Amides-buliding-blocks

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(5-Amino-1-[4-(2-fluorophenoxy)-2-methylphenyl]pyrazol-4-yl}-[6-bromo-5-(2-bromoethoxy)-1H-indol-2-yl]methanone (100 mg) was suspended in acetonitrile (1.0 mL), tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (63 mg) and cesium carbonate (130 mg) were added, and the mixture was stirred at 70¡ãC for three hours. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate. After removing the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane/ethyl acetate) to give the target compound (79 mg).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; F. Hoffmann-La Roche AG; EBIIKE, Hirosato; AOKI, Toshihiro; CHIBA, Takashi; KOCHI, Masami; NAKAMA, Kimitaka; NIIZUMA, Satoshi; NISHII, Hiroki; OHWADA, Jun; SHIMAMURA, Hiroyuki; SUGE, Aiko; NAKANISHI, Yoshito; KOBAYASHI, Natsuki; (594 pag.)EP3312172; (2018); A1;,
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A common heterocyclic compound, 88-96-0, name is Phthalamide, molecular formula is C8H8N2O2, 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. 88-96-0.

Example 20B (404 mg, 1.13 mmol), triphenylphosphine (455 mg, 1.6 eq.) and phthalamide (222 mg, 1.4 eq.) were mixed in 3.5 mL of toluene. Then, di-tert-butylazodicarboxylate (DBAD, 398 mg, 1.6 eq.) was added. The reaction flask was flushed with argon and then heated to 90 C. After stirring overnight at 90 C., the mixture was cooled to room temperature, concentrated and the resulting oil was purified by column chromatography (eluding with 20% to 40% ethyl acetate in hexane) to give the title compound (684 mg).

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

Reference:
Patent; Pei, Zhonghua; Geldern, Thomas von; Madar, David J.; Li, Xiaofeng; Basha, Fatima; Yong, Hong; Longenecker, Kenton L.; Backes, Bradley J.; Judd, Andrew S.; Mulhern, Matthew M.; Stewart, Kent D.; US2007/49596; (2007); A1;,
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191170-76-0, The chemical industry reduces the impact on the environment during synthesis 191170-76-0, name is Benzyl 4-bromophenethylcarbamate, I believe this compound will play a more active role in future production and life.

A solution of H2SO4 (3 ml) and AcOH (6 mL) was cooled in an ice bath for 10 min. Paraformaldehyde (1.00 g, 33.3 mmol) and benzyl (4-bromophenethyl)carbamate (0.92 g, 2.75 mmol) were added to the cooled solution and the reaction was stirred for 10 min at 0 C, where upon the reaction was poured onto ice (ca. 50 g). When the ice melted, the aqueous solution was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCCb (1 x 50 mL), water (1 x 50 mL), and brine (1 x 50 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure. The crude material was purified via flash column chromatography eluting with EtOAc:hexanes (5:95) to give 720 mg (76%) of title co s consistent with literature.1

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

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARTIN, Stephen, F.; SAHN, James, J.; LINKENS, Kathryn, Taylor; (119 pag.)WO2017/190109; (2017); A1;,
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89979-12-4, 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 89979-12-4 as follows.

Example 12 Preparation of Intermediate 11 [0467] [0468] HATU (1.37 g, 3.59 mmol) was added to a solution of 5-chloro-2-(methylsulfonamido)benzoic acid (823 mg, 3.29 mmol) in DMF (15.0 mL), and the reaction mixture was stirred at room temperature. After 1 h, a solution of crude intermediate 6 (220 mg, 2.99 mmol) in DMF (1 mL) was added followed by the addition of triethylamine (2.00 mL, 14.3 mmol), and the reaction mixture was stirred at room temperature for 19 h. The reaction mixture was partitioned between ethyl acetate (250 mL) and saturated aqueous sodium bicarbonate solution (200 mL), and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution (200 mL) and saturated sodium chloride solution (200 mL), was dried over Na2SO4, and was concentrated under reduced pressure. The crude residue was purified via SiO2 column chromatography (12 g SiO2 Combiflash HP Gold Column, 0-100% ethyl acetate/hexanes) to afford intermediate 11 (736.2 mg, 51% (2-steps)) as a white solid. [0469] 1H NMR (CDCl3, 400 MHz): delta 10.05 (br s, 0.2H), 9.13 (br s, 1H), 8.95 (br s, 1H), 8.81 (br s, 0.2H), 7.70 (d, J=8.8 Hz, 1H), 7.56 (d, J=8.8 Hz, 0.2H), 7.40 (dd, J=8.8, 2.4 Hz, 1H), 7.33 (d, J=2.4 Hz, 1H), 7.31 (d, J=4.4 Hz, 0.2H), 6.45 (s, 1H), 6.40 (br s, 0.2H), 6.28 (br d, J=4.4 Hz, 1H), 5.01 (br s, 0.2H), 4.54 (br d, J=14.0 Hz, 0.2H), 3.35 (br d, J=13.2 Hz, 1H), 3.15-3.03 (m, 1H), 2.92 (s, 3H), 2.39 (s, 3H), 2.13-1.98 (m, 1H), 1.90-1.59 (m, 2H), 1.59-1.31 (m, 3H). [0470] 13C NMR (CDCl3, 100 MHz): delta 167.09, 156.12, 153.13, 147.86, 135.68, 131.79, 131.66, 131.38, 130.12, 125.91, 125.44, 117.08, 93.74, 47.65, 44.07, 39.81, 27.83, 25.47, 19.78, 16.90. [0471] LCMS (ESI) m/z 482.1 [M+H]+, tR=2.79 min. [0472] HPLC tR (min), purity %: 5.438, 99% [0473] Rf=0.47 (50% EtOAc/hexanes). [0474] Chiral HPLC, 99% ee (Chiralpak IC 5 mM, 4.6¡Á150 mm, 10-95% MeCN/H2O, 0.05% trifluoroacetic acid modifier) (S)-isomer tR=29.739 min, (R)-isomer tR=29.495 min.

According to the analysis of related databases, 5-Chloro-2-(methylsulfonamido)benzoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Siegel, Dustin; Sperandio, David; Yang, Hai; Sangi, Michael; Parrish, Jay P.; Hui, Hon Chung; US2013/273037; (2013); A1;,
Amide – Wikipedia,
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749927-69-3, Adding a certain compound to certain chemical reactions, such as: 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, 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 749927-69-3.

100 ml of DMF was added to a 250 ml three-necked flask,A solution of 18.5 g of 5,5-dimethyl-3- (3-trifluoromethyl-4-fluorophenyl) -2-thiamidazol-4-one was successively added with stirring,Ice bath cooling to 0-5 C,Add 3.9 g of sodium hydride in portions.Plus,The ice bath continues to stir for 30 min.13.68 g of 2-fluoro-4-bromobenzoylmethylamine was dissolved in 30 ml of DMF,Slowly add it toIn the reaction solution, control the internal temperature 0-5 C.Plus finished, returned to room temperature, continue to stir 5h,TLC monitoring reaction is completed.The reaction solution was addedTo 500 ml of water, filtered to obtain crude.After drying, column chromatography was performed to obtain 23.9 g of enterine, the yield was 87.3%.

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, 4-Bromo-2-fluoro-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Yinuo Dabo Pharmaceutical Technology Co., Ltd.; Fu Qingquan; Yue Lijian; Lin Qiang; Liao Xianbo; Zhao Maoxian; Qin Yan; (8 pag.)CN104844520; (2017); B;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., 121492-06-6

General procedure: 5-Amino-(30-[N0-methyl-N0-tert-butoxycarbonyl]propyl)-3-(N,N-dimethylcarbox-amide)-6-nitrochromane (9a).[29]A mixture of 5-chloro-3-N,N-dimethyl-carboxamide-6-nitro-chromane (8) (300 mg, 1.10 mmol), primary amine N-Boc-N-methyl-1,3-trimethylenediamine (18) (5.50 mmol),and N-methyl-pyrrolidinone (1.0 mL) was heated in a sealedtube at 758C for 48 h. The reaction mixture was poured into amixture of diethyl ether and water (1 : 1, 80 mL) and the mixturestirred for 30 min. The mixture was transferred to a separationfunnel and the ether layer washed with water (4 25 mL). Theorganic phase was dried over anhydrous sodium sulfate, filtered,and evaporated under reduced pressure. The crude product waspurified by flash chromatography (silica gel, 5 % methanol indichloromethane). The product 9a[29]was isolated as a brightyellow oil (381 mg, 87 %).

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:
Article; Schmit, David; Milewicz, Urszula; Boerneke, Mark A.; Burley, Scott; Walsworth, Kevin; Um, Joann; Hecht, David; Hermann, Thomas; Bergdahl, B. Mikael; Australian Journal of Chemistry; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6083-47-2, name is 4-(Dimethylamino)benzamide, 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 6083-47-2, 6083-47-2

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

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, 4-(Dimethylamino)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Amide – Wikipedia,
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Some common heterocyclic compound, 142-26-7, name is N-Acetylethanolamine, molecular formula is C4H9NO2, 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. 142-26-7

To a solution of 3-((4-carbamoyl-2,6-difluorophenoxy)methyl)-4-chlorobenzo[ib]thiophene-2- carboxylic acid 69 (150 mg, 0.38 mmol) in DMF (8 ml.) was added N-( 2- hydroxyethyl)acetamide (78 mg, 0.76 mmol), EDCI -HCI (146 mg, 0.76 mmol) and DMAP (10 mg, 0.076 mmol) and the mixture was stirred at room temperature for 4 h. Water (150 ml.) was added and the mixture was extracted with EtOAc (100 ml. x 3). The combined organic extracts were washed with water (3 x 150 ml_), brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH = 1 :0 to 100:1 ) to give the title compound (60 mg, 73%) as a white solid. LCMS-C: rt 2.22 min; m/z 482.9 [M+H]+, 504.9 [M+Na]+. 1H NMR (400 MHz, DMSO-de) d 8.14 (dd, J = 7.9, 1.2 Hz, 1 H), 8.06 – 8.00 (m, 2H), 7.66 – 7.53 (m, 5H), 6.13 (s, 2H), 4.22 (t, J = 5.6 Hz, 2H), 3.35 (t, J = 5.6 Hz, 2H), 1.80 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 142-26-7, its application will become more common.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin, Joseph; CAMERINO, Michelle, Ang; WALKER, Scott, Raymond; STEVENSON, Graeme, Irvine; STUPPLE, Paul, Anthony; (266 pag.)WO2019/219820; (2019); A1;,
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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,
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25408-61-1, A common heterocyclic compound, 25408-61-1, name is 2,2-Dimethoxy-N,N-dimethylacetamide, molecular formula is C6H13NO3, 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.

[0184] Combine 1-methyl-2-nitro-4-trifluoromethoxybenzene (3.73 g, 16.86 mmol), pyrrolidine (1.32 g, 18.55 mmol),N,N-dimethylformamide dimethyl acetal (6.03 g, 50.58 mmol), and dry DMF (35 ml). Heat to about 105. After 19 hours,remove the DMF under reduced pressure to give an oily residue. Combine the residue and ethyl acetate, wash withbrine, dry (Na2SO4), then concentrate to give N,N-dimethyl-2-(2-nitro-4-trifluoromethoxyphenyl)vinylamine.

The synthetic route of 25408-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; Chen, Zhaogen; Cohen, Michael Philip; Fisher, Matthew Joseph; Gillig, James Ronald; McCowan, Jefferson Ray; Miller, Shawn Christopher; Schaus, John Mehnert; Giethlen, Bruno; (141 pag.)EP1859798; (2015); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics