Month: September 2021

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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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Amide – an overview | ScienceDirect Topics

Electric Literature of 67442-07-3, 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 67442-07-3 as follows.

To a THF solution of (S)-1-bromo-2-methyloxy-3-(1-methyloxyheptyl)benzene (9, 12.5 g) obatined in the second step was added dropwise a 2M isopropyl magnesium chloride THF solution (44 mL) under ice-cooling. After the reaction solution was stirred at 45°C for 3 hours, N-methyloxy-N-methyl-2-chloroacetamide(10, 3.5 g) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was extracted with ethyl acetate, and purified by silica gel chromatography to obtain (S)-2-chloro-1-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)ethanone (11). NMR (CDCl3) delta ppm: 0.87 (3H, t, J = 6.8 Hz), 1.2 – 1.82 (10H, m), 3.22 (3H, s), 3.78 (3H, s), 4.53 (1H, m), 4.73 (2H, m), 7.24 (1H, t, J = 7.6Hz), 7.52 (1H, dd, J = 7.6 Hz, J = 1.8 Hz), 7.60 (1H, dd, J = 7.7 Hz, J = 1.8Hz)

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi&Co., Ltd.; EP2184279; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of tert-Butyl methyl(2-(methylamino)ethyl)carbamate

Brought 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione (1-3) (500 mg, 1.81 mmol) , tert-butyl methyl(2-(methylamino)ethyl)carbamate (22-1) (1.99 mmol) and DIEA (787 4.52 mmol) up in NMP (3.62 mL ) and heated to 90°C overnight. Cooled the mixture to r.t. and loaded directly onto reversed phase isco 10-100percent ACN/water w TFA. Lyophilized the combined fractions to give tert-butyl (2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4- yl)(methyl)amino)ethyl)(methyl)carbamate (800 mg, 1.79 mmol, 99.5 percent) as a yellow solid. LC/MS (ES+): m/z 467 [M+Na]+

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 193751-54-1, 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 193751-54-1 as follows.

To a solution of N-l-Boc-amino-3-cyclopentene (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL)/water (7.8 mL) (8: 1) at room temperature was added N-methyl morpholine N-oxide (2.48 g, 21.16 mmol). After 2 minutes osmium tetroxide (4% in water) (3.37 mL) was added and the resulting mixture stirred at room temperature for 23h. The reaction mixture was then quenched by the addition of aqueous Na2S203 (0.2 M, 25 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with aqueous Na2S203 (0.2 M, 10 mL), dried (MgS04), filtered and evaporated in vacuo. The crude material was purified by flash chromatography eluting with EtOAc (17 – 100 %) in heptane to give a mixture of the title compounds as a yellow solid (1.31g, 57 %).

According to the analysis of related databases, 193751-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 57561-39-4, These common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, 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. Synthesis of ethyl {2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}acetate A solution of ethyl 2-diazoacetate (0.900 mL, 8.56 mmol), tert-butyl (2-hydroxyethyl)(methyl)carbamate (1.50 g, 8.56 mmol) and rhodium(II) acetate dimer (0.380 g, 0.856 mmol) in CH2Cl2 (10.0 mL) were used to carry out the reaction. After the reaction was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-10% ethyl acetate in n-hexane) to give ethyl {2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}acetate (0.690 g, 31%). 1H NMR (CDCl3, 300 MHz) delta 4.28-4.18 (m, 2H), 4.07 (br s, 2H), 3.65 (br s, 2H), 3.42 (br s, 2H), 2.93-2.92 (m, 3H), 1.45-1.44 (m, 9H), 1.25 (br t, 3H).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National Health Research Institutes; Ueng, Shau-Hua; Yeh, Shiu-Hwa; Lin, Shu-Yu; Shih, Chuan; (329 pag.)US2017/253569; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 37045-73-1, 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. 37045-73-1, name is 3-(Methylsulfonamido)aniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Chloro-6,7-dimethoxy-quinazoline (100 mg, 0.4500 mmol) and 1H-indazol-6-amine (59.27 mg, 0.4500 mmol) were mixed in MeCN (2 mL) and irradiated in a CEM microwave at 100 C for one hour. The reaction mixture was allowed to cool and then passed through a short pad of silica. After concentration of the filtrate, the resultant solid was washed sequentially with acetonitrile and diethyl ether and dried in vacuo to give 16 (0.13g, 81%) as a light brown solid. 1H NMR (DMSO-d6) delta 13.21 (br s, 1H), 11.37 (s, 1H), 8.84 (s, 1H), 8.30 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.41 (d, J=8.6 Hz, 1H), 7.34 (s, 1H), 4.03 (s, 3H), 4.01 (s, 3H)

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, 3-(Methylsulfonamido)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jordan, Allan M.; Begum, Habiba; Fairweather, Emma; Fritzl, Samantha; Goldberg, Kristin; Hopkins, Gemma V.; Hamilton, Niall M.; Lyons, Amanda J.; March, H. Nikki; Newton, Rebecca; Small, Helen F.; Vishwanath, Swamy; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2724 – 2729;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121492-06-6, 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 121492-06-6 as follows.

202cU.l-dimethylethyl (2-{r8-(2,6-difluorophenylV4-r2-niethyl-S-(rr2- phenylethvPaminol carbonyllphenviy7-oxo-7,8-dihydrorhoyrido[23-cf1pyrimidin-2- yli amino } ethypmethylcarbamateTo the solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfmyi)-7-oxo-7,8- dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-(2-phenylethyl)benzainide (156 mg, 0.28 mmol) in dichloromethane (11 mL) was added 1,1-dimethylethyl (2- aminoethyl)methylcarbamate (75 muL, 0.42 mmol) and triethylamine (78.7 muL, 0.56 mmol). The reaction mixture was stirred at room temperature for 16 hours then applied to the flash chromatograph to afford the titled compound 147 mg (79 %). LC-MS m/z 669 (M + H)+; 1H-NMR (MeOD) 1.30 (m, 9 H), 2.31 (m, 3H), 2.65 (m, 2 H), 2.76 (m, 1 H), 2.92 (m, 2 H), 3.22 (m, 2 H), 3.45 (m, 1 H), 3.60 (m, 2 H), 6.35 (m, 1 H), 7.19 (m, 2 H), 7.26 (m, 5 H), 7.43 (m, 1 H), 7.49 (m, 1 H), 7.60 (m, 1 H), 7.74 (m, 1 H), 7.97 (m, 1 H).

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/104915; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics