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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H6F3NO2S

Dissolve 2,6-dimethoxynaphthalene 37.6 g (0.20 mol) and 4-(2-(piperidin-1- yl) ethoxy) benzoyl chloride 64.0 g (0.21 mol) in 800 mL of dichloromethane. Add aluminum chloride 133 g (1.00 mol) portionwise and slowly (the first 30 to 50 g must be added slowly to keep the acylation reaction under control so the solvent does not boil off). After all the aluminum chloride has been added, stir the reaction until no more undemethylated compound can be detected either by TLC or HPLC (about 5 hours). Slowly pour the reaction mixture into 1 L of ice/water with vigorous stirring. Decant the top layer water into a separation funnel. Wash the dichloromethane solution and the precipitate with 2N HCl and decant the aqueous layer again into the separation funnel. Extract the aqueous layer with dichloromethane. Adjust the combined dichloromethane solution and the precipitate pH to 8 first with IN NaOH then with saturated NaHCO3. Filter the mixture. Slurry the solid repeatedly with dichloromethane. Separate the layers of the filtrate and extract the aqueous phase with dichloromethane. Wash the combined organic with brine and dry over MgS04. Treat the dichloromethane solution with charcoal and filter through a prepackaged”suppelco”silica gel funnel. Evaporate the solvent to give 61.2 g (75.5%) of 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-benzoyl]- naphthalen-2-ol. Couple 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-ol and 2,4-dibenzyloxyphenyl boronic acid to provide 2- (2, 4-dibenzyloxyphenyl)-6-methoxy-l- [4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalene by the procedure analogous to that described above in the procedure for 5- {6-benzyloxy-1- [4- (2-piperidin-1-yl-ethoxy)- phenoxy]-naphthalen-2-yl}-2-methyl-isoindole-1, 3-dione. Dissolve 10.5 g (20.0 mmol) 2- (2, 4-dibenzyloxyphenyl)-6-methoxy-l- [4- (2- piperidin-1-yl-ethoxy)-benzoyl]-naphthalene in 150 mL of THF. Add LAH 1.5 g (37.0 mmol) portionwise with vigorous stirring at 0 C. After the addition, allow the reaction to warm up to room temperature and then stir for 3 hours. Cool the reaction in an ice bath and slowly quench with saturated Na2SO4. Filter off the solid A1203 and wash the filter cake with THF (2x50mL). Combine the filtrates, concentrate and purify the residue by flash chromatography on silica gel using CH2Cl2 : MeOH (9: 1) as eluent to afford 2- methoxy-5- {hydroxy- [4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2, 4- benzyloxyphenyl)-naphthalene. Heat 2-methoxy-5- {hydroxy- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6- (2, 4- benzyloxyphenyl) -naphthalene to 60C in THF containg 10% (by weight) of Pd/C (30%) catalyst, overnight under 50 psi of hydrogen atmosphere to afford 2-methoxy-5- {hydroxy- [4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2-hydroxy-4-benzyloxyphenyl)- naphthalene. Treat the THF solution of 2-methoxy-5- {hydroxy- [4- (2-piperidin-1-yl- ethoxy)-phenyl]-methyl}-6- (2-hydroxy-4-benzyloxyphenyl)-naphthalene with 10% (by mol) of concentrated HCl to give I-12- [4- (8-benzyloxy-2-methoxy-5H-6-oxa-chrysen-5- yl)-phenoxy]-ethyl}-piperidine. Dissolve 1- {2- [4- (8-benzyloxy-2-methoxy-5H-6-oxa-chrysen-5-yl)-phenoxy]- ethyl}-piperidine (680 mg) in a mixture of 250 ml ethanol and 150 ml THF with warming. Add a slurry of 300 mf 10 % Pd/C in ethanol and react under 1 atmosphere of hydrogen for 18 hours. Filter the catalyst and evaporate the solvent to yield 465 mg of 2- methoxy-5- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-8-ol. Dissolve 2-methoxy-5- [4- (2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-8- ol (118 mg. , 0.245 mmoles) in 20 ml methylene chloride and add N- phenyltrifluoromethanesulfonimide (400 mg, . 1.12 mmoles) followed by 1.0 ml of diisopropylethyl amine and stir for 72 hours. Evaporate the solution to a paste and purify by running through an SCX column in methanol (elute with 2N ammonia/methanol) to give 125 mg of the title compound: 125 mg (83%).

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; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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Electric Literature of 71026-66-9, 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. 71026-66-9 name is tert-Butyl (4-aminophenyl)carbamate, 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.

General procedure: To a solution of 2-chloroethanesulfonyl chloride (1.56 g, 9.57 mmol) in THF (10 mL) was added dropwise N-methylaniline (989 mg, 9.23 mmol) followed by triethylamine (5 mL, 36 mmol) at 0 C. After stirring for 3 h, ethyl acetate was added, and the reaction mixture was washed with 3 M hydrochloric acid then brine, dried over magnesium sulfate, evaporated in vacuo to obtain 1.76 g (97%) of vinylsulfonamide 3a as a pale brown solid. The product was spectroscopically pure, and was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (4-aminophenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Article; Kihara, Nobuhiro; Mitsuhashi, Yuji; Sato, Makoto; Hirose, Shun-Ichi; Goudo, Erika; Uzawa, Yoshinori; Shirai, Natsumi; Hamamoto, Sari; Iwasaki, Ryo; Fujioka, Akane; Tetrahedron Letters; vol. 57; 23; (2016); p. 2563 – 2566;,
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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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, A new synthetic method of this compound is introduced below., Computed Properties of C8H12N2O2S

General procedure: (10 mmol) of 3,4-dimethoxyphenethylamine (1.1 mmol) and DIPEA (2.2 mmol) was slowly added to a THF solution (10 ml) of triphosgene (0.44 mmol) And stirred for 30-45 minutes. Then, a solution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.1 mmol) in THF (10 ml) was added and stirred overnight. The salt was filtered, and the filtrate was evaporated and column chromatography (EA: Hexane) was carried out to obtain the title compound.

The synthetic route of 35303-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
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Electric Literature of 153248-46-5, A common heterocyclic compound, 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, molecular formula is C10H19NO3, 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.

To a solution of PPh3 (242 mg, 0.92 mmol) in anhydrous tetrahydrofuran (10 mL) was added DIAD (186 mg, 0.92 mmol) by syringe at 05 C, followed by a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (185 mg, 0.92 mmol) in anhydrous tetrahydrofuran (5 mL). The resulting mixture was poured into a solution of compound 308-3 (100 mg, 0.306 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature and stirred for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 5/1) to afford the title compound 309-13 as a yellow solid (400 mg, crude). LCMS: 510.5 [M+1] .

The synthetic route of 153248-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 129686-16-4, name is 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, 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 129686-16-4, Application In Synthesis of 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one

b) (E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide According to the procedure of Preparation 2 (a), except substituting N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (0.90 g, 3.96 mmole) for benzyl acrylate, and substituting 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.60 g, 2.64 mmole) for 2-amino-5-bromopyridine, the title compound (0.85 g, 86%) was prepared as an off-white solid: MS (ES) m/e 375 (M + H)+.

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; Affinium Pharmaceuticals, Inc.; EP1226138; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 317595-54-3, The chemical industry reduces the impact on the environment during synthesis 317595-54-3, name is tert-Butyl (2-aminocyclohexyl)carbamate, I believe this compound will play a more active role in future production and life.

To a solution of N-(tert-butoxycarbonyl)-1,2-cyclohexanediamine (200 mg) and 3-((benzyloxycarbonyl)amino)propionaldehyde (65 mg) in methylene chloride (4 mL), sodium triacetoxyborohydride (133 mg) and acetic acid (18 muL) were added at room temperature, and the mixture was stirred at the same temperature for 5 hours and 30 minutes. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (2-((3-((benzyloxycarbonyl)amino)propyl)amino)cyclohexyl)carbamate (C39, 137 mg). [0841] MS m/z (M+H): 406.3

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-aminocyclohexyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJIFILM CORPORATION; TAKASAKI, Masaru; TSUJINO, Toshiaki; TANABE, Shintarou; OOKUBO, Megumi; SATO, Kimihiko; HIRAI, Atsushi; TERADA, Daisuke; INUKI, Shinsuke; MIZUMOTO, Shinsuke; US2015/45339; (2015); A1;,
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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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromomethylbenzenesulfonamide

Example 7 4-(trityithiomethyi)benzenesulfonamide To a stirred solution of triphenylmethanethiol (0.276g, 2equiv) in N,N- dimethylformamide (3 mL) at 0¡ãC was added sodium hydride (60percent w/w dispersion in mineral oil, 0.04g, 2 equiv). When the effervescence had ceased, 4- (bromomethyi)benzenesuifonamide (0.125g, 1 equiv) was added in a single portion and the reaction was allowed to warm to room temperature. HPLC-MS at 20 minutes indicated that conversion was complete. The reaction was quenched with acetic acid (-0.2 mL), concentrated to dryness in vacuo and the subsequent residue partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgS04, filtered, concentrated and purified by flash chromatography (0-50percent ethyl acetate in hexanes). Fractions containing the desired material were concentrated to dryness to furnish the desired compound as a colourless solid (0.200g). f H NMR (400MHz, DMSO-d6) delta (ppm) H), 7.36-7.44 (m, 12H), 7.67-7.73 (m, 2H)

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; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; WINTERS, Geoffrey C.; MANDEL, Alexander Laurence; RICH, James R.; HEDBERG, Bradley John; HSIEH, Tom Han Hsiao; BOURQUE, Elyse Marie Josee; BABCOOK, John; WO2014/144871; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 143557-91-9,Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

After dissolving (endo)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (CAS 143557-91-9) (2.00 g) and 1-(3-chloropropyl)-2-fluorobenzene (CAS 110406-96-7) (1.67 g) in N,N-dimethylformamide (10 ml), tetra-n-butylammonium iodide (325 mg) was added to the solution. Sodium hydride (60% in oil) (422 mg) was added and the mixture was stirred at room temperature for 17 hours and 30 minutes. Sodium hydride (60% in oil) (352 mg) was added to the reaction mixture, and stirring was continued for 2 hours at room temperature. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (1.20 g).1H-NMR (400 MHz, CDCl3); delta 1.46 (s, 9H), 1.81-1.95 (m, 8H), 2.06-2.11 (m, 2H), 2.71-2.75 (m, 2H), 3.37-3.38 (m, 2H), 3.54-3.56 (m, 1H), 4.10-4.18 (m, 2H), 6.98-7.07 (m, 2H), 7.14-7.21 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/270369; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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 1314538-55-0, Product Details of 1314538-55-0

84- iii (0.27 g, 0.45 mmol, 1 .0 equiv), potassium (((tert-butoxycarbonyl) amino) methyl) trifluoroborate (0.21 g, 0.89 mmol, 2.0 equiv) were added to toluene: water (5: 0.5) and the reaction mixture was degassed for 5 minutes. Pd (ll)OAc (0.005 g, 0.022 mmol, 0.05 equiv), RuPhos (0.02 g, 0.044 mmol, 0.1 equiv), K2CO3 (0.19 g, 1 .34 mmol, 3.0 equiv) were added and the reaction mixture was stirred at 80 C for 24 hours. The reaction mixture was quenched with cold water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by preparative HPLC purification to afford the desired product 85-i (0.038 g, 15 % yield). 1H NMR (400 MHz, MeOD) delta 7.27 (s, 1 H), 7.09 (s, 1 H), 6.43 (s, 1 H), 4.49 (s, 2H), 3.96 – 3.80 (m, 2H), 3.53 (dd, J = 18.0, 5.8 Hz, 5H), 2.47 (s, 3H), 2.23 (d, J = 7.5 Hz, 1 H), 2.18 (d, J = 7.7 Hz, 1 H), 1 .48 (d, J = 10.2 Hz, 18H), 1 .15 (d, J = 5.5 Hz, 1 H), 0.90 (d, J = 7.1 Hz, 1 H), 0.53 – 0.43 (m, 2H) LCMS (m/z): 581 .5 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FIDALGO, Javier De Vicente; HE, Haiying; HU, Cheng; JIANG, Zhigan; LI, Xiaolin; LU, Peichao; MERGO, Wosenu; MUTNICK, Daniel; RECK, Folkert; RIVKIN, Alexey; SKEPPER, Colin Kevin; WANG, Xiaojing Michael; XIA, Jianhua; XU, Yongjin; (285 pag.)WO2016/20836; (2016); A1;,
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Electric Literature of 202207-79-2, 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. 202207-79-2, name is 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Chloro-5- { [2-oxo- 1 -( lH-pyrazolo[3 .4-&]pyridin-3-ylmethyl)-4-(trifluoromethyl)-l,2-dihydropyridin-3-yl)oxy}benzonitrile_(6.0 g, 13.46 mmol) was stirred in DMA (140 mL) until dissolved and then cooled over ice bath for 10 minutes. This solution was treated with diisopropylethylamme (4.70 mL, 26.9 mmol) and then 4-nitrophenyl chloroformate (3.26 g, 16.15 mmol) portionwise over 5 minutes. This mixture was allowed to warm to room temperature and then stirred for 30 minutes. Formation of the intermediate carbamate was monitored by queching a small aliquot of the reaction mixture with dimethylamine and monitoring by LC-MS. The reaction mixture was then recooled over an ice bath and the cooled mixture was treated with a solution of 2-[(/er/-butoxycarbonyl)amino]-N-methylethanaminium chloride (3.40 g, 16.15 mmol) and diisopropylethylamme (2.5 mL, 14.3 mmol) in DMA (35 mL). Upon completion of addition, the cooling bath was removed and the mixture stirred for 1 hour at room temperature. This mixture was partitioned between ethyl acetate (1000 mL and 500 mL) and water (500 mL). The combined extracts were further washed with water (3x 00 mL), dried over MgS04, filtered and the solvent removed by evaporation in vacuo. This residue was pre- absorbed onto silica gel (35 g) using ethyl acetate and purified by silica gel (330 g)chromatography eluting with 0-100% ethyl acetate in hexanes. The desired fractions were combined and then solvent was removed by evaporation in vacuo. The resulting residue was further purified by re-crystallizing from ethyl acetate (75 mL) to give the title compound as a white solid. lH NMR (CDCI3) delta-8.68 (d, 1H), 8.26 (d, 1H, J = 7 Hz), 7.72 (d, 1H), 7.39 (dd, 1H, J=1.5Hz), 7.30 (dd, 1H5 3=4.6 and 8Hz), 7.16 (dd, 1H, J=2Hz), 7.02 (dd, 1H, J=1.3 and 2.3 Hz), 6.46 (d, 1H, J=7 Hz), 5.18 (bs t, 1H), 5.50 (s, 2H), 3.7 (br, 2H), 3.52 (br, 2H), 3.17 (s, 3H) and 1.44 (s, 9H) ppm. LRMS (M+l): 646.1

The synthetic route of 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JOLLY, Samson, M.; ANTHONY, Neville; GOMEZ, Robert; DUBOST, David, C.; WOODWARD, Rick, G.; WO2011/126969; (2011); A1;,
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