Author: Jessica.F

25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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. Application In Synthesis of 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide

Sodium hydride in mineral oil (21.40 mg, 0.535 mmol) was added to a, stirring, ice-bath cooled solution of 3-[4-(4,5-dimethyl-1 H-imidazol-1 -yl)phenyl]-1 , 4-diazaspiro[4.4]non-3- en-2-one (D28) (150 mg, 0.486 mmol) in DMF (5 ml) under argon. After stirring for 30 min. a solution of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (137 mg) in DMF (3 ml) was added over 1 h using a syringe pump maintaining an ice-bath temperature. The resulting reaction mixture was allowed to come to room temperature then stirred for a further 4 h. The reation mixture was diluted with methanol (20 ml) and applied to an SCX column (1Og). After washing with MeOH (50 ml) the product was eluted with 2M NH3-MeOH. Evaporation of the solvent afforded a brown gum. On dissolving in 1 :1MeOH:DMSO for MDAP purification a small amount of white solid precipitated. This was collected, washed with diethyl ether and dried The material was reapplied to an SCX column (1g) in MeOH (10 ml), washing (30 ml MeOH) and eluting as described above to remove residual DMSO. Drying afforded the free-base of the title compound as a white solid (20 mg).1H NMR (CDCI3) delta: 1.80 – 2.15 (8H, bm), 2.17 (3H, s, overlapping with adjacent bm), 2.25 (3H, s), 4.30 (2H, s), 7.40 (4H, m), 7.58 (1 H, s), 7.68 (1 H, d), 7.84 (1 H, s), 8.57 (2H, d),9.32 (1 H, s).Mass Spectrum (Electrospray LC/MS): Found 510 (MH+). C27H26F3N5O3 requires 509. Ret. time 1.81 min.A solution of the free-base (20 mg) in DCM (2 ml) was treated with an excess of 1 M HCI in diethyl ether (0.12 ml, 0.120 mmol). The volatiles were removed in vacuo and the residue dried under high vacuum at 550C to afford the title hydrochloride as a pale yellow solid (20 mg).Mass Spectrum (Electrospray LC/MS): Found 510 (MH+). C27H26F3N5O3 requires 509. Ret. time 1.77 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-N-methoxy-N-methylbenzamide

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give the title compound.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
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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. Product Details of 6292-59-7

A solution of compound 13 (2.0 g, 4.36 mmol) and commercially available4-tert-butylbenzenesulfoamide (1.0 g, 4.79 mmol) in toluene (30 mL) was treated withK2CO3 (723 mg, 5.23 mmol) and tetra-n-butylammonium bromide (142 mg,0.44 mmol). The reaction mixture was warmed at 100 C for 18 h and cooled downto ambient temperature. The resulting mixture was filtered through a pad of Celite,and the filtrate was diluted with EtOAc (100 mL); washed with aqueous 1N HCl,water, and brine; dried over anhydrous MgSO4; and concentrated under reducedpressure to provide the crude product. Flash chromatography (SiO2, 3percent MeOH?CH2Cl2) to provide 14 as a green foam (1.75 g, 63percent)

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

Reference:
Article; Lee, Chung Ryul; Lee, Sang Yeul; Nam, Tae-Gyu; Synthetic Communications; vol. 44; 17; (2014); p. 2488 – 2493;,
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Synthetic Route of 1939-27-1, 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. 1939-27-1 name is N-(3-(Trifluoromethyl)phenyl)isobutyramide, 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 3, put a 100ml three-necked bottle with mechanical stirring and thermometer into the ice machine, add 23ml of concentrated sulfuric acid, stir,Addition of 10.75g of iso – butyramide benzotrifluoride until the solid dissolves, keeping the temperature at -5 C, adding 2.3ml of 95% fuming HN03, stirring 3h; Step 4, the above reaction was poured into a certain amount of ice water mixture, was sticky solid, add 80g toluene, stirring,Separation, the upper organic phase was washed three times with 3% sodium bicarbonate solution, followed by three washes, and the solvent was removed by rotary evaporation to give a yellow solid; Step 5, the above yellow solid was added to the flask, 20 ml of ethanol was added, and the mixture was heated to reflux, solid 1% of activated carbon was added, stirred for 5 minutes, and hot filtered.The filtrate was cooled to room temperature, and petroleum ether was slowly added thereto until the solution became turbid. The solution was refrigerated at 0C for 3 hours, filtered, and dried at 60C to obtain flunitamide as a pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(3-(Trifluoromethyl)phenyl)isobutyramide, and friends who are interested can also refer to it.

Reference:
Patent; Xuzhou Nuokefei Pharmaceutical Technology Co., Ltd.; Zhao Qingling; Li Weixin; (7 pag.)CN108003051; (2018); A;,
Amide – Wikipedia,
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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 4815-28-5 as follows. Product Details of 4815-28-5

General procedure: 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide(4a;1.5 mmol) was suspended in 10 ml butanol and benzaldehydes(5a-5m;1.0 mmol). Conc HCl (0.1 ml) was added to this reaction mixture and heated at 80 C for 12 h or until TLC confirms the completion of reaction. The solid obtained was filtered, washedwith water and dried.

According to the analysis of related databases, 4815-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Amawi, Haneen; Karthikeyan, Chandrabose; Pathak, Rekha; Hussein, Noor; Christman, Ryann; Robey, Robert; Ashby, Charles R.; Trivedi, Piyush; Malhotra, Ashim; Tiwari, Amit K.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 1053 – 1065;,
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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 885-70-1 as follows. Recommanded Product: 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one

(a) 5,11-Dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one To a suspension of 7.4 g (0.035 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 150 ml of anhydrous tetrahydrofuran, 44.8 ml (approx. 0.07 mol) of a 15% solution of n-butyl-lithium in n-hexane was added dropwise with stirring at a reaction temperature of from 0 to +10 C. After it had all been added, the mixture was stirred for 30 minutes at ambient temperature before a solution of 4.16 g (0.035 mol) of 3-bromo-prop-1-yne in 25 ml of anhydrous tetrahydrofuran was added dropwise. The resulting mixture was stirred for a further 2 hours at ambient temperature, added to 1 liter of saturated aqueous saline solution and the resulting mixture was extracted exhaustively with ethylacetate. The combined ethylacetate extracts were washed twice more with 100 ml of saturated saline solution, dried over sodium sulphate with the addition of 1 g of activated charcoal and evaporated down in vacuo. The residue was purified on silica gel by chromatography using dichloromethane/ethyl acetate 95/5 (v/v) as eluant. 8.5 g (97% of theory) of colourless crystals were obtained, m.p. 199 C. (decomposition).

According to the analysis of related databases, 885-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Karl Thomae GmbH; US5006522; (1991); A;,
Amide – Wikipedia,
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Reference of 4141-08-6, These common heterocyclic compound, 4141-08-6, name is 2-Amino-N-methylbenzamide, 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.

General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2-3 equiv) and absolute ethanol (2-3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 C for 12-72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5%ether in pentane. The following compounds were prepared:

The synthetic route of 4141-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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Application of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(3) A mixed solution of the compound 4 (150 mg), the compound 5 (11 mg), and sodium carbonate (87 mg) in acetonitrile (5 mL) was stirred for 18 hours at 50C under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, and dried over Chem Elut (registered trademark). The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent: chloroform-methanol; gradient: 100:0-95:5). The resultant residue was suspended and washed in ethyl acetate to give the compound 6 (77 mg) as a yellow solid. MS (APCI) 366 [M+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, N-Isopropyl-2-chloroacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; SAKAKIBARA, Ryo; USHIROGOCHI, Hideki; SASAKI, Wataru; ONDA, Yuichi; YAMAGUCHI, Minami; AKAHOSHI, Fumihiko; (69 pag.)EP3381904; (2018); A1;,
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These common heterocyclic compound, 5466-88-6, name is 2H-1,4-Benzoxazin-3(4H)-one, 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. Recommanded Product: 2H-1,4-Benzoxazin-3(4H)-one

To a stirred solution of 4H-Benzo[1 ,4]oxazin-3-one (2.5 g, 16.77 mmol) in DMF (10 mL) was added potassium tert-butoxide (2.81 g, 25.16 mmol) at 0 C. After stirring for 5 min, methyl iodide (3.54 g, 25.16 mmol) was added and the reaction mixture was stirred for another 3h. The reaction was quenched by addition of water and extracted with ethyl acetate (30 x 2 ml). The organic layer was washed with water (20 mL), and evaporated to get a crude product 2.2 g.

The synthetic route of 2H-1,4-Benzoxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BEBERNITZ, Gregory Raymond; BOCK, Mark G.; BHUNIYA, Debnath; DATRANGE, Laxmikant; KURHADE, Suresh Eknath; PALLE, P. Venkata; REDDY, Dumbala Srinivas; WO2011/48148; (2011); A2;,
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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,
Amide – an overview | ScienceDirect Topics