Tag: M.W=200-300

Application of 72505-21-6, 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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 18; Intermediate: 4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- carboxylic acid methyl ester; To a solution of 3-oxo-heptanoic acid methyl ester (5.0 g, 31.6 mmol) in dry dichloromethane (80 mL) add sulfurylchloride (2.82 mL). Stir the reaction mixture at room temperature for 30 minutes then add water (20 mL) and the reaction mixture extracted five times with portions of 30 mL of dichloromethane. Wash the combined organic extracts with water, saturated aqueous solution of NaHC03 and brine and then dry over MgS04. Remove the solvent under reduced pressure to give 2-chloro-3-oxo-heptanoic acid methyl ester (6.0 g), which was used in the next step without further purification. To a solution of 2-chloro-3-oxo- heptanoic acid methyl ester (6.0 g, 31.1 mmol) in ethanol (50 mL) add 4-(trifluoromethyl) thiobenzamide (6.4 g, 31.2 mmol). Heat the reaction mixture to reflux overnight. Remove the solvent under reduced pressure and purify the residue by chromatography on silica gel (eluting with a gradient of n-heptane:ethyl acetate (100:1 to 60:1)) to give 4-butyl-2-(4- trifluoromethyl-phenyl) -thiazol-5- carboxylic acid methyl ester (7.4 g) as a yellow oil. MS (ESI) m/z 344 (M+H).

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethyl)thiobenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2005/97762; (2005); A2;,
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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. 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 114790-39-5

A solution of benzyl N-(2,2-dimethoxyethyl)carbamate (50 g, 208.9 mmol) in toluene (180 mL) is treated with solid potassium hydroxide (51.6 g, 919.69 mmol) under nitrogen. After 10 minutes, benzyltriethylammonium chloride (0.8 g, 3.1 mmol) is added. After another 10 minutes a solution of allyl bromide (33 g, 272.8 mmol) in toluene (50 mL) is added drop wise over 10 minutes. The resultant mixture is stirred at 50 C for 48 hours. The mixture is cooled to room temperature and quenched with water. The organic layer is separated, washed with brine, dried over magnesium sulfate, and concentrated to dryness to give the title compound (44 g, 75%). ES/MS (m/e): 280 (M+H).

The synthetic route of 114790-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; LOSADA, Pablo Garcia; (46 pag.)WO2016/43996; (2016); A1;,
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Electric Literature of 308283-47-8, These common heterocyclic compound, 308283-47-8, name is 3-Bromo-N-(tert-butyl)benzenesulfonamide, 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.

[0190] A suspension of intermediate 34 (0.10 g, 0.29 mmol), 3-bromo-iV-2rt-butyl- benzenesulfonamide (84 mg, 0.29 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), Xantphos (20 mg, 0.035 mmol) and cesium carbonate (0.18 g, 0.55 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 “C for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue dissolved in minimum amount of EtOAc and liexanes added until solid precipitated. After filtration, the title compound was obtained as a white solid (20 mg, 12percent) .[0191] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 1.30-1.40 (m, 2H), 1.50-1.56 (m, 4H), 2.16 (s, 3H), 2.88 (t, J= 5.3 Hz, 4H), 7.17 (d, J= 7.8 Hz, IH), 7.43 (t, J= 8.0 Hz, IH), 7.59-7.60 (m, 2H), 7.58 (s, IH), 8.13 (s, IH), 7.16 (dd, J= 7.9, 1.9 Hz, IH), 8.18-8.22 (m, IH), 8.67 (s, IH), 9.37 (s, IH). MS (ES+): m/z 559 (M+H)+.

Statistics shows that 3-Bromo-N-(tert-butyl)benzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 308283-47-8.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
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Application of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
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Synthetic Route of 25893-50-9, A common heterocyclic compound, 25893-50-9, name is N-(2-Fluorophenyl)cinnamamide, molecular formula is C15H12FNO, 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: The appropriate cinnamanilide (5.0mmol), benzyl bromide (0.60mL, 5.0mmol) and KtBuO (0.55g, 5.0mmol) in THF (100mL) were stirred and heated under reflux for 1h. On cooling, the THF was removed by rotary evaporation and the residue partitioned between H2O (50mL) and EtOAc (100mL). The EtOAc was separated, washed with brine (50mL) and dried (MgSO4). Removal of the solvent gave the crude N-benzylcinnamanilide, which was either recrystallised from EtOAc/petrol, or purified by column chromatography on Al2O3, eluting with a solvent gradient from 1:1 DCM/petrol to DCM, then recrystallised as before. 4.2.10 N-Benzyl-N-(2-fluorophenyl)-3-phenylacrylamide (2k). Following the general procedure, N-(2-fluorophenyl)-3-phenylacrylamide19 1k (1.8g, 7.5mmol) was converted to 2k (2.0g, 80%) as a white solid; Rf (DCM) 0.3; mp 74-75C; deltaH (500MHz, CDCl3) 4.60 (1H, d, J 14.4Hz), 5.42 (1H, d, J 14.4Hz), 6.28 (1H, d, J 15.4Hz), 6.98 (1H, dt, J 1.5, 7.7Hz), 7.09 (1H, dt, J 0.7, 8.0Hz), 7.16 (1H, ddd, J 1.3, 7.7, 8.0Hz), 7.2-7.39 (11H, m), 7.78 (1H, d, J 15.4Hz); deltaC (CDCl3) 52.33 (CH2), 116.90 (CH, d, J 20Hz), 117.9 (CH), 124.7 (CH, d, J 4Hz), 127.5 (CH), 128.0 (CH), 128.4 (CH), 128.8 (CH), 129.0 (CH), 129.3 (C, d, J 13Hz), 129.8 (CH), 130.0 (CH, d, J 8Hz), 131.1 (CH), 135.1 (C), 137.1 (C), 143.2 (CH), 158.3 (C, d, J 250Hz), 166.2 (C); numax (solid) 1651, 1614, 1606, 1496, 1387, 1330, 1226, 1215, 1191, 1107, 1079, 980, 861, 818, 763, 733, 699, 679cm-1; m/z (EI) 331 (34, M+), 201 (38), 131 (100), 103 (36), 91 (20%); HMRS (EI) M+, found 331.1365. C22H18FNO requires 331.1367.

The synthetic route of 25893-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; King, Frank D.; Caddick, Stephen; Tetrahedron; vol. 69; 40; (2013); p. 8592 – 8601;,
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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. category: amides-buliding-blocks

A. 1-t-Butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one.

The synthetic route of 3,3-Dibromo-azepan-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4409146; (1983); A;,
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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. 25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7BrF3NO

A solution of 3-[3-(2-pyridinyl)phenyl]-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D24) (21 mg) in DMF (4ml) was cooled to 00C. Sodium hydride (2.75mg of 60% in mineral oil, 0.069mmol) was added. The solution was stirred at 00C for 45 minutes before the slow addition (1 hr) of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (19.40mg) in DMF (1 ml) using a syringe pump. The resulting solution was allowed to warm to room temperature overnight and stirred for another 18 hours. The solution was then cooled again whilst stirring to 00C and sodium hydride (2.75mg, 0.069mmol) was added. Stirring continued for 45 minutes before the slow addition (1 hr) of 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D8) (19.40mg) in DMF (1 ml) using a syringe pump. The resulting solution was allowed to warm to room temperature and stirred over the weekend, then methanol (5ml) was added and the solution was evaporated to dryness, then re-dissolved in DCM (5ml) and water (5ml) was added. The resulting solution was poured through a phase separating cartridge and evaporated to dryness Purification using mass directed auto-purification chromatography gave the title compound as a white solid (22mg). 1H NMR (CD3OD) delta: 1.39-1.51 (3H, m), 1.81-1.91 (3H, m), 1.98-2.10 (assume 4H, m), 4.39 (2H, s), 7.37-7.41 (2H, m), 7.48-7.52 (1 H, t), 7.61-7.65 (1 H, t), 7.56-7.77 (1 H, d), 7.92-7.93 (2H, m), 8.01 (1 H, s), 8.12-8.15 (2H, m), 8.48-8.50 (1 H, m), 8.63-8.97 (1 H, m), 8.98 (1 H, s). Mass Spectrum (Electrospray LC/MS): Found 507 (MH+). C28H25F3N4O2 requires 506. Ret. time 3.14 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
Amide – Wikipedia,
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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 144072-29-7 as follows. HPLC of Formula: C12H17NO3

To a solution of 31 (8.2 g, 36.7 mmol) in DCM (150 mL) were added TEA (11.1 g, 110 mmol) and MsCl (6.3 g, 55.1 mmol) at 0 C. The mixture was stirred at rt for 3 h, and quenched with water (80 mL), the aqueous layer was extracted with DCM (100 mL × 2), dried over Na2SO4, and concentrated under vacuum to yield crude 32 (7.5 g, 68%) as a yellow oil. This product was used in the following reaction without further purification

According to the analysis of related databases, 144072-29-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fujimoto, Jun; Hirayama, Takaharu; Hirata, Yasuhiro; Hikichi, Yukiko; Murai, Saomi; Hasegawa, Maki; Hasegawa, Yuka; Yonemori, Kazuko; Hata, Akito; Aoyama, Kazunobu; Cary, Douglas R.; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3018 – 3033;,
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Adding a certain compound to certain chemical reactions, such as: 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, 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 108468-00-4, HPLC of Formula: C13H20N2O2

Step 1: l-(N-boc-aminomethyl)-4-(aminomethyl) benzene (3.80g, 16.1 mmol) wasdissolved in DCM (100 mL) and DIPEA (5.0 mL, 29 mmol), followed by FmocCl (5.Og, 19 mmol)were added. The reaction mixture was stirred at room temperature for 1 hour, after which aprecipitate appeared. Water (100 mL) was added and the precipitate filtered and dried to give [4- (tert-butoxycarbonylamino-methyl)-benzyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (6.32g, 86%) as a white solid. AnalpH2_MeOH_4MIN: Rt: 3.52 mm, mlz 481.3 [M+H]

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; UNIVERSITY OF LEEDS; PHILIPPOU, Helen; FOSTER, Richard; FISHWICK, Colin; REVILL, Charlotte; YULE, Ian; TAYLOR, Roger; NAYLOR, Alan; FALLON, Philip, Spencer; CROSBY, Stuart; HOPKINS, Anna; GUETZOYAN, Lucie, Juliette; MACNAIR, Alistair, James; STEWART, Mark, Richard; WINFIELD, Natalie, Louise; (273 pag.)WO2019/186164; (2019); A1;,
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Synthetic Route of 147291-66-5, 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. 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Novabiochem 01-64-0261 commercial resin (2 g, loading : 0,94 mmol/g, 0.0018 mol) was washed with DCM (50 ml), then a solution of 3-tert- butoxycarbonylaminomethylaniline (0.009 mol ) in DCM/CH3COOH 1% (25 ml) was added and the resulting mixture was shaken for 10 minutes at room temperature. Sodium triacetoxyborohydride (0.009 mol) was added, followed by addition of DCM/CH3COOH 1% (25 ml) and the reaction mixture was shaken gently for 48 hours at room temperature. After filtration, the resin was washed 3 times with MeOH and 3 times with DCM, 3x MeOH, 3x DCM, 3x MeOH, 3x DCM, 3x MeOH, 3x DCM, 3x MeOH, 3x DCM, yielding intermediate 30, which was used in next reaction step.

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/61415; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics