Tag: M.W=300-400

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. 214973-83-8, name is tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate, A new synthetic method of this compound is introduced below., Product Details of 214973-83-8

370 ml (350 mmol) of a 0.95 M sec-butyl lithium/n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of 1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene (Reference Compound 4-1) in 800 ml of diethyl ether at -78 C. in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was added dropwise thereto at -78 C. and the mixture was stirred at -50 C. for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane:ethyl acetate=4:1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144 C. Rf value: 0.38 (n-hexane:ethyl acetate=4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)

The synthetic route of 214973-83-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Seike, Hisayuki; Matsugi, Takeshi; Shimazaki, Atsushi; US2009/12123; (2009); 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. 191170-76-0, name is Benzyl 4-bromophenethylcarbamate, A new synthetic method of this compound is introduced below., SDS of cas: 191170-76-0

(1402) [00449] To a vial was added benzyl 4-bromophenethylcarbamate (0.337 g, 1.01 mrnol), tert- butyl 3,6-diazabicyclo[3.1.1]heptane-3-carboxylate (0.200 g, 1.01 mmoi), CS2CO3 (0.822 g, 2.52 mmoi), and XPhos Pd 2nd generation precatalyst (0.079 g. 0.10 mmoi). The vial was backfilled with dry nitrogen 3 times. Dioxane (2 ml) was added to the solid mixture and a stream of dry nitrogen was bubbled through the reaction for 2 minutes. The reaction mixture was heated to 90 C overnight and then cooled to RT, filtered through Celite and concentrated in vacuo. The resulting crude product was purified by FCC eluting with 20 – 30% EtOAc in hexanes to afford teri-mXy 6-(4-(2-(((benzyloxy)carbonyl)amino)ethyl)phenyl)-3,6-diazabicyclo[3.1 .1 ]heptane~3- carboxylate as a white solid (322 mg, 71%). LCMS (ESI, m/z): 452 [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; 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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Related Products of 597563-17-2, These common heterocyclic compound, 597563-17-2, name is tert-Butyl (1-(3-bromophenyl)cyclopropyl)carbamate, 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.

EXAMPLE 106; Step 1; Epoxide opening with 1- (3-bromophenyl) cyclopropyl amine; N-BOC-1- (3-bromophenyl) aminocyclopropane (15.60g, 50.2 mmol) was treated with 4N HC1 in dioxane (50 mL) and stirred for 2 h. The volatiles were evaporated in vacuo and the residue taken up into 1N NaOH (250 mL). The mixture was extracted with diethyl ether (2 X 200 mL). The combined ether extracts were washed with brine (50 mL), dried (sodium sulfate), then filtered and evaporated in vacuo to provide the amine free base. The amine free base was dissolved in 2-propanol (250 mL) and the epoxide (15. 0g, 50.2 mmol) was added. The mixture was heated to reflux for 22 h and allowed to stand at ambient temperature for 3 d. Analysis by HPLC indicated that the desired product predominated, and that some starting cyclopropylamine remained unreacted. The starting epoxide was consumed. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (eluted 2: 1 hexane/ethyl acetate) to provide the final product (13.68 g, 53%).

The synthetic route of 597563-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
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Synthetic Route of 24310-36-9,Some common heterocyclic compound, 24310-36-9, name is 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydrobenzo[b]azepin-5-one, molecular formula is C17H17NO3S, 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.

Step 2. Preparation of (+/-) (3, 5-Bis-trifluoromethyl-benzyl)- [1- (toluene-4-sulfonyl)- 2,3, 4, 5-tetrahydro-1H-benzo [b] azepin-5-yl]-amine. A mixture of (+/-) 1- (Toluene-4-sulfonyl)-1, 2,3, 4-tetrahydro-benzo [b] azepin-5- one (500 mg, 1.58 mmol), 3,5-Bis (trifluoromethyl) benzylamine (423 mg, 1.74 mmol) and titanium (IV) isopropoxide (0.59 ml, 1.97 mmol) in diglyme (2 ml) is stirred at room temperature for 22 hours. The mixture is diluted with methanol (7 ml) and treated with sodium borohydride (90 mg, 2.37 mmol), then stirred at room temperature for 6 hours. The mixture is treated with 0. 1N aqueous NaOH (15 ml) and stirred for 10 minutes, then filtered. The filter cake is washed with 1: 1 ethanol : diethyl ether. The filtrate is diluted with water (70 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated to an oil. The oil is < purified by silica gel column chromatography (eluent, 15 % ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 543 (M+H). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydrobenzo[b]azepin-5-one, its application will become more common. Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
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316146-27-7, name is N-(4-Bromophenyl)-3-phenylpropanamide, 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. Computed Properties of C15H14BrNO

Intermediate 2 The reaction was carried out twice . POCI3 (1.225 mol) was added dropwise at 10 0C to DMF (0.525 mol) . Then intermediate 1 (0.175 mol) was added at room temperature. The mixture was stirred overnight at 80 0C, poured out on ice and extracted with CH2CI2 . The organic layer was dried (MgSO/t), filtered, and the solvent was evaporated, yielding 77.62 g (67percent) of intermediate 2. The product was used without further purification.

The synthetic route of 316146-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/14934; (2007); A2;,
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These common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, 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. Quality Control of N-Boc-2-(4-Bromophenyl)ethylamine

A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 4-methoxyphenylboronic acid (0.61?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol), Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14j as a white solid (0.52?g, 58%): Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 3.02-3.05 (m, NH3CH2CH2), 3.82 (OCH3), 6.93 (d, J?=?8.1?Hz, 1 ArH), 7.18-7.23 (m, 2 ArH), 7.35-7.40 (m, 3 ArH), 7.64 (d, J?=?6.8?Hz, 2 ArH), 8.37 (s, NH3); 13C NMR (DMSO-d6, 75?MHz) delta 33.0 (NCH2CH2), 55.6 (CH3), 112.5, 113.4, 119.3, 127.4, 129.7, 130.4, 137.4, 138.9, 141.9, 160.2 (12 ArC).

The synthetic route of N-Boc-2-(4-Bromophenyl)ethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yeon, Seul Ki; Choi, Ji Won; Park, Jong-Hyun; Lee, Ye Rim; Kim, Hyeon Jeong; Shin, Su Jeong; Jang, Bo Ko; Kim, Siwon; Bahn, Yong-Sun; Han, Gyoonhee; Lee, Yong Sup; Pae, Ae Nim; Park, Ki Duk; Bioorganic and Medicinal Chemistry; vol. 26; 1; (2018); p. 232 – 244;,
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Synthetic Route of 120157-97-3, A common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, molecular formula is C13H18BrNO2, 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: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 3-fluorophenylboronic acid (0.56?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol), Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14d as a white solid (0.52?g, 62%); Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 2.98-3.09 (m, NH3CH2CH2), 7.17-7.52 (m, 6 ArH), 7.68 (d, J?=?8.0?Hz, 2 ArH), 8.34 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.0 (NCH2CH2), 113.6 (d, JC-F?=?21.8?Hz), 114.5 (d, JC-F?=?20.9?Hz), 123.0 (d, JC-F?=?2.4?Hz), 127.4, 129.8, 131.3 (d, JC-F?=?8.5?Hz), 137.6 (d, JC-F?=?2.1?Hz), 137.9, 142.8 (d, JC-F?=?7.7?Hz), 163.2 (d, JC-F?=?241.7?Hz) (12 ArC).

The synthetic route of 120157-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yeon, Seul Ki; Choi, Ji Won; Park, Jong-Hyun; Lee, Ye Rim; Kim, Hyeon Jeong; Shin, Su Jeong; Jang, Bo Ko; Kim, Siwon; Bahn, Yong-Sun; Han, Gyoonhee; Lee, Yong Sup; Pae, Ae Nim; Park, Ki Duk; Bioorganic and Medicinal Chemistry; vol. 26; 1; (2018); p. 232 – 244;,
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Synthetic Route of 1195768-19-4, 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 1195768-19-4 as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, l.OlmL, l.Olmmol) was added to a cooled (0C) solution of Methyl 3-((2,6-difluorophenyl)sulfonamido)-2- fluorobenzoate (lOOmg, 0.29mmol) in THF (2.5mL). After lOmin of stirring, a solution of 4-Methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (76mg, 0.29mmol) in THF (lmL) was slowly added and the reaction mixture was allowed to warm to room temperature. After 2 hours of stirring, saturated aqueous ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (two times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure to afford the title compound (170mg, quant) as a mixture of ketone and enol. LC/MS (ES+): 577.4 (M+l).

According to the analysis of related databases, 1195768-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); 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. 299430-87-8, name is (9H-Fluoren-9-yl)methyl (2-(2-hydroxyethoxy)ethyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., name: (9H-Fluoren-9-yl)methyl (2-(2-hydroxyethoxy)ethyl)carbamate

To Example 2.62.3 (5.03 g) and triphenylphosphine (4.62 g) in toluene (88 mL) wasadded di -tert-butyl-azodicarboxylate ( 4.06 g) and the reaction was stirred for 30 minutes. (9H-20 Fluoren-9-yl)methyl (2-(2-hydroxyethoxy)ethyl)carbamate was added and the reaction was stirred for25an addition 1.5 hours. The reaction was loaded directly onto silica gel and was eluted with 1-50%ethyl acetate/heptanes to provide the title compound.

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 299430-87-8.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; SOUERS, Andrew, J.; PHILLIPS, Andrew, C.; JUDD, Andrew, S.; BRUNCKO, Milan; (717 pag.)WO2017/214282; (2017); A1;,
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159790-81-5, name is (9H-Fluoren-9-yl)methyl 4-aminobenzylcarbamate, 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: 159790-81-5

N-Fmoc-para-(aminomethyl)phenylazobenzoic acid was prepared adapting literature procedures [1]. Para-nitrosobenzoic acid [2] (0.94 g, 6.2 mmol) and N-Fmoc-para-aminobenzylamine [3] (1.06 g, 3.1 mmol) were suspended in acetic acid/DMSO 1:1 (80 mL) and stirred at room temperature for 48 h. Water was added to the reaction mixture, the precipitate was filtered, washed with water several times, dried, and recrystallized from acetone/water mixtures yielding the desired azo compound (660 mg, 45%) as an orange solid.

The synthetic route of 159790-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ponader, Daniela; Igde, Sinaida; Wehle, Marko; Maerker, Katharina; Santer, Mark; Bleger, David; Hartmann, Laura; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1603 – 1612;,
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