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. 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

B) tert-Butyl 4-cyano-4-(4-fluorophenyl)piperidine-1-carboxylate To a mixture of 33.3 g of 60percent sodium hydride in oil in 200 ml of DMSO and 100 ml of THF is added dropwise, at rt, a solution of 50 ml of 4-fluorophenylacetonitrile and 101 g of the compound obtained in the preceding step in 200 ml of THF, and the mixture is stirred for 2 hours at rt and then refluxed for 1 hour and stirred at rt overnight. The reaction mixture is poured into saturated NH4Cl solution, the THF is concentrated under vacuum, the aqueous phase is diluted with water and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The orange oil obtained is taken up in a minimum amount of ether and the crystalline product formed is filtered off by suction. 87.6 g of the expected product are obtained.

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; SANOFI-AVENTIS; US2007/142349; (2007); 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 2886-65-9 as follows. Computed Properties of C15H10ClFN2O

EXAMPLE 5 8-Chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, ethyl ester Potassium t-butoxide, 1.29 g (0.0115 mol) was added to a stirred solution of 2.88 g (0.01 mol) of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-one in 50 ml of tetrahydrofuran, that had been cooled in an ice bath and covered with a nitrogen atmosphere. After stirring for 5 minutes, 2.59 g (0.015 mol) diethyl chlorophosphate was added. After stirring for 5 minutes, a mixture of 2.26 g (0.02 mol) of ethyl isocyanoacetate in 50 ml of tetrahydrofuran that had been treated with 2.24 g (0.02 mol) of potassium t-butoxide just prior to the addition, was added. After 5 minutes, the ice bath was removed and the stirring was continued for 15 minutes. The mixture was acidified with 2 ml of glacial acetic acid, diluted with 200 ml of saturated sodium bicarbonate solution and extracted twice with 125 ml portions of toluene. The extracts were dried and evaporated and the residue was crystallized from ether to give the product with mp 195-197. For analysis, the material was recrystallized from methylene chloride/ether/hexane to give colorless crystals with mp 195-196. Anal. Calcd for C20 H15 ClFN3 O2: C, 62.59; H, 3.94; N, 10.95. Found: C, 62.59; H, 3.73; N, 11.01.

According to the analysis of related databases, 2886-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4118386; (1978); A;,
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Reference of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl (tert-butoxycarbonyl) oxycarbamate (2.71 g, 11.64 mmol) and 1- (bromomethyl) -4-fluorobenzene (2 g, 10.58 mmol) in DCM To the solution was added NaOH (11.64 mL, 11.64 mmol) followed by tetrabutylammonium bromide (3.41 g, 10.58 mmol) and stirred overnight at room temperature. Water (100 mL) was added to the reaction mixture, and the product was extracted with ethyl acetate (3 * 100 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give 5.5 g of crude material. The crude material was purified by Iscor using a 40 g silica gel column and the product was eluted with 10% ethyl acetate in petroleum ether to give tert-butyl (tert-butoxycarbonyl) oxy (4-fluorobenzyl) carbamate (3.1 g, 8.99 mmol, 85% yield) as a colorless sticky material.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beu Lease Tol-mai Ground Wire Seukwp Keompeoni; I Seul-ram-, -i-ma-dul; Tang Ga-ti-ru-pa-ti-, -seu-ri-ni-ba-san; Wa Ri-e-reu-, -ja-ya-ku-ma-reu-san-ka-ra; Che Ru-ku-, -seu-ri-ni-ba-seu; Sye Ti-, -pu-reu-ni-ma; Ma Ko-reu-, -jon-i-.; (44 pag.)KR2018/64507; (2018); A;,
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Synthetic Route of 118684-31-4,Some common heterocyclic compound, 118684-31-4, name is tert-Butyl (3-(hydroxymethyl)phenyl)carbamate, molecular formula is C12H17NO3, 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 the solution of 6 (5g, 22.4mmol) , and TEA (12.54mL, 89.6mmol) in DCM (100mL) was added MsCl (3.47mL, 44.8mmol) in DCM (20mL) dropwise over 20 min at -15 under nitrogen atmosphere. The resulting mixture was warmed to 0, and stir for 16h. The reaction mixture was poured into 100mL water, and stir for 5min. Collected the organic phase, concentrated in vacuo, and purified by column chromatography to give desired protuct 7 (1.86g, 27.6%) .

The synthetic route of 118684-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); A1;,
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Synthetic Route of 89979-12-4, These common heterocyclic compound, 89979-12-4, name is 5-Chloro-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.

General procedure: To a solution of 5-chloro-N,6-dimethyl-2-[(1S)-1-(methylamino)propyl] pyrazolo[1,5-a] pyrimidin-7-amine (97 mg,0.361 mmol) and 5-chloro-2-(methylsulfonamido) benzoic acid(99 mg, 0.397 mmol) in N,N-dimethylformamide (1.0 mL)was added trimethylamine (0.25 mL, 1.80 mmol) and1-[bis(dimethylamino) methylene]-1H-1,2,3-triazolo[4,5-b]-pyridinium 3-oxide hexafluorophosphate (0.17 g, 0.433 mmol).After stirring at room temperature for 1 h, the reaction mixturewas purified by reversed-phase preparative HPLC toobtain 5-chloro-N-{(1S)-1-[5-chloro-6-methyl-7-(methylamino)-pyrazolo[1,5-a] pyrimidin-2-yl] propyl}-2-[(methanesulfonyl)-amino]-N-methylbenzamide (0.13 g, 0.904 mmol, 90%) as acolorless powder

The synthetic route of 89979-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamaguchi-Sasaki, Toru; Tamura, Yunoshin; Ogata, Yuya; Kawaguchi, Takanori; Kurosaka, Jun; Sugaya, Yutaka; Iwakiri, Kanako; Busujima, Tsuyoshi; Takahashi, Ryo; Ueda-Yonemoto, Naoko; Tanigawa, Eiji; Abe-Kumasaka, Tomoko; Sugiyama, Hiroyuki; Kanuma, Kosuke; Chemical and Pharmaceutical Bulletin; vol. 68; 4; (2020); p. 345 – 362;,
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Reference of 201162-53-0, These common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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 tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1 g, 4.71 mmol, 1.00 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), 5-chloropyridin-2-carbonitrile (651 mg, 4.67 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 2 h at 80 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3*20 mL of ether and the organic layers combined. After concentration, the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:2) to afford 1 g (68%) of the title compound as a solid. LCMS (ESI, m/z): 315.17 [M+H]+

Statistics shows that 3-Boc-3,8-Diazabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 201162-53-0.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
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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. 6269-91-6, name is 2-Methyl-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8N2O4S

To a solution of 3-aminosulfonyl-4-methylnitrobenzene in dichloromethane and methanol was added 10percent Pd/C and the mixture shaken under a hydrogen atmosphere at 50 psi for 15 minutes.The mixture was filtered through diatomaceous earth and the filter cake was washed with methanol.The combined organic solvents were concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 3-aminosulfonyl-4-methylaniline, LCMS: purity: 87percent; MS (m/e): 187 (MH+).

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 6269-91-6.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2012/232106; (2012); A1;,
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Application of 6292-59-7, 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 6292-59-7 as follows.

Step-4:Preparation of 4-(14-dimethylethyl)-N-[6-chloro-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4- yl|benzenesulfonamide (VII).5-(2-Methoxyphenoxy)-2-(pyrimidin-2-yl)-tetrahydropyrimidin-4,6-dione (IV) (10Og,320.22mmol) was added to phosphorous oxychloride (196.4g). The resulting reaction mass was slowly heated to 103-1050C and stirred for 4 hrs. The reaction mass was added to a mixture of toluene (450ml) and water (350ml) at 20-500C and treated with 30percent w/w aqueous sodium hydroxide solution (271.5ml) at 70-800C. The organic layer was separated and treated with activated carbon (7g) at 80-900C for 30min, filtered through hyflo and washed with hot toluene (300ml). 4-(l ,l-Dimethylethyl)benzene sulfonamide (VI) (68.3g, 320.2mmol) was added to the filtrate, followed by potassium carbonate (53.03g, 384.27 mmol) and tetrabutylammonium bromide (3.19g, 9.59 mmol) were added, heated to reflux temperature and separated water azeotropically for 2 hrs, the reaction mass was cooled to 20-250C, filtered the solid and dried. Further, the solid was added to DM water and acidified to pH 0.5 to 0.7 with hydrochloric acid. The solid was filtered washed with DM water and dried to yield 144.5g of title product.Chromatographic purity: 97.92percent (by HPLC, by area normalization)

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:
Patent; AUROBINDO PHARMA LIMITED; BRAJESH, Kumar, Sinha; KONDURU, Rajasekhara, Raju; BUDIDET, Shankar, Reddy; VADDI, Pandu, RangaRao; AMINUL, Islam; MEENAKSHISUNDERAM, Sivakumaran; WO2011/24056; (2011); A2;,
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Related Products of 23530-40-7, A common heterocyclic compound, 23530-40-7, name is N-Methyl-2-nitrobenzenesulfonamide, molecular formula is C7H8N2O4S, 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.

2-Trityl-2H-tetrazol-5-ylmethanol (2.00 g, 5.84 mmol), N-methyl-2-nitrobenzenesulfonamide (1.64 g, 7.59 mmol) and triphenylphosphine (1.53 g, 5.84 mmol) were dissolved in a mixed solvent of tetrahydrofuran (30 mL) and toluene (20 mL), then a solution of diethyl azodicarboxylate in toluene (40%, 2.65 mL, 5.84 mmol) was added thereto and the mixture was stirred at room temperature for throughout a night. After the mixture was passed through a silica gel column (eluting solvent: ethyl acetate/hexane = 40/60) to remove original point components, acetone (5 mL) and acetonitrile (25 mL) were added to the residue prepared by concentrating in vacuo. Mercaptoacetic acid (0.73 mL, 11 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (3.1 mL, 21 mmol) were added to the resulting suspension and the mixture was stirred at 60C for 7 hours. The reaction solution was concentrated and the residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated saline solution successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by a silica gel chromatography (eluting solvent: triethylamine/ethyl acetate = 1/99) to prepare N-methyl-N-(2-trityl-2H-tetrazol-5-yl)methylamine (396 mg, 1.11 mmol, yield: 19.0%). 1H NMR (CDCl3) delta(ppm): 2.45 (s, 3H), 4.07 (s, 2H), 7.07-7.36 (m, 15H).

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; KYOWA HAKKO KOGYO CO., LTD.; EP1547616; (2005); 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. 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) A solution of the compound (0.285 g) obtained in Example 29, step 1, phenylboronic acid (0.183 g) and potassium carbonate (0.138 g) in a mixture of toluene (10 mL) and water (0.5 mL) was degassed with argon gas, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.116 g) was added, and the mixture was stirred under argon atmosphere at 90C for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10?33% ethyl acetate/hexane) to give tert-butyl 8-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.040 g, 12%) as a white powder. 1H-NMR(CDCl3): delta 1.43(9H,s), 3.85-3.88(2H,m), 4.26-4.29(2H,m), 4.42-4.58(2H,m), 7.38-7.75(5H,m), 7.98(2H,d,J=7.2Hz)

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 956434-30-3.

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