Tag: M.W=200-300

69065-91-4, These common heterocyclic compound, 69065-91-4, name is Ethyl 2-((4-fluorophenyl)amino)-2-oxoacetate, 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 1.1 g (5 mmol) of amine 1 and 5 mmol of anilido ester 6a-6f was heated for 5 h at 120-125C. The resulting solid was treated with hexane, and the precipitate was filtered off, washed with water, 10% aqueous HCl, and water again, dried in air, and recrystallized from ethanol.

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 69065-91-4.

Reference:
Article; Aghekyan; Mkryan; Muradyan; Tumajyan; Russian Journal of Organic Chemistry; vol. 54; 6; (2018); p. 886 – 891; Zh. Org. Khim.; vol. 54; 6; (2018); p. 884 – 889,6;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

847361-67-5, 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. 847361-67-5, name is 1-(4-Bromophenyl)cyclopropanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of the bromide from Step 4 (1.0 g, 4.16 mmol), commercially available 4-(dihydroxyboranyl)benzoic acid (0.73 g, 4.37 mmol), sodium carbonate (2 M aq. solution, 5.2 mL, 10.4 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) in water (8 mL) and acetontrile (12 mL) was heated to 60C and stirred overnight. The reaction mixture was cooled, filter and the mother liquors were concentrated. The residual aqueous mixture was acidified with 1 N HCl. The resultant milky suspension was filtered to provide a pale grey solid which was further dried under high vacuum to provide the title compound (1.1 g).

The synthetic route of 1-(4-Bromophenyl)cyclopropanecarboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; BLACK, Cameron; BEAULIEU, Christian; WO2010/148488; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, 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. 85006-25-3

Scheme 1: Reagent and conditions; (a) tert-butyl(tert-butoxycarbonyl)oxycarbamate, iN NaOH, TBAB, DCM; (b) TFA, DCM; (c) 3,3-difluoro-2,2-dimethylbutanoic acid, EDCI, DIEA, DMF, rt, 12h(d) NaH, Mel, THF.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 85006-25-3, its application will become more common.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; ZHANG, Zhiyuan; WANG, Xiaodong; LEI, Xiaoguang; SU, Yaning; HE, Sudan; RUAN, Hanying; SUN, Liming; (103 pag.)WO2016/101885; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

125664-95-1, A common compound: 125664-95-1, name is N-Propionyl-(2R)-bornane-10,2-sultam, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A 1 M solution of NaHMDS in THF (8.3 mL, 8.3 mmol) was added over the course of 15 min to a stirred solution of (N-propionyl)-(2R)-bornane-10,2-sultam 12 (0.20 M in THF, 41.5 mL) and TBAI (0.61 g, 1.65 mmol) at -78 C. The reaction mixture was kept at this temperature for 1 h under stirring. A solution of the allyl bromide 11 (4.98 M in HMPTA, 2.2 mL) was then added dropwise to the stirring reaction mixture. The cooling bath was replaced by an octane-liquid nitrogen bath (-50 C). The reaction mixture was stirred at -50 C for 4 h and then slowly (1 h) warmed to -25 C, quenched with water (80 mL), warmed to rt and extracted with ether (4 ¡Á 50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Compound 13 (3.58 g, 77%) was isolated by column chromatography on silica gel (petroleum ether/ethyl acetate) as a colourless viscous oil; 1H NMR (CDCl3) d 0.76 (d, J = 6.7 Hz, 3H, 6-Me), 0.89 (d, J = 6.7 Hz, 1.5H, 6-Me), 0.95 (s, 3H, CH3 in bornane), 1.04 (d, J = 5.6 Hz, 1.5H, 6-Me), 1.12 (s, 1.5H, CH3 in bornane), 1.14 (s, 1.5H, CH3 in bornane), 1.17 (t, J = 5.6 Hz, 1.5H, 2-Me), 1.19 (t, J = 5.4 Hz, 1.5H, 2-Me), 1.27-2.22 (m, 14H, 3 ¡Á CH2 in bornane, CH in bornane, CH2CH2CH2 in tetrahydropyran, 6-H), 2.39-2.50 (m, 1H, 3-H), 2.68-2.77 (m, 1H, 3-H), 3.31- 3.52 (m, 4H, CH2S, CHN in bornane, 2-H), 3.54 (d, J = 7.4 Hz, 0.5H, 5-H), 3.66 (d, J = 8.7 Hz, 0.5H, 5-H), 3.76-3.91 (m, 2H, CH2O in tetrahydropyran), 4.51 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.56 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.95-4.98 (m, 0.5H, C=CH2), 4.99-5.01 (m, 0.5H, C=CH2), 5.00-5.04 (m, 0.5H, C=CH2), 5.12-5.16 (m, 0.5H, C=CH2); 13C NMR (CDCl3) d 16.7, 17.2, 18.3, 19.1, 19.3, 19.4, 19.8, 19.9, 20.6 (¡Á 2), 20.8, 25.4, 25.5, 26.4, 28.8, 30.1 30.5, 30.8, 31.0, 32.8, 32.9, 35.1, 36.6, 37.1, 37.2, 38.4 (¡Á 2), 44.5, 44.6, 47.7 ( 2), 48.2, 48.4, 52.9, 53.1, 62.0, 62.9, 65.1, 65.4 ( 2), 84.7, 87.2, 94.4, 100.1, 112.4, 114.3, 144.4, 146.1, 172.6, 175.8; IR (CCl4) numax: 3086, 1701, 1649 cm-1. Anal. Calcd for C25H41NO5S: C, 64.21; H, 8.84. Found: C, 64.17; H, 8.76.

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, N-Propionyl-(2R)-bornane-10,2-sultam, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shklyaruck, Denis; Matiushenkov, Evgenii; Tetrahedron Asymmetry; vol. 22; 13; (2011); p. 1448 – 1454;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

22958-64-1, 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. 22958-64-1, name is 2-(4-Sulfamoylphenyl)acetic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00382] 1H NMR (400 MHz, DMSO-cfe) d 7.80 – 7.74 (m, 2H), 7.48 (d, J= 8.4 Hz, 2H), 7.41 – 7.29 (m, 3H), 7.22 – 7.15 (m, 2H), 7.07 (td, J= 8.3, 1.8 Hz, 1H), 3.95 (s, 2H), 3.75 (s, 2H), 2.81 – 2.64 (m, 8H); LC-MS Rt 0.53 min, MS m/z [M+H]+ 499.4

The synthetic route of 2-(4-Sulfamoylphenyl)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

72791-76-5, The chemical industry reduces the impact on the environment during synthesis 72791-76-5, name is Benzyl bis(2-chloroethyl)carbamate, I believe this compound will play a more active role in future production and life.

2-phenylacetonitrile (5.000 g, 42.680 mmol) and sodium hydride (60.00%, 3.755 g, 93.897 mmol) was dissolved in N,N-dimethylformamide (100 mL) at 0 C and stirred for 30 minutes then benzyl bis(2-chloroethyl)carbamate (11.787 g, 42.680 mmol) was added thereto after further stirring at 60 C for 3 hours, the reaction was terminated by lowering the temperature to room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 30% to 100%) and concentrated to give the title compound (7.500 g, 54.8%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis Benzyl bis(2-chloroethyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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 94838-59-2. 94838-59-2

A mixture of 2-Deoxy-D-ribose (Apollo, 2g, 14.8 mmol), tert-butyl 4- aminophenetylcarbamate (Ark Pharm, 5.14 g, 20.7 mmol) and montmorillonite (12 g) was stirred at RT in MeCN (100 mL) for three days. The reaction mixture was then filtered through a celite pad which was subsequently washed with EtOAc. The filtrate was concentrated under reduced pressure. Purification of this crude (5.2 g) by flash chromatography on silica (Cyclohexane: EtOAc, gradient from 7:3 to 6:4) afforded the title compounds: First eluting fraction (Intermediate 1): [2-((lS,9S,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (1.88 g, 37%), yellow solid, Rf=0.35 (Cyclohexane:EtOAc, 2:8), lH NMR (CDC13) : 6.98 (dd, IH, J=8.1 Hz, J=1.5 Hz), 6.94 (dd, IH, J=1.5 Hz), 6.59 (d, IH, J=8.1 Hz), 4.67-4.36 (m, IH), 4.60-4.50 (m, IH), 4.45-4.35 (m, IH), 3.81-3.65 (m, 2H), 3.63 (brs, IH), 3.37-3.20 (m, 2H), 2.91 (t, IH, J=10.0 Hz), 2.71-2.61 (m, 2H), 2.15-2.05 (m, 2H), 2.15-2.05 (m, 2H), 1.88 (dd, IH, J=4.7 Hz, J=2.0 Hz), 1.43 (s, 9H). Second eluting fraction (intyermediate 2): [2-((lR,9R,10S)-10-Hydroxy-12-oxa-8-aza- tricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-ethyl]-carbamic acid tert-butyl ester (2.0 g, 41%), white solid, Rf=0.25 (Cyclohexane:EtOAc, 2:8), lH NMR (CDCI3) : 7.01-6.93 (m, 2H), 6.51 (d, IH, J=8.0 Hz), 4.71-4.68 (m, IH), 4.60-4.48 (m,lH), 3.67-3.61 (m, IH), 3.59-3.48 (m, 3H), 3.38- 3.24 (m, 2H), 2.67 (t, 2H, J=7.0 Hz), 2.56 (dt, IH, J=13.5 Hz, J=3.0 Hz, J=3.0 Hz), 2.31 (d, IH, 7.3 Hz), 1.59-1.53 (m,lH), 1.43 (s, 9H).

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 tert-Butyl 4-aminophenethylcarbamate.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; JOHNSON, Theresa L.; GRAEDLER, Ulrich; JIANG, Xuliang; ROCHE, Didier; LEMOINE, Hugues; GILARDONE, Marine; (61 pag.)WO2017/173049; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112253-70-0, name is 2-Amino-4-bromobenzamide, 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. 112253-70-0

To bis(triphenylphosphine)palladium(II) dichloride (98 mg, 0.14 mmol), 2-amino-4-bromobenzamide (600 mg, 2.79 mmol), and l-methyl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (754 mg, 3.62 mmol) were added acetonitrile (9 mL) and 1M aq Na2CC>3 (9 mL, 9 mmol). The reaction vessel was evacuated and flushed with argon (3X). The mixture was heated in a microwave reactor at 160 C for 20 min. The mixture was allowed to cool to rt, the organic layer was decanted, and the aqueous layer was retained. The organic layer was concentrated under reduced pressure and the residue was diluted with water. The resulting solid was collected by filtration washing with water and acetonitrile. The retained aqueous layer from above was filtered, and the collected solid was washed with water and acetonitrile. The collected solids were combined to afford 2-amino-4-(l -methyl- 1H- pyrazol-4-yl)benzamide (520 mg, 86%). LCMS (ESI) m/z 217 (M + H)+.

Statistics shows that 112253-70-0 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-bromobenzamide.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30912; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1, 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. 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Asymmetric synthesis of (-)-2-(diphenylmethyl)sulphinylacetamideGeneral procedure for examples 1 to 10 : Diphenylmethylthioacetamide (7.70 g ; 0.03 mol ; 1.0 eq) was dissolved in the solvent (toluene ; 77 mL ; 10 vol.) under argon. To the solution were added (S,S)-(-)-diethyl-tartrate (1.23 g ; 0.006 mol; 0.2 eq) and titanium (IV) tetraisopropoxide (0.85 g ; 0.88 mL ; 0.003 mol; 0.1 eq) and water (27 muL minus the sum of water present in reactants and solvent already introduced ; 0.0015 mol ; 0.05 eq) at 55C. In these conditions, the resulting chiral titanium complex has the stoichiometry (DET/Ti(OiPr)4/H2O : 2/1/0.5) and represents 0.1 eq of diphenylmethylthioacetamide. Stirring was maintained at 55C during 50 minutes. After cooling to room temperature (25C), were added to the mixture diisopropylethylamine (0.39 g ; 0.52 mL ; 0.003 mol ; 0.1 eq) and cumene hydroperoxide (4.55 g ; 5.0 mL ; 0.03 mol ; 1.0 eq). After contacting during about an hour, the formed precipitate is isolated by filtration. All the following experiments were performed in accordance with the conditions of the general procedure, by modifying parameters as indicated in tables 1-10.; Example 2 : Influence of the amount of water on the enantioselectivity of asymmetric oxidation In this experiment, the ratio of water was varied with respect to the titanium tetraisopropoxide from 0 to 1 equivalent, all the other parameters being as defined in the above general procedure. Notably, the ratio of the titanium chiral complex was maintained at 0.1 equivalent with respect to the diphenylmethylthioacetamide. [Table 2] EntryAmount of water (equivalent)E. e. (%)Purity (%)Yield (%)1080-90.320.493> 999230.894> 9988419199.590 – = Not determined These results show that the amount of water has an effect on the enantioselectivity of the reaction. Thus, the best enantioselectivities are achieved when an amount of water comprised between 0.4 and 0.8 equivalents are used. On the opposite, the enantioselectivity drops notably in the absence of water.

The synthetic route of 2-[(Diphenylmethyl)thio]acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON FRANCE; EP1516869; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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.

p-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4-yl] benzene sulfonamide potassium salt compound of formula-7b: To a solution of 4-tert-butyl benzene sulfonamide compound of formula-6 (48 g) in toluene (600 ml), potassium carbonate (35 g) and tetra butyl ammonium bromide (10 g) was added and the reaction mixture was heated to 500C. A solution of 5-(2- methoxyphenoxy)-2-(2’pyrimidinyl)-4,6-dichloro ‘ pyrimidine compound of formula-5 (60 g) in toluene (1200 ml) was added slowly to the reaction mixture and it was refluxed using dean stark apparatus for 10 hrs. The reaction mixture was cooled to 25C.The solid obtained slurried in water and then filtered, washed with water and then dried to get the title compound. Yield: 90 gTo a solution of 4-tert-butyl benzene sulfonamide compound of formula-6 (61.3 grams) in toluene (1500 ml), potassium carbonate (77.93 grams) and tetra butyl ammonium bromide (2.77 grams) was added and the reaction mixture was heated to 50C. A solution of 5-(2-methoxyphenoxy)-2-(2’pyrimidmyl)-4,6-dichloro pyrimidine compound of formula-5a (100 grams) in toluene (1500 ml) was added slowly to the reaction mixture and it was refluxed for 10 hrs. The reaction mixture was cooled to 25C.The solid obtained was filtered and made slurry in water. The solid was filtered, washed with water followed by acetonitrile and dried. Yield: 116 grams, HPLC purity: 99.3%, MR: 202-205C.

According to the analysis of related databases, 4-(tert-Butyl)benzenesulfonamide, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MSN LABORATORIES LIMITED; WO2009/95933; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics