Tag: M.W=200-300

Synthetic Route of 129686-16-4, 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. 129686-16-4 name is 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, 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.

A solution of 6-bromo-3,4-dihydro-lH-[l,8]naphthyridin-2-one (l .Og, 4.4 mmol), tert- butyl acrylate (2.56 ml, 17.62 mmol) and N,N-diisopropylethylamine (1.46 ml, 8.81 mmol) in acetonitrile (20 ml) and DMF (7 ml) was stirred and degassed with nitrogen gas for 10 minutes. Tri-o-tolylphosphine (0.27 g, 0.88 mmol) and palladium (II) acetate (47% on Pd) (0.099 g, 0.44 mol) were added and the resulting mixture was microwaved (1600 W, 180C, 35 minutes). The reaction mixture was evaporated till dryness, taken up in a mixture of DCM/methanol (8/2) (50 ml), filtered through a short pad of celite and washed with DCM. The organic layer was washed with water, dried over MgS04, filtered and evaporated to dryness. The residue was taken up in cold ethanol (10 ml) and stirred at 5C for 5 minutes, the precipitate was filtered off, washed with cold ethanol (3 ml) and dried under vacuum to yield 950 mg intermediate (1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; GUILLEMONT, Jerome, Emile, Georges; LANCOIS, David, Francis, Alain; MOTTE, Magali, Madeleine, Simone; KOUL, Anil; BALEMANS, Wendy, Mia, Albert; WO2013/21051; (2013); A1;,
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These common heterocyclic compound, 162787-61-3, name is 2-(Methylsulfonamido)benzoic 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. COA of Formula: C8H9NO4S

Thereafter, 40 g of Synthesis Intermediate A, 26 g of salicylamide and 2 mL of DMF (N,N-dimethylformamide) were added to 800 mL of toluene, and 22 g of thionyl chloride was added dropwise at room temperature. This solution was stirred at 85 C. for 2 hours, and 3.9 g of p-toluenesulfonic acid monohydrate was added, followed by stirring at 130 C. for 5 hours. The resulting reaction solution was cooled to 60 C. and after adding 30 mL of triethylamine, cooled to room temperature. To this solution, 300 mL of methanol was added, and the obtained solid was filtered and washed with methanol to obtain 52 g of Synthesis Intermediate B (yield: 88%).

The synthetic route of 2-(Methylsulfonamido)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM CORPORATION; US2012/53343; (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. 159184-15-3, name is tert-Butyl 2-(4-aminophenoxy)ethylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 2-(4-aminophenoxy)ethylcarbamate

Step F. tert-Butyl 2-{4-[(1-benzyl-4-piperidinyl)amino]phenoxy}ethylcarbamate tert-Butyl 2-(4-aminophenoxy)ethylcarbamate (2.34 g, 9.27 mmol) and benzyl piperidone (2.6 g, 13.74 mmol) were dissolved in dichloroethane (40 mL). Anhydrous sodium sulfate (13.2 g) was added followed by acetic acid (2.6 mL). Stirring was continued for 1 hour. Sodium triacetoxyborohydride (3.93 g, 18.54 mmol) was added and stirring continued overnight. The mixture was filtered, diluted with dichloromethane (600 mL), and washed with 40percent sodium hydroxide, water and brine. The organic phase was dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 chloroform-methanol). The solvent was removed in vacuo and the resulting oil triturated with hexane to furnish the title compound (2.4 g, 5.64 mmol). MS ((+)ESI, m/z): 426 [M+H]+

According to the analysis of related databases, 159184-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US2002/28832; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature 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.

2.6. Tamsulosin; I IV yield 50% 11 220 g (0.88 mol) of intermediate IV and 84 g (0.79 mol) of sodium carbonate and N, N- dimethylformamide (1500 ml) are added to 208 g (0.85 mol) of intermediate I. The reaction mixture is stirred at 70 C for 5 hours. Water is added to the reaction mixture and product II is extracted with ethylacetate. The evaporation residue is stirred in ethanol and after sucking off, the yield is 173.9 g (50 %) of crude base II. The method according to CZ 291802. The yield is, for comparison, also calculated on the crude base. The reaction takes place at 60 to 70 C for 5 hours and the product is not purified with the demanding column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, its application will become more common.

Reference:
Patent; ZENTIVA, A.S.; WO2005/75415; (2005); A1;,
Amide – Wikipedia,
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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. 672-58-2, name is 3-(Trifluoromethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H6F3NO2S

General procedure: To a stirred solution of glucal (1 equiv.) and N-nucleophile (1.1 equiv.) inanhydrous 1,2-dichloroethanne (2 mL/mmol) under an atmosphere of argon was added Zn(OTf)2 (10 mol%) at 40?C. The reaction mixture was stirred untilthe complete consumption of the starting material (glycal). The solvent wasfiltered and concentrated in vacuo, and the crude residue was redissolved indichloromethane and loaded on a silica gel column. The product was purified by silica gel column chromatography using hexane/EtOAc as the eluent to affordthe 2,3-unsaturated N-glycosides. All of the products were confirmed by1H NMR, 13C NMR, and MS/HRMS spectroscopy and compared with that of literature data; characterization data of new products are outlined in the experimentalsection

According to the analysis of related databases, 672-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddy, Thurpu Raghavender; Battina, Suresh Kumar; Kashyap, Sudhir; Journal of Carbohydrate Chemistry; vol. 34; 3; (2015); p. 133 – 144;,
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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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO2

A mixture of 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (197 mg, 0.864 mmol), (S)-3-phenylmorpholine (172.7 mg, 1.058 mmol), 2-(dicylclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl (11.2 mg, 0.028 mmol), tris(dibenzylideneacetone)dipalladium (0) (8.9 mg, 0.01 mmol), tetrahydrofuran (3.3 mL) and lithium bis(trimethylsilyl)amide in tetrahydrofuran (1 M, 1.93 mL, 2 mmol) was stirred at 70 C. overnight. The mixture was cooled to room temperature and saturated aqueous ammonium chloride and ethyl acetate were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (3*). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (gradient: 0-25% ethyl acetate in heptanes) to afford the title compound (105.6 mg, 39.4%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.01(1H, ddd, J=12.2, 9.3, 4.3 Hz), 3.29 (1H, m), 3.54 (1H, dd, J=11.4, 8.9 Hz), 3.92 (3H, m), 4.15 (1H, m), 4.48 (2H, s), 5.28 (1H, s), 6.37 (1H, d, J=2.5 Hz), 6.56 (1H, m), 6.72 (1 H, d, J=8.8 Hz), 7.16 (3H, m), 7.26 (1H, m), 7.24 (2H, s), 7.97 (1H, s).

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2011/281854; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, molecular formula is C13H19NO3, 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: C13H19NO3

3) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-phenylpiperidine 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 then stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the 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 6.72 g (21.07 mM) of crude product as light-brown solid. To a solution of 6.72 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 ml (42.33 mM) of triethylamine as well as 3.40 g (21.09 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 magnesium sulfate. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow solid. Yield 5.77 g (72%) m.p. 73-74 C. 1H-NMR (200 MHz, CDCl3) delta: 1.46 (9H, s), 1.73-1.88 (4H, m), 1.99-2.19 (1H, m), 2.94-3.08 (2H, m), 3.54 (2H, s), 4.31 (2H, d, J=5.8 Hz), 4.73-4.96 (1H, m), 7.13-7.36 (4H, m). IR (KBr): 3389, 1690, 1518, 1269, 1171 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123986-64-1, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
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 956434-30-3 as follows. Application In Synthesis of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) To a solution of the compound (0.500 g) obtained in Example 29, step 1 and iron(III) acetylacetonate (0.0620 g) in a mixture of THF (10 mL) and 1-methylpyrrolidinone (1 mL) was added 1M isopropylmagnesium chloride ether solution (8.78 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 1N hydrochloric acid, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5?100% ethyl acetate/hexane) to give tert-butyl 8-isopropyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.136 g, 27%) as an oil. 1H-NMR(CDCl3): delta 1.27(6H,d,J=7.0Hz), 1.42(9H,s), 2.93-3.02(1H,m), 3.82-3.84(2H,m), 4.22(2H,brs), 4.35-4.50(2H,m), 6.88(1H,d,J=7.5Hz), 7.40-7.60(1H,m) MS(ESI+):293(M+H)

According to the analysis of related databases, 956434-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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. Quality Control of 4-(tert-Butyl)benzenesulfonamide

General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 molpercent) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 ¡ãC for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields.

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

Reference:
Article; Zhao, Zijian; Lian, Yan; Zhao, Chang; Wang, Bing; Synthetic Communications; vol. 48; 12; (2018); p. 1436 – 1442;,
Amide – Wikipedia,
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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. 103500-22-7, name is Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H15NO3

Dissolve the previous product 1-4 (838.5mg, 4mmol) in 50ml of tetrahydrofuran,Cbz-1-aminocyclopropanemethanol (885 mg, 4 mmol) was added, triphenylphosphine (1.31 g, 5.0 mmol) was added, and diethyl azodicarboxylate (DEAD) (970.7 mg, 5.0 mmol) was added,The reaction was stirred at room temperature overnight, filtered, the filtrate was extracted with ethyl acetate, washed with water, and purified by column chromatography to obtain 500 mg of white solid product (1-6), MS: 413, yield: 30.3%.

According to the analysis of related databases, 103500-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Li Haibo; Lv Haibin; Li Xinghai; Chen Yuanwei; (14 pag.)CN110551065; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics