Tag: M.W=100-200

Related Products of 63920-73-0, A common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 20. Preparation of 2-[4-(2-hydroxy-ethoxy)-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one [0239] To a flask (250 mL) with a magnetic stirrer were added 4-hydroxybenzalde (10.0 g, 81.8 mmol), 2-chloroethanol (26.3 g, 327 mmol), potassium carbonate (22.6 g, 163 mmol), and ethanol (80 mL). The reaction mixture was stirred at 700C for 16 hours. Potassium carbonate was filtered and ethanol was removed. The residue was diluted with ethyl acetate (200 ml_) and washed with 5% sodium hydroxide (100 ml_), water (100 ml_), and brine (100 ml_). The crude product was purified by column chromatography (silica gel, 230-400 mesh), using hexane / ethyl acetate (1 :1) as eluent, to afford 4-(2-hydroxy-ethoxy)-benzaldehyde. Yield: 10.0 g (73%).[0240] To a solution of 2-amino-4,6-dimethoxy-benzamide (0.400 g, 2.00 mmol) and 4-(2-hydroxy-ethoxy)-benzaldehyde (0.340 g, 2.00 mmol) in N, N- dimethylacetamide (8 ml_) were added NaHSO3 (0.390 g, 2.20 mmol) and p-TSA (38 mg, 0.20 mmol). The reaction mixture was stirred at 115-1200C for 5 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was diluted with water (40 ml_) and the solid was collected, mixed with methanol (50 ml_), and stirred for 30 min. The solid was filtered and rinsed with ether (30 ml_) to give the title compound as white solid. Yield: 0.42 g (61%). 1H NMR (400 Hz, DMSO-d6): delta 11.98 (s, 1H), 8.18 (d, 2H), 7.08 (d, 2H), 6.78 (s, 1 H), 6.52 (s, 1H), 4.98 (s, 1 H), 4.10 (t, 2H), 3.90 (s, 3H), 3.84 (s, 3H)1 3.74 (t, 2H). MS (ES+) m/z: 343.13 (M+1).

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); 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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl methylcarbamate

A solution of aniline (0.911 mL, 10.0 mmol) and di-tert-butyl dicarbonate (2.34 mL, 10.2 mmol) in THF(5.0 mL) was stirred for 1 h at room temperature. The resulting mixture was concentrated to obtain N-tert-butoxycarbonylaniline(10) (2.03 g, quant.) as colorless crystals. The crude product was used without purification. (Step 2) A solution of 10 (545 mg, 2.82 mmol) and (Z)-1-bromo-4-methoxybut-2-ene (11) (422 mg,2.56 mmol) in DMF (8.5 mL) was treated with sodium hydride (60 wt.% in oil, 154 mg, 3.85 mmol) at 0 C. The resulting mixture was stirred for 1 h at 50 C and quenched with saturated aqueous ammonium chloride at 0 C.Extractive workup and purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 5/1 asthe eluent) afforded (Z)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate (12) (654 mg, 92% yield) as acolorless oil. (Step 3) A solution of diisopropylamine (484 L, 3.45 mmol) in THF (4.2 mL) was treated with a1.6 M n-butyllithium hexane solution (2.30 mL, 3.7 mmol) at 0 C under an argon atmosphere and the mixture was stirred for 30 min at the same temperature. A solution of 12 (649 mg, 2.34 mmol) in THF (7.5 mL) was added to the solution at 0 C and the mixture was stirred for 3 h at the same temperature. The resulting mixturewas quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified bychromatography on silica gel (hexane/ethyl acetate = 20/1 as the eluent) to give 2f (516 mg, 90% yield)

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:
Article; Tayama, Eiji; Horikawa, Kouki; Iwamoto, Hajime; Hasegawa, Eietsu; Tetrahedron Letters; vol. 55; 19; (2014); p. 3041 – 3044;,
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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. 198967-24-7, name is 2-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H10FNO2

Example 48: 4-tert-Butyl-N-[5-chloro-2-(2-fluoro-benzoyi)-pyridin-3-yl]- benzenesulfonamide; [00439] N-(2-Bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl- benzenesulfonamide (140 mg, 300 mmol) was placed in a dry 2-neck 10 mL round-bottom flask. The flask was evacuated and purged with nitrogen, followed by the addition of THF (1 mL). The homogeneous mixture was lowered to -5 C and /PrMgCI (0.33 mL, 2.0 M) was added dropwise. Upon completion of the addition, the reaction was stirred 90 minutes, followed by the slow addition of 2- fluoro-N-methoxy-N-methyl-benzamide (140 mg, 750 mmol). The reaction was stirred overnight, during which the ice-bath warmed to room temperature. The following day, the reaction was quenched with a small quantity of MeOH and the solvents evaporated in vacuo. The residue was subsequently treated with 4.0 M HCI (in dioxane) (1 mL, 4.0 mmol) and H2O (0.33 mL), and then stirred at 80 C for two hours. The resultant solution was diluted with EtOAc, washed with water, saturated sodium bicarbonate, and brine; dried with MgSO4, and evaporated employing reduced pressure. The crude sulfonamide was finally purified via preparatory TLC (20% EtOAc/hexanes) and recrystallization from MeCN/H2O to afford 98 mg of the title compound: 1H NMR (400 MHz, CDCI3) delta 10.6 (s, 1 H), 8.3 (d, 1H), 8.2 (d, 1H), 7.74 (d, 2H), 7.6 (d, 1 H), 7.5 (d, 1 H), 7.43 (d, 2H), 7.42-7.37 (m, 2H), 1.26 (s, 9H); MS (ES) M+H expect 447.1 , found 447.5.

According to the analysis of related databases, 198967-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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Application of 4815-28-5, The chemical industry reduces the impact on the environment during synthesis 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-amino-4, 5, 6, 7-tetrahydrobenzo[b]thiophene-3-carboxamide 1b (1.0 mmol), ketones 2 (1.0 mmol) and InCl3 (10%, w/w) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table. After completion of the reaction (indicated by TLC) the reaction mixture was filtered to remove the insoluble catalyst and wash with acetonitrile (2 X 5mL). The filtrate was collected and concentrated under vacuum. The solid isolated was triturated in MTBE (10 mL), filtered and dried to give the desired product.

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-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ismail; Kuthati, Bhaskar; Thalari, Gangadhar; Bommarapu, Venkatesham; Mulakayala, Chaitanya; Chitta, Suresh Kumar; Mulakayala, Naveen; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1446 – 1450;,
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Some common heterocyclic compound, 1882-71-9, name is 2-Amino-5-methoxybenzamide, molecular formula is C8H10N2O2, 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. SDS of cas: 1882-71-9

General procedure: 2-aminobenzamide (1, 1.0 mmol), 1,3-diketone (2, 1.5 mmol), Yb(OTf)3 (0.050 mmol, 5.0 molpercent),and mesitylene (2.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 60°C (bath temp.) for 24 h with stirring. The reaction mixture was then cooled to room temperature and analyzed by GLCand GC-MS. The product 3 was isolated by medium-pressure column chromatography on silica gel(eluent: EtOAc/hexane = 30/70 ~ EtOAc 100percent. For 3j, eluent: MeOH/CHCl3 = 30/70 ~ 50/50) andrecrystallization from MeOH/hexane. The products 3l and 3m were isolated by recrystallizationfrom EtOAc/hexane. 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6 (For 3j, in a mixture of DMSO-d6 and methanol-d4). Elemental analyses were performed at the Microanalytical Center of Kyoto University. The analytical and spectral data of 3a,10 3b-c,11 3d,12 3e,13 3f,14 3g-h,10 and 3j-l,7 are fully consistent with those reported previously. The products 3i,15 and 3m16 were characterized below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1882-71-9, its application will become more common.

Reference:
Article; Yoshimura, Tsutomu; Naito, Shun-Ichi; Yuanjun, Di; Son, Aoi; Kimura, Yu; Toshimitsu, Akio; Kondo, Teruyuki; Heterocycles; vol. 93; 2; (2016); p. 816 – 823;,
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Application of 147356-78-3, These common heterocyclic compound, 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, 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.

Isopropylmagnesium chloride (2.0 M in THF, 2.4 mL, 4.76 mmol) was added dropwise to a solution of a 2:1 mixture of (5S,7R)-2-bromo-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazol-7-ol and (5S,7R)-2-bromo-7-fluoro-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazole (0.470 g) and N- methoxy-N-methylcyclopropanecarboxamide (0.634 g, 4.76 mmol) in THF (15.9 mL) at 0C over 15 min. After lh, saturated aqueous ammonium chloride was added. The aqueous layer was extracted with isopropyl acetate (2 x 20 mL). The combined organic layers were dried over sodium sulfate, concentrated and the crude residue was purified by prep HPLC/SFC to afford arbitrarily assigned cyclopropyl((5S,7R)-7-fluoro-5-(o olyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l ,2,4]triazol-2-yl)methanone (137 mg, 0.480 mmol) and cyclopropyl((5S,7R)-7-hydroxy-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazol-2-yl)methanone (33.8 mg, 0.119 mmol). cyclopropyl((5S,7R)-7-fluoro-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l ,2,4]triazol-2- yl)methanone: NMR (400 MHz, DMSO-i) delta 7.33 – 7.14 (m, 3H), 6.89 (d, J= 7.5 Hz, 1H), 6.35 (ddd, J = 56.2, 6.8, 1.6 Hz, 1H), 6.19 (td, J = 6.9, 3.2 Hz, 1H), 3.59 – 3.27 (m, 1H), 3.11 – 2.91 (m, 2H), 2.38 (s, 3H), 1.14 – 1.01 (m, 4H). LCMS RT = 4.81 min, m/z = 286.1 [M + H]+. Prep SFC Information: Column: Torus Diol 5 muiotaeta, (150 x 30 mm), Mobile Phase: Carbon Dioxide (A) / 0.1 % Ammonium Hydroxide in Methanol (B), Elution Program Isocratic: 5% B Flow Rate: 150 mL/min, Column Temperature: 25 C, Wavelength: 220 nm cyclopropyl((5S,7R)-7-hydroxy-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazol-2- yl)methanone: NMR (400 MHz, DMSO-d6) delta 7.30 – 7.13 (m, 3H), 7.01 – 6.94 (m, 1H), 6.25 (bs, 1H), 5.75 (dd, J = 8.1, 5.8 Hz, 1H), 5.23 (dd, J = 7.9, 4.6 Hz, 1H), 3.63 – 3.52 (m, 1H), 3.03 – 2.92 (m, 1H), 2.38 (s, 3H), 2.31 – 2.14 (m, 1H), 1.09 – 0.96 (m, 4H). LCMS RT = 4.08 min, m/z = 284.1 [M + H]+. Prep HPLC Information: Column: Gemini-NX CI 8, 5muiotaeta (50 x 30 mm), Mobile Phase: 0.1 % Ammonium Hydroxide in Water (A) / Acetonitrile (B), Elution Program Gradient: 10% to 60%> B Flow Rate: 60 mL/min, Column Temperature: 25 C, Wavelength: 254 nm

The synthetic route of 147356-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); 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. 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., name: 6-Amino-2H-1,4-benzoxazin-3(4H)-one

A solution of 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 6.49 g, 39.5 mmol) and (2R)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (first eluting compound in step 18.i, 8.0 g, 39.5 mmol) in 9-1 EtOH/H2O (240 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure. Residual starting aniline could be removed by addition of Et2O/MeOH followed by filtration. The filtrate containing the product was concentrated under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4) to afford the title intermediate as a brown oil (5.82 g, 40percent yield).MS (ESI, m/z): 367.3 [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; ACTELION PHARMACEUTICALS LTD.; US2011/195949; (2011); A1;,
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Electric Literature of 5511-18-2, These common heterocyclic compound, 5511-18-2, name is Adamantane-1-carboxamide, 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.

Powdered LiAlH4 (3 g, 80 mmol) was added to a stirred solution of the carboxamide in THF (120 mL) at 0 C. After warming to ambient temperature, the suspension was heated at reflux for 16 h, cooled, and saturated aqueous sodium hydroxide (20 mL) was added dropwise at 0 C with vigorous stirring. After stirring for 1 h at ambient temperature, the mixture was filtered and the residue was washed with CH2Cl2 (60 mL). The combined organic portions were dried (MgSO4) and evaporated in vacuo to give the crude amine S8 (4.1 g, 60% over 3 steps) as a colourless oil with some solid impurities. The crude was then purified by flash chromatography on silica eluting with CH2Cl2-MeOH-NH4OH (90:9:1) to give the pure amine S8 as a colourless oil; deltaH (200 MHz; CDCl3) 2.31 (2 H, s), 1.98 (3 H, br s), 1.76-1.60 (6 H, m), 1.46-1.45 (6 H, m). The spectroscopic data matched that reported by the Aldrich Library.

Statistics shows that Adamantane-1-carboxamide is playing an increasingly important role. we look forward to future research findings about 5511-18-2.

Reference:
Article; Beinat, Corinne; Banister, Samuel D.; Hoban, Jane; Tsanaktsidis, John; Metaxas, Athanasios; Windhorst, Albert D.; Kassiou, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 828 – 830;,
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Related Products of 16982-21-1, 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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of ethyl thiooxamate (0.40 g, 3.0 mmol) and 2-Bromoacetophenone (0.60 g, 3.0 mmol) in ethanol (20 ml) was heated to reflux for 6 h. The reaction mixture was concentrated in vacuo, then diluted with ethyl acetate (30 ml), and washed with 1N NaHCO3 (3 × 20 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product (0.52 g, 74%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta: 8.55 (s, 1H), 8.08, 8.06 (dd, J = 1.7, 7.6 Hz, 2H), 7.52-7.39 (m, 3H), 4.42 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H).

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

Reference:
Article; Xu, Xue; Deng, Liming; Nie, Lu; Chen, Yueming; Liu, Yanzhi; Xie, Rongrong; Li, Zheng; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 525 – 528;,
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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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jackson, James E.; O’Brien, Brittany N.; Kedzior, Sonya K.; Fryz, Gage R.; Jalloh, Fatmata S.; Banisafar, Arash; Caldwell, Michael A.; Braun, Max B.; Dunyak, Bryan M.; Dye, James L.; Tetrahedron Letters; vol. 56; 45; (2015); p. 6227 – 6230;,
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