Tag: M.W=200-300

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. 24451-15-8, name is Ethyl 2-((4-bromophenyl)amino)-2-oxoacetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H10BrNO3

General procedure: A methanolic solution of TBAOH (1.0 M, 2.4 mmol) was addeddirectly to a one-neck round flask suspension of the correspondingN-substituted oxamate proligand (0.6 mmol) in 10 mL of acetonitrileat 60 C. Then, an aqueous solution of K2[PdCl4] (100 mg,0.3 mmol in 5 mL of water) was added dropwise to the reactionmixture and resulting basic solution was heated at 60 C for 10 hunder continuous stirring. The solution was allowed to evaporateat room temperature. X-ray quality yellow prisms were grownup after two weeks (2) and a couple of days (3 and 4). Their formulaswere determined by X-ray diffraction on single crystals.2: Yield: 90%

The synthetic route of 24451-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fortea-Perez, Francisco Ramon; Neve, Francesco; Armentano, Donatella; De Munno, Giovanni; Stiriba, Salah-Eddine; Julve, Miguel; Inorganica Chimica Acta; vol. 443; (2016); p. 267 – 273;,
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Application of 190900-21-1, These common heterocyclic compound, 190900-21-1, name is tert-Butyl 5-oxo-1,4-diazepane-1-carboxylate, 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.

(1171) [00391] To a mixture of 2-(4-bromophenyl)ethanamine (10.0 g, 50.0 mmol) and saturated aqueous sodium bicarbonate (375 ml) was slowly added Cbz-Cl (10.3 g, 8.56 ml, 60.0 mmol). The reaction mixture was allowed to stir at RT for 1 hour (a white precipitate forms) and then extracted with EtOAc (2 x 200 mL). The organic layers were combined, washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by FCC eluting with 5 – 20% EtOAc in hexanes to afford benzyl (4-bromophenethyi)earbamate as a white solid (16.7g, 100%). LCMS (ESI, m/z): 334, 336 [M ] [J .

The synthetic route of 190900-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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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 22808-73-7 as follows. name: Methyl 4-sulfamoylbenzoate

4-Hvdroxymethyl-benzenesulfonamide; To a solution of 5.2 g 4-sulfamoyl-benzoic acid methyl ester in 100 ml. THF and 1.44 ml. MeOH, 0.77 g lithium borohydride was added portion-wise over a period of 10 minutes. The mixture was heated at reflux overnight, cooled to room temperature, and poured onto ice containig 100 ml. 1 N HCI. The mixture was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by automated flash chromatography (EtOAc/Hexane 1 :1 ) to give 0.75 gram (17%) of product. 1H NMR (400 MHz, DMSO-de) delta 4.57 (d, J=5.81 Hz, 1 H), 5.38 (t, J=5.81 Hz, 1 H), 7.48 (d, J=8.34 Hz, 2H), 7.78 (d, J=8.34 Hz, 2H).

According to the analysis of related databases, 22808-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY PHARMACEUTICALS B.V.; WO2009/115515; (2009); A1;,
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24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, 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: 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

6-bromo-3,4-dihydro-2H-benzo[6] [l,4]oxazine (2): To a stirred solution of 6- bromo-2H-benzo[6][l,4]oxazin-3(4H)-one (7 g, 30.8 mmol) in THF (20 mL) was added 1M borane in THF (15.41 mL) at 0 C and stirred for 3 h at reflux temperature. After completion of the reaction, methanol (2 mL) was added to the reaction mixture at 0 C and stirred for 2 h at reflux. After completion of the reaction, cone. HC1 (2 mL) was added to reaction mixture at 0 C and again stirred for 2 h at reflux. The reaction mixture was then neutralized with 2N NaOH solution at 0 C and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography (100-200 mesh silica gel, 15% ethyl acetate in pet. ether as eluent) to afford 2 (3.2 g, 49% yield) as a brown solid. MS m/z (M+H): 214.4

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

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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Reference of 146651-75-4, The chemical industry reduces the impact on the environment during synthesis 146651-75-4, name is tert-Butyl (2-aminophenyl)carbamate, I believe this compound will play a more active role in future production and life.

Example 6; Ethyl l-methyl-8-(2-(^-butoxycarbonylaminophenylamino)-4,5-dihydro-lH- pyrazolo[4,3-h]quinazoline-3-carboxylate (A12BlC2Z); Palladium acetate [Pd(OAc)2] (101 mg, 0.45 mmol), (+)-BINAP (280 mg, 0.45 mmol) and dimethylformamide (65 niL) were charged to a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 minutes and added to a mixture of 2-(t- butoxycarbonylamino)aniline (2.6 g, 12.5 mmol), ethyl 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo[4,3-h]quinazoline-3-carboxylate (1.6 g, 4.16 mmol), and potassium carbonate (5.74 g, 41.6 mmol) in dimethylformamide (50 mL). The resulting mixture was stirred at 700C for 6 hours under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was concentrated, the crude solid was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate 60/40) to afford 1.18 g (61% yield) of the title compound. 1H NMR (400 MHz, DMSO- d6) delta ppm 1.32 (t, J=I lambda Hz, 3 H) 1.46 (s, 9 H) 2.84 (m, 4 H) 2.96 (m, 2 H) 4.20 (s, 3 H) 4.30 (q, J= 7.1 Hz, 2 H) 7.12 (m, 2 H) 7.51 (m, 1 H) 7.71 (m, 1 H) 8.38 (s, 1 H) 8.65 (s, 1 H) 8.60 (s, 1 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, tert-Butyl (2-aminophenyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/74788; (2008); A1;,
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Application of 1012884-46-6, 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. 1012884-46-6, name is 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of magnesium(19.5 grams) and iodine(0.8 grams) in 1000 ml of methanol was added 40 grams of 1 l-chloro-2,3-dihydro-2-methyl-lH-dibenz[2,3:6,7] oxepino [4,5-c] pyrrol- 1 -one at 25-30C and stirred the reaction mixture for 30 minutes at 25-30C. Heated the reaction mixture to reflux temperature and stirred for 1 hr at reflux. After completion of the reaction, the reaction mixture was cooled to 25-30C and water (400 ml) was added. Adjusted the pH of the reaction mixture to 6.4 by using 20 % dil. HC1 at 10-15C. Ethyl acetate (600 ml) was added to the reaction mixture and stirred for 30 minutes. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with 10% NaCl solution. Distilled off the solvent completely under reduced pressure. Isopropyl alcohol (120 ml) was added to the obtained residue. The reaction mixture was cooled to 0-5C and stirred for 2 hrs. Filtered the obtained solid, washed with isopropyl alcohol and dried to get the title compound. Yield: 21 grams.

The synthetic route of 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHU, Elevathingal Nicholas; SATYANARAYANA, Komati; SEETHA RAMA SARMA, Peri; WO2012/38975; (2012); A2;,
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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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide, A new synthetic method of this compound is introduced below., SDS of cas: 22227-26-5

Charged 3,5-bis(trifluoromethyl)benzonitrile (100 gm, 1 meq.), 2 (N) Sodium hydroxide (21.7 gm, 1.3 meq.) into 400 ml methanol and stirred the reaction mass at 20 – 30¡ãC for 2-3 hrs. Added Dimethyl sulphoxide (100 ml) followed by dilute 30percent H202 solution (100 gm diluted in 300m1 water, 2.1 eq.) at 20 -35¡ãC. Stirred the mass for 2-3 hrs. at 20-30¡ãC and confirmed reaction completion by HPLC. Reaction mass quenched by addition of water (500 ml, S Vol). Filtered the slurry and washed the wet cake by water (500 ml, SVol). Dried under vacuum at 50-60¡ãC to get 100 gm 3, 5-bis (trifluoromethyl) benzamide (Purity 99 percent). Charged 3, 5-bis (trifluoromethyl) benzamide, prepared according to procedures a or b, as described above, (100 gm, 1 meq) into N, N Dimethyl formamide (100 ml, 1 vol). Added N, N Dimethyl formamide dimethyl acetal (70 gm, 1.5 meq) at 20-30¡ãC and stirred the reaction mass for 2-3 hrs. Reaction completion for the formation N-((dimethylamino)methylene)-3,5- bis(trifluoromethyl)benzamide was confirmed by HPLC. Cooled reaction mass to 10-15¡ãC and added acetic acid (S00 ml, S vol.) followed by hydrazine hydrate (31 gm, 1.5 meq). Reaction mass was heated to S0-SS¡ãC and stirred for 2-3 hrs. at same temparature. Reaction was monitored by HPLC. Cooled reaction mass to 20-30¡ãC and quenched by addition of water (2.S L, 2S vol.). Filtered the slurry and washed the wet cake by water (S00 ml, S vol.). Dried under vacuum at 50-60¡ãC to get 3 -(3,5 -bis(trifluoromethyl)phenyl)- 1 H-i ,2,4-triazole (94 gr, Purity 97percent).

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:
Patent; WATSON LABORATORIES INC.; MUTHUSAMY, Anantha Rajmohan; KANNIAH, Sundara Lakshmi; RAVI, Akash; DAS, Tonmoy Chitta; CHEMATE, Rajendra Popat; SINGH, Anil Kumar; WAGH, Yogesh Dhananjay; (60 pag.)WO2018/129227; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 406233-31-6, name is 4-Fluoro-3-nitrobenzenesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 406233-31-6, Quality Control of 4-Fluoro-3-nitrobenzenesulfonamide

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-nitrobenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 32428-71-0, name is 2-Chloro-N-(2-ethyl-6-methylphenyl)acetamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32428-71-0, Formula: C11H14ClNO

A. 1-[(2-Ethyl-6-methylphenyl)carbamoylmethyl]-2-methyl-2-imidazoline. In a manner similar to Ex. IA react 21.17 gm. (0.1 M) of 2-chloro-2′-ethyl-6′-methylacetanilide and 42.1 gm. (0.5 M) of lysidine in 250 ml. of nitromethane, to obtain the title compound: NMR (CDCl3): delta=1.16(t,3), 1.97(s,3), 2.18(s,3), 2.54 (q,2), 3.10-3.70(m,4), 3.87(s,2), 7.15 (s,3) and 8.78(bs,1)ppm.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Berlex Laboratories, Inc.; US4353921; (1982); A;,
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Reference of 579474-47-8, These common heterocyclic compound, 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, 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.

A solution of 0110-31 (200 mg, 0.4 mmol), TBTU (200 mg, 0.6 mmol), N1, Lambdaf2-diisopropylethane-l, 2-diamine (364 mg, 2.82 mmol), and tert-butyl 2-amino-4- fluorophenylcarbamate (0113-60) (90 mg, 0.4 mmol) in DMF (4 mL) and THF (2 mL) was stirred at r.t. for 3 hours. Then DMF and THF were removed under reduced pressure and the residue was dispensed in water and filtered to get the crude product. The crude compound was further purified by flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford pure product tert-butyl 2-(4- (4-(2-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-ylamino)-2- oxoethyl)phenoxy)butanamido)-4-fluorophenylcarbamate (150 mg, 54%) as a pale yellow solid. LCMS : 698 [M+ 1 ]+.

Statistics shows that tert-Butyl 2-amino-4-fluorophenylcarbamate is playing an increasingly important role. we look forward to future research findings about 579474-47-8.

Reference:
Patent; CURIS, INC.; QIAN, Changgeng; CAI, Xiong; ZHAI, Haixiao; WO2010/75542; (2010); A1;,
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