Tag: M.W=200-300

Synthetic Route of 35303-76-5, The chemical industry reduces the impact on the environment during synthesis 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of 4-(2-aminoethyl)benzenesulfonamide (80 mg, 0.40 mmol), AcOH (0.05 mL) and di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3- oxopropyl)heptanedioate (447 mg, 0.81 mmol) in DCE (20 mL) was stirred at 80 °C for 30 min under nitrogen. The reaction mixture was cooled to 0 °C, and treated with NaBH(QAc)3 (0,254 g, 1 ,2 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by biotage over silica gel to afford the desired product (322 mg, 63percent). NMR (400 MHz, DMSO-d6) 7.77 (s, 2 H), 7.64 (d, J – 8.0 Hz, 2 H), 7.23 (s. 2 H), 7.21 (d, J = 8.4 Hz, 2 H), 7.01 (s, 2 H), 6.80 (s. 2 H), 4.57 (s. 4 H), 3.61 (s, 4 H), 2.79-2,62 (m, 4 H), 2,09 (t, J = 8.0 Hz, 12 H), 1.76 (t, J = 8.0 Hz, 12 H), 1.32 (s, 54 H); MS (ESI), 636.5 (M/2+H)+.

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, 4-(2-Aminoethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOLECULAR INSIGHT PHARMACEUTICALS; BABICH, John, W; ZIMMERMAN, Craig; JOYAL, John; LU, Genliang; HILLIER, Shawn; MARESCA, Kevin, P; MARQUIS, John; WO2013/103813; (2013); 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. 437998-34-0, name is 2-Amino-3-bromobenzamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7BrN2O

General procedure: 2-Aminobenzamides (1 mmol) and 1,1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.

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; Zhu, Fengjuan; Song, Runjiang; Li, Shen; Shao, Xusheng; Synlett; vol. 27; 14; (2016); p. 2167 – 2170;,
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Reference of 123986-64-1, 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 123986-64-1 as follows.

General procedure: The solution of (R)-1-(6-(4-(1-(3-hydroxybenzyl)-3-methyl-1H-thieno[2,3-c]pyrazole-5-carbonyl)-2-methylpiperazinmethylpiperazin-1-yl)pyridin-3-yl)ethanone (9b) (0.059 g, 120 mumol) in THF (1.0 mL)was added to tert-butyl(2-hydroxyethyl)carbamate (29.0 mg, 180 mumol), polymer supported PPh3(3 mmol/g, 120 mg) and di-2-methoxyethyl azodicarboxylate (0.051 g, 216 mumol).The mixture was stirred at room temperature for 2 h. Then, polymer supportedPPh3 (3 mmol/g, 60 mg) and the solution of di-2-methoxyethylazodicarboxylate (0.051 g, 216 mumol) in THF (0.10 mL) were added to thereaction mixture. The mixture was stirred at room temperature for 1 h. Thesolvent was evaporated by blowing away with the air at 50 C. The residue waspoured into toluene (3.0 mL) and water (1.0 mL), and stirred for 5 min. Theorganic layer was filtered on Top-Phase Separation Filter Tube, and thefiltrate was evaporated by blowing away with the air at 60 C. The residue waspurified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3aq. 10:90?100:0). Pure fractions were combined and concentrated byblowing away with the air at 50 C. The intermediate was dissolved into EtOAc(0.50 mL) and 4M HCl-EtOAc (1.0 mL) was added to the solution at room temperature.The mixture was shaken at room temperature for 10 min. Then the mixture wasevaporated by blowing away with the air at 50 C. The solution of BODIPY FLpropionic acid 1 (0.020 g, 69 mumol)in DMA (0.50 mL) and the solution of WSC(HCl) (0.016 g, 84 mumol) and HOBt(0.011 g, 84 mumol) in DMA (0.500 mL) and iPr2NEt(84 mL, 480 umol) were added to the mixture. The mixturewas stirred at room temperature for 2 h. The reaction mixture was diluted withEtOAc (3.0 mL) and quenched with water (1.0 mL), and stirred for 2 min. Theorganic layer was separated and then the aqueous layer was extracted with EtOAc(2.0 mL). The combined organic layer was evaporated by blowing away with theair at 50 C. The residue was purified by preparative HPLC (Actus Triart C18,eluted with MeCN/10 mM NH4HCO3 aq. 5:95?100:0). Purefractions were combined and concentrated by blowing away with the air at 50 Cto give the product 10 (8 mg, 9.9 mmol, 1 %).

According to the analysis of related databases, 123986-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Katoh, Taisuke; Yoshikawa, Masato; Yamamoto, Takeshi; Arai, Ryosuke; Nii, Noriyuki; Tomata, Yoshihide; Suzuki, Shinkichi; Koyama, Ryoukichi; Negoro, Nobuyuki; Yogo, Takatoshi; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1145 – 1148;,
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Related Products of 123986-64-1, These common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, 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.

1) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-benzylpiperidine To a solution of 5.0 g (21.07 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]-1-phenylmethanol and 5.9 ml (42.33 mM) of triethylamine in THF (42 ml) was added 2.5 ml (32.3 mM) of methanesulfonyl chloride at 0 C. and the mixture was stirred at the prevailing temperature for one hour. The reaction was stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 7.21 g (21.07 mM) of crude product as light-brown solid. To a solution of 7.21 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 g (42.33 mM) of triethylamine as well as 3.69 g (21.05 mM) of 4-phenylpiperidine and the mixture was refluxed for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow oil. Yield 5.77 g (69%) 1H-NMR (200 MHz, CDCl3) delta: 1.20-1.40 (2H, m), 1.46 (9H, s), 1.85-2.01 (2H, m), 2.53 (2H, d, J=6.2 Hz), 2.78-2.93 (2H, m), 3.48 (2H, s), 4.29 (2H, d, J=6.0 Hz), 4.70-4.88 (1H, m), 7.07-7.34 (9H, m). IR (neat): 3350, 2924, 1709, 1508, 1452, 1365, 1252, 1173 cm-1.

The synthetic route of 123986-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
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A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, 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. 108468-00-4.

General procedure: A solution of 4-(Boc-aminomethyl)benzylamine (3) (1.0 mmol) and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with an ice bath, then the corresponding sulfochloride (1.1 mmol, dissolved in 2 mL anhydrous DCM) was added dropwise. The reaction mixture was allowed to stir at 0 C for 1 h. After removing the cooling bath, the resulting mixture was stirred for 5 h at room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10 mL) for three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (150:1, v/v) to give the product as a white solid.

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Gurbani, Saumya; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 360 – 371;,
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Reference of 6325-93-5,Some common heterocyclic compound, 6325-93-5, name is 4-Nitrobenzenesulfonamide, molecular formula is C6H6N2O4S, 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: The catalytic reduction of nitro aromatics was conducted in a 25 mlTelfon-lined stainless steel autoclave with magnetic stirring. In a typicalprocess, 6 mmol nitroarene, and desired amounts of reducing agent andsolvents were introduced in the reactor. The autoclave was transferredinto a water bath at the set temperature with an accuracy of better than0.2 C for ?0.5 h. Then, 10 mg catalyst was added into the reactionmixture and started the reduction at a stirring rate of 450 rpm. After thereaction, the catalyst was rapidly separated by ltration. n-Decane(500 muL) as standard was added into the ltrate and was dried withanhydrous Na 2 SO 4 . The products were analyzed by gas chromato-graphy-mass spectrometry (GC-MS) (Shimadzu GCMS-QP2010 Plus)and GC (Varian CP-3800) with a capillary column (column VF-1 ms,15 m, 0.25 mm, 0.25 mum) and a ame ionization detector (FID).

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

Reference:
Article; Huang, Haigen; Liang, Xiangcheng; Wang, Xueguang; Sheng, Yao; Chen, Chenju; Zou, Xiujing; Lu, Xionggang; Applied Catalysis A: General; vol. 559; (2018); p. 127 – 137;,
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Application of 40724-47-8,Some common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, molecular formula is C7H8BrNO2S, 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.

4-Azidomethyl-benzenesulfonamide (INT-2); To a stirred solution of 4-bromomethyl-benzenesulfonamide (4.500 g,17.9917 mmol) (prepared from 4-bromomethyl-benzenesulfonyl chloride upon treatment with ammonia (as described by Yee YK et al. in Journal of Medicinal Chemistry 1990 33 (9) 2437-2451 ) in lambda/,lambda/-dimethylformamide (30 ml), sodium azide is added (1 1 .696 g, 179.917 mmol) and the reaction mixture is heated at 900C for 14 hours under a nitrogen atmosphere. The suspension is filtered, to remove the excess of sodium azide, and the solid residue is washed with ethyl acetate (4 x 50 ml). The mother liquids are concentrated, to afford a crude yellow liquid (3.820 g, 100% mass balance), that is used as such for the next step. IR: 2098.8 cm”1.

The synthetic route of 40724-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2009/112459; (2009); A1;,
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Application of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-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.

To a solution of 2-amino-5-bromo-benzamide (29.2 g, 136 mmol) andtriethylamine (25.0 mL, 173 mmol) in THF (500 mL) was added dropwise o-anisoyl chloride (24.0 g, 140 mmol). Stirring at room temperature was continued for 3 h, after which the formed precipitate was filtered and washed once with THF and twice with dichloromethane yielding 2-(o-anisoyl)-amino-5-bromo-benzamide (51.4 g, 84%) with 1 equivalent of triethylamine hydrochloride.

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-5-bromobenzamide, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/28904; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 703-12-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 703-12-8 name is 4-Bromo-N-methylbenzenesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step b: 4-(lambdar-Methylsulfamoyl)phenylboronic acid; To a solution of 4-bromo-iV-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(O1Pr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at -70 0C. The mixture was slowly warmed to 0 0C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(iV-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-J6, 300 MHz) delta 8.29 (s, 2 H), 7.92 (d, J = 8.1 Hz, 2 H), 7.69 (d, J = 8.4 Hz, 2 H), 2.36 (d, J = 5.1 Hz, 3 H).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56341; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 4793-24-2, These common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, 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.

Compound 1 was dissolved in 1 mL of compound 2 and heated to 10OC and monitored by TLC until complete. When complete, as indicated by TLC, the reaction was removed from the heat. A pale yellow goo remained, containing crystals. To this mixture was added IM HCl and this stirred for 10 min. At this time, a precipitate fell out of solution that was subsequently filtered to yield the pure product as indicated by NMR.IH NMR: 8.25 (s, IH), 7.5-7.2 (m, 5H), 6.71 (s, IH), 4.54 (s, 2H), 4.0 (s, IH), 3.3 (s, 2H).Ms API-ES Neg. Scan calculated for C14H12C1N2O4S- 339.02. ; obtained 339.2

The synthetic route of 4793-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLYNN, Gary, A.; YOOL, Andrea, J.; MIGLIATI, Elton, Rodrigues; RITTER, Leslie, S.; WO2008/52190; (2008); A2;,
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Amide – an overview | ScienceDirect Topics