMS m/z calculated for C20H18N5O3S2 [M + H+]: 440.0851, found 440.0856.

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinrong; Suarez, Dominic P.; Li, William Hoi Hong; McSherry, Allison K.; Sanchez, Robert M.; Moore, Michael L.; Axten, Jeffrey M.; Tetrahedron Letters; vol. 60; 49; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, 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 104060-23-3, Safety of N-Boc-2-(4-Aminophenyl)ethanol

To a solution of tert-butyl (4-(2-hydroxyethyl)phenyl)carbamate (6.90 g, 30 mmol) and imidazole (2.45 g, 36 mmol) in DCM (100 mL), was added dropwise chlorotriisopropylsilane (6.36 g, 33 mmol) at rt. The reaction mixture was stirred for lh and then water was added. The organic layer was washed with brine dried over Na2504 and concentrated under vacuum. The residue was purified by column chromatography (silica gel, DCM) to afford tert-butyl (4-(2-((triisopropylsilyl)oxy)ethyl)phenyl)carbamate (11.7 g, 99%) as a white solid.

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, N-Boc-2-(4-Aminophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); A1;,
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Some common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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: C7H6F3NO2S

Accurate weighing of the quinoline nitrogen oxides (44.3 mg, 0 . 25mmol), 4 – trifluoromethylbenzene sulfonamide (55.0 mg, 0 . 25mmol), double (trifluoroacetic acyloxy) iodobenzene (107.2 mg, 0 . 25mmol), 4 – N – morpholine – phenyl diphenyl phosphine (100.9 mg, 0 . 75mmol), and in turn to 25 ml of the bottle in the Schlenk, adding refined over-dimethyl sulfoxide (3.0 ml), is 120 C in oil bath reaction 30h. After the reaction, the solvent is removed under reduced pressure, the use of petroleum ether/ethyl acetate as eluant, separating by silica gel column, 4 – Trifluoromethyl – N – (quinolin – 2 – yl) benzenesulfonamide of yield is 67%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 830-43-3, its application will become more common.

Reference:
Patent; Dalian University of Technology; Yu Xiaoqiang; Bao Ming; Feng Xiujuan; Zhang Yue; Guo Mingju; (19 pag.)CN104447536; (2017); B;,
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Electric Literature of 108468-00-4, 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 108468-00-4 as follows.

100 mg (0.109 mmol) of compound 3d was dissolved in 4 ml of DMF and cooled to -15 C. After addition of 36 tl (0.327 mmol) of NMM and 15 tl (0.109 mmol) CKIBE, the solution was stirred for 15 mm, followed by addition of 40mg (0.169 mmol) ofBoc-p-diaminoxylene and 12 tl (0.109 mmol) of NMM. The mixture was stirred for one hour at 0 C. and overnight at RT. The solvent was removed in vacuo, the residue was mixed with 1 ml 90% TFA and stirred for 2 h at RT. After removing the solvent in vacuo, the residue was dissolved in 8 ml of 30% B and purified by prep. HPLC (start at 10% B). Fractions containing the product were combined, the solvent was removed in vacuo and the residue dissolved in 80% t-butanol/water and lyophilized.jOllO] Yield: 39

According to the analysis of related databases, 108468-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHILIPPS-UNIVERSITAeT MARBURG; Steinmetzer, Torsten; Saupe, Sebastian; US2014/213781; (2014); 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. 83948-54-3, name is tert-Butyl (5-bromopentyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound 5-1 (0.95 g, 4.29 mmol) was dissolved in N, N-dimethylformamide,Join in sequence5- (tert-butoxycarbonylamino) bromopentane(1.7 g, 6.43 mmol)And potassium carbonate (1.78 g, 12.9 mmol) were reacted at 90 C for 6 hours,The solvent was evaporated under reduced pressure, and ethyl acetate (40 ml) and water (30 ml) were added. After extraction, the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and subjected to column chromatography to give compound 5-2 (1.6 g, Yield 89%).

The synthetic route of 83948-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; China Pharmaceutical University; Jiang Sheng; Tu Zhengchao; Zhu Jidong; Yao Hequan; Yao Yiwu; Tan Xiaochu; Gu Shoulai; Qiu Yatao; (30 pag.)CN106928192; (2017); A;,
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Application of 109903-35-7, A common heterocyclic compound, 109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, molecular formula is C8H12N2O2S, 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.

N-Methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride A solution of 2-chloro-4-phenylamino-quinazoline (0.92 g) (prepared as described in Example 1a and N-methyl-(4-aminophenyl)-methanesulfonamide (0.80 g) in 10 ml of isopentylalcohol is stirred under nitrogen at 170 C. for 15 min in a sealed vessel. The warm reaction mixture is diluted with 10 ml ethanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off to yield N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 259-263 C.; Rf (A2) 0.11, FAB-MS: (M+H)+ =420. Analytical data: C22 H21 N5 O2 S+HCl.

The synthetic route of 109903-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synaptic Pharmaceutical Corporation; US5968819; (1999); A;,
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. 46460-73-5, name is Benzyl (3-aminopropyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: Benzyl (3-aminopropyl)carbamate

More specifically, commercially available mono-Cbz (benzyloxycarbonyl) protected 1,3-diaminopropane (1 g, 4.08 mmol) was suspended in dry dichloromethane (10 mL). The reaction was cooled in an ice bath and sequentially treated with triethylamine (4.2 mmol, 0.58 mL) and 2-trimethylsilylethyl-N-succinimidyl carbonate (Teoc-Osu, 1.06 g, 4.1 mmol). After stirring at rt for 16 hr, the reaction was diluted with dichloromethane and extracted with 5percent HCl, saturated NaHCO3 solution, brine, dried (MgSO4) and concentrated. The crude residue obtained was dissolved in ethyl acetate (30 mL) and hydrogenated using 10percent Palladium/carbon using a hydrogen balloon. After 16 hr at room temp, the reaction was filtered through celite and the filter bed washed with additional ethyl acetate. The filtrate was concentrated and the crude residue was dissolved in a mixture of dichloromethane (10 mL) and methanol (30 mL). 3,5-Dibromobenzaldehyde (1.05 g, 4 mmol) and glacial acetic acid (1 mL) were added to the reaction. After stirring for 15 minutes at room temp, sodium cyanoborohydride (0.38 g, 6 mmol) was added to the reaction, which was stirred for an additional 16 h at room temp. The reaction was diluted with additional dichloromethane and the organic phase was sequentially washed with sat. NaHCO3 solution, brine, dried (MgSO4) and concentrated. The crude residue obtained was purified by chromatography on silica gel using ethyl acetate/hexanes. 1H NMR (300 MHz, CDCl3) delta 7.51 (s, 1H), 7.38 (s, 2H), 5.16 (s, br, 1H), 4.12 (t, 2H), 3.69 (s, 2H), 3.25 (m, 2H), 2.64 (t, 2H), 1.65 (m, 2H), 0.95 (t, 2H).

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; Seth, Punit P.; Robinson, Dale E.; Jefferson, Elizabeth Anne; Swayze, Eric E.; US2006/30603; (2006); A1;,
Amide – Wikipedia,
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Reference of 112101-81-2,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.

Into a 4-necked 500ml round bottom flask, equipped with Dean-stark apparatus, 150ml of toluene, 24.4gms (0.1mole) of (R)-5-(2-aminopropyl)-2-methoxy benzene sulfonamide of formula-IV and 12.2gms (1.1mole) of 4-hydroxybenzaldehyde are charged. The reaction was carried out azeotrophically and the water (1.8ml) collected and separated. Then the solvent is removed under vacuum at temp max 80C. Cooled to 25-30C. The vacuum is released under N2 atmosphere. A thick oily mass which solidified on storage which is the compound of 2-methoxy-5-(2R)-2-{[(1-E/Z-4-hydroxyphenylmethylene)amino]propyl} benzenesulfonamide of formula-IIIc (35.0gms). Recrystallized sample (from IPA) has the following characteristics. MR : 96-100C 1H [NMR : (200MHz, CDCl3+DMSO-d6) delta 1.23-1.26 (d, 3H), 2.84-2.87 (t, 2H), 3.43-3.52 (m, 1H), 3.92 (s, 3H), 6.0, (broad, 2H), 6.8-7.7 (aromatic, 7H), 7.95 (s, imine, 1H) IR (KBr), 3352, 3257, 2969, 1640, 1606, 1585, 1484, 1394, 1158, 1070, 1018 cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 143557-91-9, 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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Triphenylphosphine (3.57 g, 13.6 mmol) was solved in toluene (40 ml) and cooled to <;20C. Diethylazodicarboxylate (40% in toluene) (6.2 ml, 13.6 mmol) was added to the mixture below 20C, followed by stirring for 10 minutes, endo-3- Hydroxy-8-aza-bicyclo[3.2.1] octane-8-carboxylic acid te/t-butyl ester (2.58 g, 11.3 mmol) was added and after 10 minutes 7-hydroxy-3-methyl-chromen-2-one (2.0 g, 11.3 mmol) was added to the mixture. The temperature raised to 28C due to an exothermic reaction. The mixture was allowed to stir for 15 h at room temperature. Water (50 ml) and sodium hydroxide (20 ml, 0.1 M) was added followed by stirring. The mixture was filtered and washed with water and diethylether. Yield 2.50 g (57%). The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate. I believe this compound will play a more active role in future production and life. Reference:
Patent; NEUROSEARCH A/S; PETERS, Dan; NIELSEN, Elsebet, Østergaard; NIELSEN, Karin, Sandager; MUNRO, Gordon; WO2010/130620; (2010); 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. 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 830-43-3

EXAMPLE 159 Synthesis of 1-(2-chlorobenzyl)-2-methyl-6-[4-(trifluoromethyl)benzenesulfonylcarbamoyl]benzimidazole (221) In the same manner as in Example 158, 0.390 g of 1-(2-chlorobenzyl)-2-methyl-6-[4-(trifluoromethyl)benzenesulfonylcarbamoyl]benzimidazole (221) were formed from 0.450 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole, 0.486 g of N,N’-carbonyldiimidazole, 0.676 g of 4-(trifluoromethyl)benzenesulfonamide and 0.457 g of diazabicycloundecene.

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; Fujisawa Pharmaceutical Co., Ltd.; US6166219; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics