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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 4-(hydroxymethyl)benzylcarbamate

EXAMPLE 8-1 4- {[(tert-butoxycarbonyl)amino]methyl} benzyl(3aR, 7aR)-1 -(7H-pyrrolo[2,3-d]pyrimidin-4-yl)octahydro-4-pyrrolo[3,2-b]pyridine-4-carboxylate To a stirred solution of CDI (20 mg, 0.12 mmol) in THF (0.20 mL) was added (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (29 mg, 0.12 mmol) in THF (0.20 mL) at -10 C. The resulting suspension was allowed to stir for 1 hour at ambient temperature. In a separate flask, enantiomer 2 of Example 2 was dissolved in THF (0.20 mL) and DBU (0.019 mL, 0.12 mmol) followed by Et3N (0.017 mL, 0.12 mmol) was added and allowed to stir at ambient temperature for 5 minutes. The activated alcohol solution was added to the suspension of amine in DBU and the resulting suspension was allowed to stir at ambient temperature for 18 hours. The reaction mixture was partitioned between EtOAc (25 mL) and saturated aqueous sodium bicarbonate (25 mL). The layers were separated, and the organic layer was collected, dried over sodium sulfate, and concentrated in vacuo. The crude reaction mixture was purified by column chromatography on silica gel eluting with EtOAc/hexane (0-100%) followed by DCM:MeOH (90:10). The product fractions were concentrated in vacuo to afford the desired product. LRMS calc’d for C27H34N6O4 [M+H]+, 507; found 507. Jak1 activity: +.

The synthetic route of 123986-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
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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. 112253-70-0, name is 2-Amino-4-bromobenzamide, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrN2O

2-Amino-4-bromobenzonitrile was dissolved in 4: 1 AcOHZH2SO4 to form a suspension. The mixture was stirred for 4 h until it became clear and all starting material was consumed as monitored by LC-MS. The solution was poured into ice water and extracted by EtOAc three times. The combined organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed to provide 11-1. Substituted benzyloxy acetic acid (1.1 equiv) was treated with 2 M oxalyl chloride in DCM for 3 h and concentrated to give the corresponding acid chloride, which was then added to a stirred solution of 11-1 and pyridine (5 equiv) in DCM. The reaction mixture was stirred for 3 h until 11-1 was consumed as monitored by LC-MS. The precipitate was collected by filtration and was dried under vacuum to provide 11-2 as white solid. 11-2, potassium carbonate (4 equiv), boronic ester (1.5 equiv) and Pd(PPh3 )4( 10%) were dissolved in 4: 1 dioxane/water and sealed in a microwave tube. The reaction mixture was degassed and heated by microwave for 30min at 140 0C. The solvent was removed and the residue was subjected to preparative HPLC to provide product 11-3 as a TFA salt.

The synthetic route of 112253-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; LOGRASSO, Philip; BANNISTER, Thomas; SCHROETER, Thomas; FANG, Xingang; YIN, Yan; CHEN, Yen Ting; SESSIONS, Hampton; CHOWDHURY, Sarwat; LUO, Jun-Li; VOJKOVSKY, Tomas; WO2010/56758; (2010); 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. 96-72-0, name is 2-Chloro-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 96-72-0

An aqueous solution of NaOH (3.66 g; 92 mmol; 10% w/v) was added to a solution of 3-iodophenol (18.30 g; 83 mmol) in acetone (130 mL). Evaporation under reduced pressure afforded the crystals of the sodium salt 5, which were added to a solution of sulfonamide 4 (3.94 g; 17 mmol) in acetonitrile (24 mL). The mixture was refluxed and potassium carbonate (1.62 g; 12 mmol) was added. After completion of the reaction (48 h, monitored by TLC), the solution was acidified using 12M HCl, diluted with water and extracted with ethyl acetate (¡Á3). The combined organics were dried (MgSO4), and concentrated in vacuo. The crude product was purified using column chromatography (SiO2; pentane/ethyl acetate, 3:1), yielding the title compound 6 as a colorless solid (5.84 g; 84%). M.p. 153-155 C. (lit. 153-154 C.).

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 96-72-0.

Reference:
Patent; University College Dublin, National University of Ireland, Dublin; Kinsella, B. Therese; Reid, Helen; (104 pag.)US2016/102051; (2016); A1;,
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Application of 56987-35-0, These common heterocyclic compound, 56987-35-0, name is 3,3-Dibromo-azepan-2-one, 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 3,3-dibromoazepan-2-one (15.7 g, 57.9 mmol) in piperidine (140 mL) was heated at reflux for 4.5 h under N2. The solution was then allowed to reach room temperature and washed with 0.50 M aq. NaHS03 (200 mL). The aqueous phase was extracted with CHC13 (3 x 100 mL) and the combined organic layers were washed with brine (1 x 300 mL), dried (MgS04) and concentrated to afford a brown, oily solid, that crystallized upon standing. The resulting solid was suspended in water, filtered, and washed with water and Et20 to give 1 (10.3 g, 91%) as a white solid: IR (ATR, neat) 3193, 2950, 2935, 2923, 2855, 1655, 1605 cm”1; 1H NMR (CDC13, 600 MHz) delta 6.51 (bs, 1 H), 5.06 (t, 1 H, J= 7.6 Hz), 3.22 (q, 2 H, J= 6.5 Hz), 2.78 (app t, 4 H, J= 5.3 Hz), 2.15 (q, 2 H, J= 7.2 Hz), 1.76 (app quint, 2 H, J= 6.8 Hz), 1.69-1.62 (m, 4 H), 1.54-1.48 (m, 2 H); 13C NMR (CDC13, 150 MHz) delta 171.5, 147.6, 105.4, 50.1, 39.5, 30.2, 25.5, 24.5, 21.5; HRMS (EI) m/z calcd for CiiH18N20 194.1419, found 194.1422.

Statistics shows that 3,3-Dibromo-azepan-2-one is playing an increasingly important role. we look forward to future research findings about 56987-35-0.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; WANG, Qiming, Jan; WO2012/78859; (2012); A2;,
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Electric Literature of 478837-18-2, 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. 478837-18-2 name is tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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.

To a solution of tert-butyl 3-hydroxy-8-azabicyclo [3.2.1] octane-8-carboxylate (2 g, 8.80 mmol) and triethylamine (1.84 mL, 13.20 mmol) in dichloromethane (10 mL) Was added and stirred at 0 C, methanesulfonyl chloride (0.817 mL, 10.56 mmol) was added and reacted for 2 hours. The solvent was removed from the resulting mixture under reduced pressure, and the reaction mixture was extracted with dichloromethane (40 mL), dried using anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. The obtained organic layer was purified by silica gel flash column chromatography (ethyl acetate: hexane = 1: 4) to obtain tert-butyl 3- (methylsulfonyloxy) -8-azabicyclo [3.2.1] octane-8-carboxylate 92.4%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; NOH, Eun Joo; SIM, Tae Bo; AHN, Dae Ro; CHOI, Seung Ho; (25 pag.)KR101683061; (2016); B1;,
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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. 79722-21-7, name is tert-Butyl benzyloxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 79722-21-7

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

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 79722-21-7.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
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Some common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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 4-(tert-Butyl)benzenesulfonamide

General procedure: To a solution of 12 3,4-diphenyl-1H-pyrrole-2,5-dione 4b (4.96mmol) in 83 CH3CN (20mL), 84 K2CO3 (4.96mmol), 85 TBAB (0.5mmol) and 16 1,4-dibromobutane (19.84mmol) were added and the mixture was stirred at 45¡ãC overnight. Solvent was evaporated to dryness, 86 water (50mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and solvent evaporated to dryness. 17 8 was obtained by a silica gel column chromatography. The solution of 88 BBr3 (1M, 9.47mmol) in anhydrous 89 CH2Cl2 was added to compound 17 8 (3.94mmol) in 20mL anhydrous CH2Cl2 under nitrogen atmosphere at ?78¡ãC. The mixture was stirred at ?78¡ãC for 1h. The temperature rised to 0¡ãC, 10mL 90 H2O was added and the resulting solution was stirred for 0.5h and extracted with ethyl acetate. Collected organic layers were washed with brine and dried over anhydrous Na2SO4, and solvent was evaporated to dryness to afford compound 18 9, a yellow solid with sufficient purity to be used without further purification. To a solution of 18 9 (1.86mmol) and 84 K2CO3 (2.28mmol) in 10mL 92 acetone, methyl bromoacetate was added. The reaction proceeded reflux overnight and was added 30mL 86 water. Then, the mixture was extracted with ethyl acetate and dried over anhydrous Na2SO4. The residue was purified by a silica gel column chromatography to give 93 10. K2CO3 (1.76mmol), KI (1.32mmol), substituted aromatic sulfonamide (1.32mmol) and compound 10 were added to 2mL CH3CN. The mixture was stirred reflux overnight, and solvent was concentrated, H2O (12mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and evaporated. 11 was obtained by a silica gel column chromatography. 1M aqueous solution of LiOH (1.11mmol) was added to the solution of compound 11 (0.742mmol) in 4mL THF at ?5¡ãC. The mixture was stirred at ?5¡ãC until complete by TLC and adjusted to pH 5 by 1M HCl. The resulting mixture was extracted with diethyl ether, and the organic layer was wash by brine and dried over anhydrous Na2SO4. The solution was evaporated to afford compound 12. To a solution of glycylglycine methyl ester hydrochloride (0.81mmol) and DIPEA (1.62mmol) in 5mL CH3CN, 12 (0.67mmol), HOBt (0.81mmol) and EDCl (0.81mmol) were added at 0¡ãC. The mixture proceeded at 50¡ãC overnight, diluted with CH2Cl2 and washed with brine. The organic layer was dried over anhydrous Na2SO4 and evaporated. Compound 13 was obtained by the silica gel column chromatography. For the synthesis of 14a-j, Et3N (0.866mmol) and LiCl (0.94mmol) were added to the solution of compound 13 in 5mL CH3CN: H2O (95: 5) at 0¡ãC. The solution was adjusted to pH 5 by 1M HCl and evaporated by CH2Cl2. Combined organic layer was washed by brine, dried over anhydrous Na2SO4 and concentrated. The resulting residue was triturated with ethyl acetate and filtrated to give target compound 14a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6292-59-7, its application will become more common.

Reference:
Article; Yuan, Xinrui; Xia, Yineng; Lu, Peng; Zhu, Lijuan; Zhong, Yuejiao; Wang, Yubin; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1435 – 1447;,
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Some common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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. Recommanded Product: 94838-59-2

Z-Phe-Cit (9.13 g, 20 mmol) was charged into a mixture of dichloromethane (750 mL) and isopropanol (250 mL) and then stirred until the dipeptide was completely dissolved. Then, APEA-Boc (7.09 g, 30 mmol) and EEDQ (7.42 g, 30 mmol) were added and the mixture was stirred at room temperature for 3 days. The solvents were removed under reduced pressure and then diethyl ether (300 mL) was added to the residue. The mixture was filtered off and the crude product was re-suspended in diethyl ether (300 mL). This procedure was repeated 3 times. The collected solid product was finally dried under vacuum to afford Z-Phe-Cit-APEA-Boc (9.53 g, yield 70.6%). The product was characterized by PMR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 94838-59-2, its application will become more common.

Reference:
Patent; Industrial Technology Research Institute; KO, Yi-Ju; LI, Jheng-Sian; LU, Maggie; LEE, On; CHENG, Ping-Fu; LIU, Chun-Min; (74 pag.)US2017/119902; (2017); A1;,
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Electric Literature of 112253-70-0, A common heterocyclic compound, 112253-70-0, name is 2-Amino-4-bromobenzamide, molecular formula is C7H7BrN2O, 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 5.25c. Synthesis of (9H-fluoren-9-yl)methyl 2-(5-bromo-2- carbamoylphenylcarbamovDpyrrolidine- 1 -carboxylateA solution of (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine- l-carboxylate (600 mg, 1.8 mmol), 2-amino-4-bromobenzamide (400 mg, 1.8 mmol), and Et3N (2 mL) in THF was stirred at room temperature . The reaction was monitored by TLC. After diluting with H20 (50 mL), the mixture was extracted with ethyl acetate (3 x 100 mL). The organic layers were dried over Na2S04 and concentrated to give yellow residue, which was purified by column chromatography. MS (ESI): 534, 536(MH+)

The synthetic route of 112253-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; HARDY, Larry, Wendell; HEFFERNAN, Michele, L., R.; WU, Frank, Xinhe; SPEAR, Kerry, L.; SARASWAT, Lakshmi, D.; WO2011/75699; (2011); A2;,
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Electric Literature of 22117-85-7, 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. 22117-85-7, name is 2-Methoxy-5-sulfamoylbenzoic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 72 5-(Aminosulfonyl)-2-hydroxybenzoic acid A mixture of 2-methoxy-5-sulfamoylbenzoic acid (58 g, 0.25 mole), 48% hydrobromic acid (150 ml), and acetic acid (150 ml) was heated to reflux for five hours. The progress of reaction was checked by thin layer chromatography (silica gel, 7:2:1 ethylacetate/methanol/29% ammonium hydroxide). Upon cooling, a solid crystallized out which was collected by filtration, and rinsed with cold water. This solid was dissolved in hot water (?85 C.) and filtered through Celite and recrystallized from the cool filtrate. Some of the recrystallized material was crystallized once more by dissolving in methanol, filtering, and mixing with excess amount of 1,1,1-trichloroethane. The mixture was evaporated to remove most of the methanol, and the resulting crystallizing mixture was stirred in ice bath. The solid was collected by filtration and rinsed with 1,1,1-trichloroethane, vacuum pumped at room temperature overnight to give a white solid, mp 234-235 C. Analysis: Calculated for C7 H7 NO5 S: C, 38.71; H, 3.25; N, 6.45. Found: C, 38.53; H, 3.19; N, 6.41.

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, 2-Methoxy-5-sulfamoylbenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; A. H. Robins Company, Incorporated; US4990523; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics