Month: September 2021

These common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, 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. COA of Formula: C5H11NS

Step C: N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(l, l-dimethylethyl)-l,3-thiazol-4-yl]- 2-fluorophenyl}-2,6-difluorobenzenesulfonamide To a reactor vessel was charged N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2- fluorophenyl}-2,6-difluorobenzenesulfonamide (30 g, 1 eq) followed by dichloromethane (300 mL). The reaction slurry was cooled to ~10C and N-bromosuccinimide (“NBS”) (12.09 g, 1 eq) was added in 3 approximately equal portions, stirring for 10-15 minutes between each addition. After the final addition of NBS, the reaction mixture was warmed to ~20C and stirred for 45 min . Water (5 vol) was then added to the reaction vessel and the mixture was stirred and then the layers separated. Water (5 vol) was again added to the dichloromethane layer and the mixture was stirred and the layers separated. The dichloromethane layers were concentrated to -120 mL. Ethyl acetate (7 vol) was added to the reaction mixture and concentrated to -120 mL. Dimethylacetamide (270 mL) was then added to the reaction mixture and cooled to ~10C. 2,2-Dimethylpropanethioamide (1.3 g, 0.5 eq) in 2 equal portions was added to the reactor contents with stirring for ~5 minutes between additions. The reaction was warmed to 20-25 C. After 45 min, the vessel contents were heated to 75C and held for 1.75 hours . The reaction mixture was then cooled to 5C and water (270 ml) was slowly charged keeping the temperature below 30C. Ethyl acetate (4 vol) was then charged and the mixture was stirred and layers separated. Ethyl acetate (7 vol) was again charged to the aqueous layer and the contents were stirred and separated. Ethyl acetate (7 vol) was charged again to the aqueous layer and the contents were stirred and separated. The organic layers were combined and washed with water (4 vol) 4 times and stirred overnight at 20-25C. The organic layers were then concentrated under heat and vacuum to 120 mL. The vessel contents were then heated to 50C and heptanes (120 mL) were added slowly. After addition of heptanes, the vessel contents were heated to reflux then cooled to 0C and held for ~2 hrs. The solids were filtered and rinsed with heptanes (2 x 2 vol). The solid product was then dried under vacuum at 30C to obtain N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(l, l-dimethylethyl)-l,3- thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (28.8 g, 80%).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; GRESHOCK, Joel David; HOOS, Axel; WO2015/87279; (2015); A1;,
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. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-(4-Fluorophenyl)-N,N-dimethylacrylamide

General procedure: A typical procedure: Amixture of beta-dimethylaminovynil ketone 1a-h (1.0 mmol, 0.175 g), ChCl:TsOH (1:2) (0.519 g), and 3-amino-5-methylthio-1H-1,2,4-triazole 2 (1.2 mmol, 0.156 g) was heated to120 C for 5 min.Water (10 mL) was added, and the resulting product(3) was extracted with chloroform (3 × 10 mL). The organic phaseswere dried over anhydrous Na2SO4 and the solvent was evaporateduntil totally dry in order to obtain the desired triazolopyrimidines(3a-h) in a pure form. The structure of compounds 3a-h was confirmedby 1H, 13C NMR spectroscopy, determination of their melting points, gaschromatography mass spectrometry (GC-MS), high-resolution massspectra (HRMS), and, FT-IR spectra. These data are available in theSupporting Information.

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 75175-77-8.

Reference:
Article; Martins, Marcos A.P.; Paveglio, Guilherme C.; Munchen, Taiana S.; Meyer, Alexandre R.; Moreira, Dayse N.; Rodrigues, Leticia V.; Frizzo, Clarissa P.; Zanatta, Nilo; Bonacorso, Helio G.; Melo, Paola A.; Krzyzaniak, Sindy R.; Journal of Molecular Liquids; vol. 223; (2016); p. 934 – 938;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 683-57-8, name is 2-Bromoacetamide, 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 683-57-8, Quality Control of 2-Bromoacetamide

A flask was charged with 4-cyano-lH-imidazole-2-carboxylic acid (2-cyclohex-l- enyl-4-piperidin-4-yl-phenyl)-amide TFA salt (50 mg, 0.10 mmol) (as prepared in Example 14, step (b)), NEt3 (32 muL, 0.23 mmol), 2-bromoacetamide (16 mg, 0.12 mmol), and 0.5 mL of DCM and stirred for 4 h at 25 0C. The reaction was concentrated and the title compound was purified by RP-EtaPLC (C 18), eluting with 30-50 % CH3CN in 0.1 % TFA/H2O over 12 min to give 42 mg (75 %) of a white solid. 1H-NMR (400 MHz, DMSO-d6): delta 14.28 (br s, IH), 9.78 (s, IH), 9.50 (br s, IH), 8.34 (s, IH), 8.00 (s, IH), 7.88 (d, IH), 7.72 (s, IH), 7.18 (dd, IH), 7.10 (d, IH), 5.76 (m, IH), 3.94 (s, 2H), 3.58 (m, 2H), 3.12 (m, 2H), 2.80 (m, IH), 2.20 (m, 4H), 1.98 (m, 4H), 1.80 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C24H28N6O2, 433.2 (M+H), found 433.2.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl-N-(tert-butoxycarbonyloxy) carbamate (224 mg, 0.96 mmol) in DMF (2 [MNo.) ] was reacted with sodium hydride (38 mg, 0.96 mmol) at [0 C] and stirred for 20 mins at room temperature. The reaction mixture was treated by dropwise addition of benzyl [N- [4- (BROMOMETHYL)-2-FLUOROPHENYL]] carbamate compound 52 (250 mg, 0.74 mmol) and stirred for 1 hour. After concentrating, residual mixture was purified by column chromatography on Silica gel with EtOAc/hexanes (1: 5) solvent mixture as an eluant to give 355 mg of yellow oil of tert-butyl [N-[(TERT-BUTOXYVARBONYL) OXY]-N-{4-] [[(BENZYLOXY) CARBONYLAMINO]-3-FLUOROBENZYL} CARBAMATE] compound 53 (yield: [98%).] 1H-NMR [(CDC13)] 8 : 8.06 (bt, 1 H), 7.35-7. 45 (m, 5 H, Ph), 7.05-7. 12 (m, 2 H), 6.89 (bs, 1 H, NH), 5.22 (s, 2 H, [OCH2PH),] 4.68 (s, 2 H, CH2NO), 1.48 (s, 9 H, C [(CH3)] 3), 1.47 (s, 9 H, [ C (CH3) 3)]

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Digital Biotech Co., Ltd.; WO2004/35533; (2004); A1;,
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. 24167-56-4, name is 4-Fluoro-N,N-dimethylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 24167-56-4

General procedure: Oxalyl chloride (1.0 equiv) was added dropwise at r.t. (except in synthesis of 4e, where addition was at 0 C) to the corresponding N,N-dialkylbenzamide 1 (1.0 equiv) in anhydrous CH2Cl2 (1.0 mL/mmol 1) under N2 atmosphere. The reaction mixture was heated at 35 C for 5 h. Generally, a white solid was observed after few minutes. When the reaction was finished, anhydrous CH2Cl2 was added (4.0 mL/mmol 1) at 0 C; usually at this temperature the solid dissolved. A solution of trichloroacetamidine 2 (1.0 equiv) in anhydrous CH2Cl2 (1.0 mL/mmol 2) was added dropwise at 0 C. Immediately a white suspension formed, and the reaction mixture was stirred overnight at r.t. Finally, DIPEA (2.2 equiv) was added at 0 C; a pale yellow solution resulted. CH2Cl2 (20 mL) was added and the organic phase was washed with saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo. The resulting crude 1,3-diazabutadiene 4 was obtained in quantitative yield, usually contaminated with small quantities of starting material as an oil that slowly crystallized. The 1,3-diazadienes 4 were purified by flash column chromatography (silica gel, hexanes-EtOAc). After purification, 1,3-diazadienes 4 were obtained as crystals or as oils.

According to the analysis of related databases, 24167-56-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seballos-Resendiz, Arturo; Lechuga-Eduardo, Harim; Barroso-Flores, Joaquin; Martinez-Otero, Diego; Romero-Ortega, Moises; Synthesis; vol. 48; 14; (2016); p. 2205 – 2212;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 25625-57-4,Some common heterocyclic compound, 25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, molecular formula is C9H7BrF3NO, 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 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15910-91-5, name is 1-Methylcyclopropanecarboxamide, 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 15910-91-5, Formula: C5H9NO

Bromine (2. 87mol, 0. 056mol) was added to a solution of sodium hydroxide (13. 5g, 0. 338mol) in water (100ml) at 0-5 C. A slurry of 1- (1-methylcyclopropane) carboxamide (Method 51 ; 5.70g 0. 056mol) in water (sol) was then added and reaction mixture stirred at 5 C for 2 hours, then left to stand at ambient temperature for 24 hours. The mixture was then heated at 80 C for 2.5 hours, allowed to cool and mixture distilled to give the title compound (bp 75-80 C). NMR : 0.2 (q, 2H), 0.14 (q, 2H), 0.96 (s, 3H), 1.42 (s, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/76436; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 67341-01-9, 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. 67341-01-9, name is tert-Butyl (2-hydroxy-1-phenylethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-(2,6-difluoro-benzyl)-5-nitro-1H-pyrimidine-2,4-dione (82 mg, 0.29 mmol), ((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (69 mg, 0.29 mmol), and triphenylphosphine (114 mg, 0.44 mmol) were dissolved in anhydrous tetrahydrofuran (2 mL). To this solution was added diethyl azodicarboxylate (200mu?, 0.44 mmol), followed by stirring at room temperature for 4 hrs. The solution was concentrated, after which the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 3/1/1) and dried in a vacuum to afford 67 mg of the compound as a colorless oil (yield 67%). 1H NMR (300MHz, CDCl3) delta 1.30(9H, s), 3.40(1H, d), 4.50(1H, m), 5.08-5.27(4H, m), 7.02(2H, t), 7.26-7.47(6H, m), 8.78 (1H, s)

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-hydroxy-1-phenylethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sk Chemicals Co., Ltd.; EP2390250; (2011); A2;,
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. 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O2

Example No. 26Preparation of 6- ( (5- (3 , 4 -dimethoxyphenyl) -IH-pyrazolo [4 , 3 – d] pyrimidin-7-yl) amino) -2H-benzo [b] [1 , 4] oxazin-3 (4H) -one 7-chloro-5- (3 , 4 -dimethoxyphenyl) -2- (4-methoxybenzyl) -2H- pyrazolo [4 , 3-d] pyrimidine (0.16 mmol) and 6-amino-2H- benzo [b] [1 , 4] oxazin-3 (4H) -one (0.3 mmol 2 eq. , ) were suspended in eOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140°C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140°C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 418.1621 g/molHPLC-MS: analytical method Art: 2.218 min – found mass: 419 (m/z+H)

The synthetic route of 89976-75-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics