Category: amides-buliding-blocks

Application of 16695-22-0, 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 16695-22-0 as follows.

General procedure: Reaction of compound 14 (500 mg, 0.5 mmol), diethanolamine trito-sylate15 15 (285 mg, 0.5 mmol), cesium carbonate (815 mg, 2.5 mmol), dissolved inDMF (10 mL) was done according to GP3 for 24 h at 80C. Workup and flashchromatography (toluene/ethyl acetate 3:1) gave compound 18. Yield 251 mg(42%), glass temperature 93-96C, [alpha]D20 = + 15.1 (c = 0.5, CHCl3). 1H NMR(400 MHz,CHCl3): delta = 7.63-7.06 (m, 22H, Ph), 5.03 (d ?s, 2H, J1,2 0 Hz, H-1,-1),4.55 (dd ?d, 2H, J1,2 0, J2,3 6.0 Hz, H-2,-2), 4.71 (dd, 2H, J2,3 6.0, J3,4 3.0 Hz,H-3,-3), 3.97 (m, 4H, H-4,-4, H-5,-5), 3.42-3.14 (m, 12H, H-6a,-6a, H-6b,-6b, CH2NTs, OCH2), 4.74 (d, 2H, JBn 10.5 Hz, OCHABnBn), 4.57 (d, 2H, JBn10.5 Hz, OCHABnBn), 3.68-3.80, 3.65-3.59, and 3.54-3.48 (each m, 6H, OCH2),3.04-2.96 (m, 2H, CH2NTs), 2.44, 2.37 (s, 9H, CH3Ts), 1.45 and 1.32 (s, 12H,CH3). 13C NMR (100 MHz, CHCl3): delta = 106.88 (C-1,-1), 84.80 (C-2,-2), 79.99(C-3,-3), 78.82, 77.34 (C-4,-4, C-5,-5), 73.85 (2C, OCH2Ph), 70.07, 65.96 (4C,OCH2), 50.77, 49.62, 47.89 (6C, C-6,-6, CH2NTs), 112.19 (q, 2C, Isoprop), 26.29,25.13 (4C, CH3), 21.55, 21.46 (3C, CH3Ts), 143.25-135.50, 129.60-127.25 (30C,Ph). Calcd. for C61H77N3O17S3 (1220.5): FAB-MS found [M + Na+] 1243 (75%),[M+-CH3C6H4SO2] 1064 (100%).

According to the analysis of related databases, 16695-22-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rathjens, Andreas; Thiem, Joachim; Journal of Carbohydrate Chemistry; vol. 35; 8-9; (2016); p. 397 – 411;,
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Reference of 149990-27-2,Some common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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.

To a solution of N-Boc-propargylamine (0.200 g, 1.29 mmol) in dry benzene (6.0 ml) were added Pd(PPh3)3Cl2 (18 mg, 2 mol%) and n-butylamine (2mL). The solution was frozen followed by addition of CuI (5 mg, 2 mol%). After evacuation under vacuum, the reaction mixture was purged with argon. After this degassing procedure was repeated two more times, the mixture was stirred at 45C overnight in an argon atmosphere. After the reaction mixture was evaporated under reduced pressure, the residue was taken up with dichloromethane (50 mL) and extracted with saturated aqueous sodium hydrogen carbonate (10 mL). The layers were separated and the organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel. The appropriate fractions, which were eluted with ethyl acetate-hexanes (30:70 v/v), were combined and evaporated under reduced pressure to give the trimerized product 6a as a white solid (80 mg, 40%). Homo coupling dimer 5a was also isolated as a white solid (20 mg, 10%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl but-3-yn-1-ylcarbamate, its application will become more common.

Reference:
Article; Yalagala, Ravi Shekar; Zhou, Ningzhang; Yan, Hongbin; Tetrahedron Letters; vol. 55; 11; (2014); p. 1883 – 1885;,
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154350-29-5, name is Cyclopropanesulfonamide, 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. COA of Formula: C3H7NO2S

29.8 g (246 mmol) of cyclopropanesulfonamide, 4.82 g (11.4 mmol) of tert-butyl XPhos, 1.38 g (3.77 mmol) of bis(eta3-allyl-mu-chloropalladium), and 36.6 g (265 mmol) of potassium carbonate were added sequentially to a solution of 69.3 g (189 mmol) of (1R,5S,6r)-tert-butyl 6-(3-bromophenyl)-6-ethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate, which was obtained in Reference Example 3-(b), in 400 mL of toluene with stirring under an argon stream, and the mixture was stirred at room temperature for 10 minutes, and was then stirred for 1.5 hours while heated at 110¡ã C. The obtained reaction solution was filtered through Celite, the Celite was washed with toluene, and the filtrate was concentrated under a reduced pressure. Then, 300 mL of tert-butyl methyl ether and 300 mL of a 1 N aqueous sodium hydroxide solution were added to the obtained residue to obtain an aqueous layer by liquid separation. Then, 160 mL of 2 N hydrochloric acid and 300 mL of tert-butyl methyl ether were added to the obtained aqueous layer to obtain an organic layer by liquid separation. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under a reduced pressure. Then, 200 mL of hexane and 22 mL of ethyl acetate were added to the obtained residue, and the mixture was stirred at room temperature for 30 minutes and then stirred with ice cooling for 10 minutes. The precipitated solid was collected by filtration and dried at 50¡ã C. under a reduced pressure to obtain 54.4 g of the titled compound as a white solid. (Yield 70percent) Mass spectrum (CI, m/z): 407[M++1] 1H-NMR spectrum (400 MHz, CDCl3) deltappm: 7.26 (dd, J=7.8, 7.8 Hz, 1H), 7.16 (dd, J=1.9, 1.9 Hz, 1H), 7.11-7.05 (m, 2H), 6.34 (s, 1H), 3.65 (dd, J=5.3, 11.4 Hz, 1H), 3.60 (dd, J=5.3, 11.5 Hz, 1H), 3.54 (d, J=11.4 Hz, 1H), 3.48 (d, J=11.5 Hz, 1H), 2.46 (tt, J=4.8, 8.0 Hz, 1H), 1.90 (dd, J=8.0, 5.2 Hz, 1H), 1.89 (dd, J=8.0, 5.2 Hz, 1H), 1.64-1.53 (m, 2H), 1.47 (s, 9H), 1.20-1.12 (m, 2H), 1.00-0.93 (m, 2H), 0.82 (t, J=7.4 Hz, 3H)

The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; UBE INDUSTRIES, LTD.; Iwamura, Ryo; Tsuzaki, Yasunori; Setoguchi, Hiroyuki; Akaza, Hiroto; Yamamoto, Yasuhito; Takama, Akira; Kuno, Yuka; (53 pag.)US2018/148409; (2018); A1;,
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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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

To a scintillation vial charged with the 6-bromo-4H-benzo[1,4]oxazin-3-one, Pd2(dba)3 (2.5 % substrate), 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl (6% substrate). The vial is purged under a positive flow of nitrogen and 1,4-dioxane, the amine and lithium hexamethyldisylazide (1 equivalent substrate) was added via syringe. The reaction is stirred for overnight at 90C under an atmosphere of nitrogen. Upon cooling the reaction is concentrated onto celiteunder reduced pressure and purified via flash column chromatography or by preparative LCMS.

According to the analysis of related databases, 24036-52-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/15259; (2006); A2;,
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Application of 14658-93-6, 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 14658-93-6 as follows.

General procedure: A solution of 0.04 g (0.11 mmol) of methyl 2-Z-(C-(bromomethyl)-N-tetrahydropyran-2-yloxy-carbonimidoyl)pyridine-4-carboxylate (Intermediate 12) in 0.5 mL of dry THE was added drop wise at 0C and under nitrogen atmosphere to a suspension of 0.024 g (0.13 mmol) of tert-butyl N-(2-hydroxyethyl)-N-methyl-carbamate and 0.0054 g (0.13 mmol) of NaH (60% mineral oil) in 0.5 mL of dry THE. Once the addition was complete, the reaction mixture was quenched with 5% citric acid and extracted with DCM and DCM/MeOH90:10. The combined organic layers were dried, concentrated and the crude product was purified by flash chromatography (eluent DCM:MeOH 97:3) to afford 0.022 g (27%) of 2- [(Z)-C-[2-(tert-butoxycarbonyl (methyl )am ino)ethoxymethyl]-N-tetrahydropyran-2-yloxy- carbonimidoyl]pyridine-4-carboxylic acid (Intermediate 19). MS (ESI): mlz: 436 [M-H].

According to the analysis of related databases, 14658-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IEO – ISTITUTO EUROPEO DI ONCOLOGIA S.R.L.; VARASI, Mario; VILLA, Manuela; TRIFIRO’, Paolo; FANCELLI, Daniele; MERCURIO, Ciro; VIANELLO, Paola; SARTORI, Luca; (202 pag.)WO2017/198785; (2017); A1;,
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25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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. Application In Synthesis of 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide

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.

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;,
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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. 758-96-3, name is N,N-Dimethylpropionamide, A new synthetic method of this compound is introduced below., Recommanded Product: 758-96-3

General procedure: A 50 mL Schlenk tube equipped with a stirrer bar was charged with KI (16.6 mg, 0.1 mmol), benzotriazole (59.5 mg, 0.5 mmol), DMA (2 mL), and K2S2O8 (270 mg, 1 mmol) under air. The mixture was then stirred at 80 C for 6 h (TLC monitoring), poured into H2O (20 mL), and extracted with EtOAc (3 ¡Á). Then the organic phase was evaporated under vacuum, and the crude product was purified by column chromatography [silica gel, PE-EtOAc (10:1 to 2:1)] to give a colorless oil; yield: 98 mg (96%);

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; Zhu, Zheng; Wang, Yufeng; Yang, Mingmeng; Huang, Ling; Gong, Jiuhan; Guo, Shengmei; Cai, Hu; Synlett; vol. 27; 19; (2016); p. 2705 – 2708;,
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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. 195986-74-4, name is 7-Bromo-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione, A new synthetic method of this compound is introduced below., Formula: C9H7BrN2O2

7-bromo-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (11.8 g, 46.2 mmol) was transferred to a round bottom flask. THF (0.57M) was added to the flask to make a slurry. Lithium aluminum hydride in 1M solution of THF (138.8 mmol) was added dropwise. When the addition was completed, the reaction mixture was heated to 63 C. After 19 hours, the reaction mixture was cooled to room temperature and then to 0 C. Water (3 mL) was added to the cooled reaction mixture, and the reaction mixture was stirred for 1 hour. After the 1 hour, 9 mL of 15% NaOH was added and the reaction mixture was stirred for another hour. Water was then added and the resulting precipitate was filtered off. The precipitate was then washed with ethyl acetate several times. The solvent was removed from the filtrate and the filtrate was transferred to a separatory funnel with ethyl acetate. The filtrate was extracted with ethyl acetate (3¡Á). The combined organic extracts were washed with brine (1¡Á), dried with magnesium sulfate, filtered and concentrated to give a yellow solid. Further purification (1% TEA/Ethyl acetate to start, then switched to 20% ammonia (2M solution in methanol)/ethyl acetate, then 100% methylene chloride) yielded the desired product. [0179] 1H NMR (CDCl3, 400 MHz): delta7.2(s,1H); 7.1 (dd, J=4, 8 Hz, 1H); 6.6(d, J=8 Hz, 1H); 3.8 (s, 2H); 3.0 (dt, J=8 Hz, 4H). [0180] Mass Spec: Calculated: 227.10; Found: 226.96 [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; Wyeth; US2004/9970; (2004); A1;,
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402-46-0, name is 4-Fluorobenzenesulfonamide, 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. Formula: C6H6FNO2S

Synthesis Example 6 Synthesis of N-(4-fluorophenylsulfonyl)-2-chloro-6-methoxyisonicotinamide (Compound No. 38) 1.75 g (0.01 mol) of 4-fluorobenzenesulfonamide were dissolved in 30 ml of pyridine, and added dropwise by 2.06 g (0.01 mol) of 2-chloro-6-methoxyisonicotinoyl chloride at 0 C. to 5 C., followed by agitation for 2 hrs. at room temperature. After acidified by adding aqueous hydrochloric acid, the precipitate was extracted by ethyl acetate. The organic layer obtained was dried and them concentrated to precipitate crude crystals, which were recrystallized by n-hexane/ethylacetate to 2.1 g (yield: 61.0%) of N-(4-fluorophenylsulfonyl)-2-chloro-6-methoxy isonicotinamide as white crystal.

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Kayaku Kabushiki Kaisha; US4690934; (1987); A;,
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Synthetic Route of 630-22-8,Some common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, molecular formula is C5H11NS, 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.

To a solution of 2-propen-1 -yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2- fluorophenyl}carbamate (30 g, 85.9 mmol) in DMA (300 ml_), NBS (15.3 g, 85.9 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Then 2,2-dimethylpropanethioamide (1 1 .0 g, 94.5 mmol) was added at 0 C. The mixture was stirred at room temperature for 2 h. The mixture was poured into water and extracted with EtOAc (200 ml_ x 3). The combined organic layers were washed with water and brine successively, dried over Na2SO , filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel(DCM etroleum ether 2:1 ) to afford the title compound. 1 1 g (35.4 % yield) 1 H NMR (400 MHz, CDCI3) delta ppm 8.29 (d, J=5.27 Hz, 1 H), 8.12-8.19 (m, 1 H), 7.12-7.25 (m, 2H), 6.80-6.88 (m, 2H), 5.85-5.98 (m, 1 H), 5.20-5.37 (m, 2H), 4.61 -4.67 (m, 2H). MS (ES+): 447 [M+H]+ .

The synthetic route of 630-22-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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