Tag: M.W=200-300

Reference of 207405-68-3, The chemical industry reduces the impact on the environment during synthesis 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: To the solution of compound 13 (0.11 g, 0.25 mmol) and bicyclicamine (0.38 mmol) in THF (3 mL) was added DIPEA (0.38 mmol). Afterstirred at R.T. for 1 h, the reaction mixture was diluted with EtOAc,washed with brine, dried over MgSO4, and evaporated. The residue waspurified by column chromatography to give the product.4.1.6. tert-butyl (endo)-3-((2,6-dichloro-8-((2-fluoro-4-(methylsulfonyl)phenyl)amino)pyrimido[5,4-d]pyrimidin-4-yl)amino)-8-azabicyclo[3.2.1]octane-8-carboxylate (14a)Yellow solid, 32% yield. 1H NMR (300 MHz, CDCl3) delta (ppm): 9.12(d, J=3.2 Hz, 1H), 8.95 (t, J=8.1 Hz, 1H), 7.80 (m, 2H), 7.45 (d,J=7.7 Hz, 1H), 4.50-4.20 (m, 3H), 3.10 (s, 3H), 2.50-2.10 (m, 4H),2.00-1.80 (m, 4H), 1.50 (s, 9H). HRMS-ESI (m/z) calcd forC25H28Cl2FN7O4S [M+Na]+: 634.1182, found 634.1234

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 endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fang, Yuanying; Xu, Jun; Li, Zhifeng; Yang, Zunhua; Xiong, Lijuan; Jin, Yi; Wang, Qi; Xie, Saisai; Zhu, Wufu; Chang, Sheng; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4080 – 4087;,
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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-(2-Aminoethyl)benzenesulfonamide

To a solution of 1- (3-isocyanatopropyl) -4-methoxybenzene (0.78 mmol) in THFWas added 4- (2-aminoethyl) benzenesulfonamide (0.86 mmol) at room temperature to a solution (20 ml)Was slowly added over 10-15 minutes. The reaction mixture was stirred at 40-45 [deg.] C for 24 hours. The next day TLC confirmed the termination of the reaction. The solvent was distilled off and ammonium chloride (100 & lt; RTI ID = 0.0 & gt;Ml), 1N HCl solution (50 ml) and ethyl acetate (100 ml). The organic layer was washed with brine and then dried with sodium sulfate. The solvent was distilled off and the residue was adsorbed onto silica gel using methylene chloride. The title compound was then purified by column chromatography using ethyl acetate and hexane.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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 42137-88-2 as follows. category: amides-buliding-blocks

N,N-Bis(2-chloroethyl)-p-toluenesulfonamide (171 mg, 0.576 mmol), potassium iodide (191 mg, 1.15 mmol) and K2C03 (159 mg, 1.15 mmol) were added to a stirring solution of N1- (5-chloro-4-(lH-indol-3-yl)pyrimidin-2-yl)bicyclo[3.2.1]octane-l,5-diamine_(195 mg, 0.384 mmol). The resulting mixture was then heated at 130 C for 16h. The solution was cooled to room temperature, diluted with EtOAc (100 mL) and washed with H20 three times (50 mL). The organics were combined, dried over Na2S04, filtered and evaporated to dryness. The mixture was purified by Si02 column (DCM/EtOAc 0 to 60% gradient) and afforded the title compound (133 mg, 0.182 mmol, 47%) as an off white solid.

According to the analysis of related databases, 42137-88-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; SPROTT, Kevin; MARINEAU, Jason, J.; SCHMIDT, Darby; BRADLEY, Michael; CIBLAT, Stephane; SIDDIQUI, M., Arshad; KABRO, Anzhelika; LEBLANC, Melissa; LEGER, Serge; ROY, Stephanie; WINTER, Dana, K.; MILLER, Tom; RIPKA, Amy; LI, Dansu; WO2015/154039; (2015); A2;,
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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

To a scintillation vial charged with the 6-bromo-4H-benzo[1,4]oxazin-3-one, Pd2(dba)3 (2.5 % substrate), 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl (6% substrate). The vial is purged under a positive flow of nitrogen and 1,4-dioxane, the amine and lithium hexamethyldisylazide (1 equivalent substrate) was added via syringe. The reaction is stirred for overnight at 90C under an atmosphere of nitrogen. Upon cooling the reaction is concentrated onto celiteunder reduced pressure and purified via flash column chromatography or by preparative LCMS.

According to the analysis of related databases, 24036-52-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/15259; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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

Example 10a Chiral isomer 12-{3-[4-(4-methyl-1 H-imidazol-1 -yl)phenyl]-2-oxo-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-1 -yl}-N-[3-(trifluoromethyl)phenyl]acetamide hydrochloride 3-[4-(4-Methyl-1 H-imidazol-1 -yl)phenyl]-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D31 a), isomer 1 (94mg) in DMF (6ml) was cooled to ice bath temp and treated with sodium hydride 60% in oil (13mg) under an atmosphere of argon. The mixture was stirred for 20 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (85mg) in DMF (2.5ml) was added over 1.5 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The solvent was partially removed and the residue was purified by low pH MDAP. The fractions were loaded onto SCX and the free base was eluted with 2M methanolic ammonia. The solvent was removed and the residue was dissolved in DCM, treated with HCI-Et2O, solvent removed and a white solid was obtained from ether (78mg).1H NMR (DMSO) delta: 1.75 (2H, m), 2.05-2.35 (obs, m), 2.45 (3H, s), 3.4-3.6 (obs, m), 3.9 (2H, m), 4.98 (2H, m), 7.45 (1 H, m), 7.58 (1 H, m), 7.75 (1 H, m), 7.98 (2H, m), 8.12 (2H, m), 8.58 (2H, m), 9.63 (1 H, s), 10.74 (1 H, s). 19F NMR (DMSO) delta: 61.4 Mass Spectrum (LC/MS): Found 512 (MH+). Ret. time 1.63 min.Example 10b Chiral isomer 2 2-{3-[4-(4-methyl-1 H-imidazol-1 -yl)phenyl]-2-oxo-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en- 1-yl}-N-[3-(trifluoromethyl)phenyl]acetamide-‘J 3-[4-(4-Methyl-1 H-imidazol-1 -yl)phenyl]-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D31 b), isomer 2 (94mg) in DMF (6ml) was cooled to ice bath temp and treated with sodium hydride 60% in oil (12mg) under an atmosphere of argon. The mixture was stirred for 20 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (85mg) in DMF (2.5ml) was added over 1.5 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine and then dried with hydromatrix and the solvent was removed to give the title compound (104mg). 1H NMR (CDCI3) delta: 1.7 (obs, m), 2.0 (2H, m), 2.15-2.4 (2H, m), 3.31 (3H, m), 3.71 (1 H, m), 3.85 (2H, m), 4.05 (1 H, m), 4.45 (2H, m), 7.10 (1 H, s), 7.3-7.5 (4H, m), 7.68 (1 H, m), 7.84 (1 H, m), 7.94 (1 H, m), 8.60 (2H, m), 9.09 (1 H, s). 19F NMR (DMSO) delta: 62.7 Mass Spectrum (LC/MS): Found 512 (MH+). Ret. time 1.62 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,
Amide – an overview | ScienceDirect Topics

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. 195986-74-4, name is 7-Bromo-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione, A new synthetic method of this compound is introduced below., Formula: C9H7BrN2O2

7-bromo-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (11.8 g, 46.2 mmol) was transferred to a round bottom flask. THF (0.57M) was added to the flask to make a slurry. Lithium aluminum hydride in 1M solution of THF (138.8 mmol) was added dropwise. When the addition was completed, the reaction mixture was heated to 63 C. After 19 hours, the reaction mixture was cooled to room temperature and then to 0 C. Water (3 mL) was added to the cooled reaction mixture, and the reaction mixture was stirred for 1 hour. After the 1 hour, 9 mL of 15% NaOH was added and the reaction mixture was stirred for another hour. Water was then added and the resulting precipitate was filtered off. The precipitate was then washed with ethyl acetate several times. The solvent was removed from the filtrate and the filtrate was transferred to a separatory funnel with ethyl acetate. The filtrate was extracted with ethyl acetate (3¡Á). The combined organic extracts were washed with brine (1¡Á), dried with magnesium sulfate, filtered and concentrated to give a yellow solid. Further purification (1% TEA/Ethyl acetate to start, then switched to 20% ammonia (2M solution in methanol)/ethyl acetate, then 100% methylene chloride) yielded the desired product. [0179] 1H NMR (CDCl3, 400 MHz): delta7.2(s,1H); 7.1 (dd, J=4, 8 Hz, 1H); 6.6(d, J=8 Hz, 1H); 3.8 (s, 2H); 3.0 (dt, J=8 Hz, 4H). [0180] Mass Spec: Calculated: 227.10; Found: 226.96 [M+H]+

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; Wyeth; US2004/9970; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 128263-66-1,Some common heterocyclic compound, 128263-66-1, name is N-(4-(Aminomethyl)phenyl)methanesulfonamide hydrochloride, molecular formula is C8H13ClN2O2S, 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.

Example I N-[4-[[2-Hydroxy-3-(3-methylphenoxy)propyl]aminomethyl]phenyl]methanesulfonamide hydrochloride Heat a mixture of N-[4-(aminomethyl)phenyl]methanesulfonamide hydrochloride(15.0 g, 63.4 mmol) and 1,2-epoxy-3-phenoxypropane (10.41 g, 63.4 mmol) in 63.4 mL of 1 N KOH in methanol and 10 mL of water for about 3.5 h. Remove the solvent to afford crystals of the title compound. NMR (DMSO-d6): delta=2.27(s,3), 2.85-3.15(m,2), 3.02 (s,3), 3.93(s,2), 4.14(s,2), 4.23(br s,1), 5.90(br s,1), 6.74(m,3), 7.19(m,1), 7.24(d,2), 7.53(d,2), ca. 9.35 (br s,2) and 9.97(s,1) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(4-(Aminomethyl)phenyl)methanesulfonamide hydrochloride, its application will become more common.

Reference:
Patent; Schering AG; US5051423; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 830-43-3, These common heterocyclic compound, 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, 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: Pyridine (5 mol) was added to a stirred solution of corresponding amine (1.0 mol) in THF (10 v), after 5 minutes, sulfonyl chloride derivative (1.1 mol) was added, stirred at room temperature under argon atmosphere for 16 h. Then the reaction mixture was diluted with water (50 v), extracted with EtOAc (50 v X 2), evaporated the solvent in vacuo, the crude product was purified by column chromatography to afford 8/9(a-c) and 12/13(a-b) (58-86%) as solids. During thesynthesis of N-(4-(3-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenyl)-4-(trifluoromethyl)benzenesulfonamide (13b), isolated 29% of disulphonation product N-(4-(3 N-(4-(3-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-oxopropyl)phenyl)-4-(trifluoromethyl)-N-(4-(trifluoromethyl)phenylsulfonyl)benzenesulfonamide (13c) as white solid.

Statistics shows that 4-(Trifluoromethyl)benzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 830-43-3.

Reference:
Article; Kasturi, Sivaprasad; Surarapu, Sujatha; Uppalanchi, Srinivas; Anireddy, Jaya Shree; Dwivedi, Shubham; Anantaraju, Hasitha Shilpa; Perumal, Yogeeswari; Sigalapalli, Dilep Kumar; Babu, Bathini Nagendra; Ethiraj, Krishna S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 12; (2017); p. 2818 – 2823;,
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. 89979-12-4, name is 5-Chloro-2-(methylsulfonamido)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Chloro-2-(methylsulfonamido)benzoic acid

Mixed 5-chloro-2-(methylsulfonamido)benzoic acid (28mg, 0.109mmol) with HATU (42mg, 0.109mmol) and dissolved in anhydrous DMF (300uL). Stirred for Ihr. Dissolved hydrogenation product in anhydrous DMF (300uL) and added to the reaction. Added TEA (30uL, 0.218mmol).Stirred for 12 hrs. Diluted with acetonitrile and purified with Prep HPLC to give compound 40 (22mg, 32% yield).1H NMR (400MHz, CD3OD): delta 7.49 (m, 3H), 6.26 (m, 1H), 6.08 (m, 1H), 4.78 (m, 1H), 4.57 (m, 2H), 4.14 (m, 2H), 3.47-3.34 (m, 2H), 3.01 (m, 4H), 2.76 (s, 3H), 2.40-2.05 (m, 2H), 1.73- 1.50 (m, 4H). LC/MS (m/z): 519.2 [M+H]+

According to the analysis of related databases, 89979-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 22503-72-6, These common heterocyclic compound, 22503-72-6, name is 7-Chloro-3-methyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, 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 an ice-cooled solution of 2,3-dihydrobenzothiadiazine 1 or 6-13(1.0 mmol) in CH2Cl2 (10 mL) was added dropwise an excess ofMCPBA (739 mg, 3.0 mmol, 70%) in CH2Cl2 (10 mL) previouslycooled in an ice bath. The mixture was allowed to gradually warmto r.t., with stirring, over 12 h. TLC and LC-MS analyses were usedto monitor reaction progress. The solution was then evaporated todryness, in vacuo at r.t., to give the crude material. The reactionmixture was purified by chromatography on silica gel (petroleumether-EtOAc, 60:40).

The synthetic route of 22503-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cannazza, Giuseppe; Perrone, Serena; Rosato, Francesca; D’Accolti, Lucia; Parenti, Carlo; Troisi, Luigino; Synthesis; vol. 46; 7; (2014); p. 962 – 966;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics