Author: Jessica.F

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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C10H15NO2S

Example 3Preparation of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt using Acetone as a solvent and potassium hydroxide as a base; Acetone (45.0 ml), Potassium hydroxide (1.13 gm) and 4-tert-butylbenzenesulphonamide (1.65 gm) were added at 30 C. and stirred for 5 minutes. 4,6-dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine (3.0 gm) was added at 30 C. and the temperature of the reaction mass was raised to reflux. The reaction mass was stirred at reflux for 6.5 hrs. The reaction mass was cooled gradually to room temperature. Acetone was distilled out from the reaction mass under vacuum below 40 C. Water (30.0 ml) was added to the reaction mass at room temperature and the resulting mass was stirred for 3.0 hrs. The precipitated solid was filtered, washed with water (2¡Á3.0 ml) and dried under vacuum at 55-60 C. for 6.0 hrs to obtain 4.04 gms of 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzene sulfonamide potassium salt. (% Yield: 89%)MS of solid: 564.1 (M+H), 548.1, 514.2, 434.1, 370.0, 352.1, 340.0, 324.1, 249.2, 237.1, 197.6, 182.9

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANDOZ AG; US2012/136015; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 3984-14-3, name is N,N-Dimethylsulfamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1?-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) ? ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below. 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). were added to a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, and the mixture was placed under N2. After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 C. for 2 h. After cooling to 30 C., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered, and then concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 C., and heptane (2 L) was then added slowly. The resulting mixture was stirred and cooled to 0 C. It was then filtered. The filter cake was rinsed with a small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) ? 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/275930; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 4793-24-2,Some common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, molecular formula is C7H5ClFNO4S, 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-chloro-4-fluoro-5-sulfamoylbenzoic acid (3.2 g, 12.65 mmol) in THF (10 mL) was added 1M BH3 THF (38 mL, 38.0 mmol). After stirring 12h, the reaction mixture was quenched with MeOH and concentrated in vacuo. The residue was purified by chromatography (silica, EtO Ac-Hex) to afford 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.9 g). To a suspension of 4-chloro-2-fluoro-5- (hydroxymethyl)benzenesulfonamide (1.78 g, 7.43 mmol) in DCM (10 mL) was added PBr3 (2.2 lg, 8.17 mmol). The reaction was stirred for 24 h when it was determined to be complete by GCMS. The reaction was carefully quenched with H20 and then partitioned between THF and brine. The organic layer was dried over Na2S04 and concentrated in vacuo to afford 5-(bromomethyl)-4-chloro-2-fluorobenzenesulfonamide (1.98 g) as an off-white solid. 1H-NMR (DMSO-d6, 400 MHz) delta 8.08 (d, J = 7.8 Hz, 1H), 7.84 (s, 2H), 7.80 (d, J = 9.9 Hz, 1H), 4.83 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WO2011/71565; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-methoxy-5-sulfamoylbenzoate

(4) Add 245 g (1.0 mol) of methyl 2-methoxy-5-sulfamoylbenzoate prepared in step (3) and 2772 g of 5% sodium hydroxide solution by weight to the reactor, Stir the reaction for 20 h, and the reaction temperature does not exceed 40 . After the reaction, adjust the pH to 1 with 5% by weight of dilute hydrochloric acid and filter. The resulting filter cake is washed with water, dried, and recrystallized from methanol to produce 209.06 g of 2-methoxy-5-sulfamoylbenzoic acid, yield 90.5%.

According to the analysis of related databases, 33045-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suzhou Chenghe Pharmaceutical And Chemical Co., Ltd.; Chen Xiaoqiang; Fang Huan; (7 pag.)CN111100042; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6292-59-7

General procedure: A Schlenk tube with a magnetic stir bar was charged with [RhCp*Cl2]2 (7.8 mg, 12.5 mumol), AgSbF6 (17.2 mg, 50 mumol), PhI(OAc)2 (120.4 mg, 0.375 mmol), NaOAc (6.2mg, 75 mumol), 8-methylquinoline derivative 1 (0.50 mmol), amide 2 (0.25 mmol), and DCM (1.0 mL) under an N2 atmosphere. The resulting mixture was stirred at room temperature for 48 h and then diluted with 3 mL of dichloromethane. The solution was filtered through a celite pad and washed with 10-20 mL of dichloromethane. The filtrate was concentrated and the residue was purified by column chromatography on silica gel to provide the desired product.

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Xiaolei; You, Jingsong; Chemistry Letters; vol. 44; 12; (2015); p. 1685 – 1687;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 125414-41-7, The chemical industry reduces the impact on the environment during synthesis 125414-41-7, name is tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate, I believe this compound will play a more active role in future production and life.

2.97 g of lipoic acid (LA), 3.31 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC¡¤HCl) was added to a 100 mL round bottom flask.Add 40 mL CH2Cl2 to dissolve and activate for 30 min.1.25 g of Boc-serinol dissolved in 20 mL of CH 2 Cl 2 and 2.21 g of 4-(dimethylamino)pyridine (DMAP) were added to the above mixture.Reaction for 12 h. After the reaction is completed, it is filtered.The filtrate was thoroughly washed with an excess of 0.1 mol/L hydrochloric acid.Discard the water phase after standing. Dry the oil phase with sodium sulfate and purify by column chromatography (eluent: CHCl3/CH3OH=20/1, v/v) to give a pale yellowOily liquid di-Boc-LA-Ser (3.19 g, yield 86%).Take 1g di-Boc-LA-Ser in 10mL CH2Cl2,After cooling to 0 C, 0.41 g of trifluoroacetic acid (TFA) was slowly added dropwise and reacted for 2 h.The mixture was concentrated in vacuo to give a crude di-L-Ser.

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 (1,3-dihydroxypropan-2-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southeast University; Li Xinsong; Ling Longbing; He Wei; (21 pag.)CN109224082; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 28460-30-2,Some common heterocyclic compound, 28460-30-2, name is 2,4,6-Trichlorobenzenesulfonamide, molecular formula is C6H4Cl3NO2S, 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: To a solution of 500 mg of 6-(4-amino-phenyl)-1H-pyrazolo[3,4-b]pyrazin-3-ylamine hydrochloride and 397 mg of 2-fluoro-5-methyl-benzenesulfonyl chloride in 4 ml DCM, 0.16 ml pyridine were added and the reaction mixture was stirred for 16 h at RT. Then, the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc. The fractions containing the product were combined and the solvent evaporated under reduced pressure. The title compound was prepared by adapting the procedures described in example 19, employing 2,4,6-trichlorobenzenesulfonamide instead of 2-fluoro-5-methyl-benzenesulfonyl chloride. MS (ES+): m/e = 470.1 (M+H), chloro pattern.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trichlorobenzenesulfonamide, its application will become more common.

Reference:
Patent; SANOFI; Nazare, Marc; Halland, Nis; Schmidt, Friedemann; Weiss, Thilo; Hofmeister, Armin; EP2570415; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1746-77-6, name is Isopropyl carbamate, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

EXAMPLE 113 4-[[[3-[(aminoiminomethyl)amino]phenyl]carbonyl]amino]-2-methoxy-N-[(1-methylethoxy)carbonyl]phenylalanine, trifluoroacetate salt, monohydrate STR330 Steps A/B/C STR331 The above compound was prepared from methyl pyruvate, isopropylcarbamate and 2-bromo-5-nitro anisole using the procedures described in Example 76 Steps A, B and C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1746-77-6.

Reference:
Patent; G. D. Searle & Co.; US5952381; (1999); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 96-30-0, 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 96-30-0 as follows.

In a sealed tube, intermediate 77 (287.19 mg, 2.67 mmol) was added to a solution of 6-chloro-4-nitroindole (350.00 mg, 1.78 mmol) and Cs2CO3 (870.11 mg, 2.67 mmol) in dryDMF (3.5 mL) under N2. The mixture was stirred at 90 C for 17 h. The reaction mixturewas diluted with EtOAc and water and the layers were separated. The organic layer waswashed with brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give 378 mg of intermediate 67 (79% yield, brown solid) which was directly engaged in the next step without further purification.

According to the analysis of related databases, 96-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)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: 1103234-56-5

Step A: Diphenylphosphonic azide (9.082 mL, 0.04214 mol) was added to stirred solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (10.234 g, 0.036647 mol) and triethylamine (11.75 mL, 0.08429 mol) in tetrahydrofuran (100 mL, 1 mol) and the reaction mixture was stirred at room temperature for 3 hours and then heated to reflux for an additional hour. lH-pyrazole (2.5 g, 0.037 mol) was added to the reaction mixture, followed by heating to reflux for 1 additional hour. After cooling to room temperature and removal of the solvent under reduced pressure, an orange-colored oil was obtained. This crude material was purified by silica gel chromatography; eluent: 0-50% ethyl acetate: heptane. The obtained material was recrystalized from 150 mL of a solution of ethyl acetate / heptane (1:3, v/v) to give N-(2,6- difluoro-3-(propylsulfonamido)phenyl)-lH-pyrazole-l-carboxamide with 90% purity (4.4 g, 87%). 1H NMR (500 MHz, DMSO-d6) delta 10.33 (s, IH), 9.70 (s, IH), 8.41 (d, J=2.6, IH), 7.92 (d, J=Ll, IH), 7.42 (td, J=8.9, 5.8, IH), 7.22 (t, J=9.2, IH), 6.62 (dd, J=2.7, 1.6, IH), 3.13 – 3.03 (m, 2H), 1.80 – 1.70 (m, 2H), 1.04 – 0.93 (m, 3H). LC/MS: m/z 345.2 [M+l].

The synthetic route of 1103234-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; PULK, Rebecca; RUDOLPH, Joachim; WEN, Zhaoyang; WO2011/25965; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics