Author: Jessica.F

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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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 42137-88-2 as follows. category: amides-buliding-blocks

N,N-Bis(2-chloroethyl)-p-toluenesulfonamide (171 mg, 0.576 mmol), potassium iodide (191 mg, 1.15 mmol) and K2C03 (159 mg, 1.15 mmol) were added to a stirring solution of N1- (5-chloro-4-(lH-indol-3-yl)pyrimidin-2-yl)bicyclo[3.2.1]octane-l,5-diamine_(195 mg, 0.384 mmol). The resulting mixture was then heated at 130 C for 16h. The solution was cooled to room temperature, diluted with EtOAc (100 mL) and washed with H20 three times (50 mL). The organics were combined, dried over Na2S04, filtered and evaporated to dryness. The mixture was purified by Si02 column (DCM/EtOAc 0 to 60% gradient) and afforded the title compound (133 mg, 0.182 mmol, 47%) as an off white solid.

According to the analysis of related databases, 42137-88-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; SPROTT, Kevin; MARINEAU, Jason, J.; SCHMIDT, Darby; BRADLEY, Michael; CIBLAT, Stephane; SIDDIQUI, M., Arshad; KABRO, Anzhelika; LEBLANC, Melissa; LEGER, Serge; ROY, Stephanie; WINTER, Dana, K.; MILLER, Tom; RIPKA, Amy; LI, Dansu; WO2015/154039; (2015); A2;,
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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. 27533-32-0, name is 3-Amino-2-naphthamide, A new synthetic method of this compound is introduced below., Safety of 3-Amino-2-naphthamide

To a stirred mixture of 9.3 g of 3-amino-2-naphthalenecarboxamide and 300 ml of ether was added dropwise, a solution of 8.2 g of benzoyl isothiocyanate in 100 ml of ether over 10 minutes The resulting solid was collected and crystallized from 1400 ml of hot acetonitrile, giving 11.1 g of the desired product as straw-colored crystals, mp 220-223 C.

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; American Cyanamid Company; US5001157; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 2835-68-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2835-68-9 name is 4-Aminobenzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of amine (1 mmol) in water (2 ml) was added tetrahydro-2,5-dimethoxyfuran (1.1 mmol) and gamma-Fe2O3(at)SiO2-Sb-IL (0.08 g). The reaction mixture was stirred at 100 C for a certain period of time as required to complete the reaction. During that time, the reaction was monitored constantly by TLC. After completion of the reaction, the catalyst was removed by using a magnet and washed with ethyl acetate. The aqueous solution was extracted by ethyl acetate (3 ¡Á 5 ml). The combined organic phase was dehydrated with anhydrous sodium sulfate. After the evaporation of the solvent, the residue was purified by silica gel flash chromatography using petroleum ether/ethyl acetate as the eluent to afford the pure product. 4-(1H-Pyrrol-1-yl)benzamide (3an). IR (KBr): 3142, 1645, 1613, 1577, 1525, 1475, 1425, 1394, 1327, 1199, 1120, 1064, 1014, 920, 846, 723 cm-1; 1H NMR (CDCl3, 500 MHz) delta: 6.39 (t, J = 2.0 Hz, 2H), 7.16 (t, J = 2.0 Hz, 2H), 7.47(d, J = 8.5 Hz, 2H), 7.89 (d, J = 8.5 Hz, 2H) ppm; 13C NMR (CDCl3, 125 MHz) delta: 111.4, 119.1, 119.7, 130.0, 129.1,143.4, 168.2 ppm; ESI-MS: m/z = 187 (M + 1)+; Anal. Calcd. for C11H10N2O: C, 70.95; H, 5.41; N, 15.04. Found: C, 71.12; H, 5.60; N, 14.86.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Aminobenzamide, and friends who are interested can also refer to it.

Reference:
Article; Ma, Fei-Ping; Li, Pei-He; Li, Bao-Le; Mo, Li-Ping; Liu, Ning; Kang, Hui-Jun; Liu, Ya-Nan; Zhang, Zhan-Hui; Applied Catalysis A: General; vol. 457; (2013); p. 34 – 41;,
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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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, A new synthetic method of this compound is introduced below., Computed Properties of C10H17NO2

Example 32Synthesis of cis-(6-oxa-bicyclo[3.1.0]hex-3-yl)-carbamic acid tert-butyl ester (IV-2)Solid NaHCO3 (0.0167 mol) and m-CPBA (0.0128 mol) were added in portions to a stirred solution of cyclopent-3-enyl-carbamic acid tert-butyl ester IV-1 (0.0093 mol) in CH2Cl2 (60 mL). The mixture was stirred at 0 C for the first 2 h of the reaction and then allowed to stir for about 48 h at room temperature. Aqueous 20% Na2SO3 (30 mL) was added, and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (20 mL x 3), and the combined organic layers were washed with 20% Na2SO3 (30 mL x 1), 5 % NaHCO3 (30 mL x 1), and water (30 mL x 1 ). The combined organic phase was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 100% dichloromethane) to give pure product as a colorless oil (64%).

The synthetic route of 193751-54-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (2008); A1;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 14719-21-2, 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. 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

step 1: A single jar was charged with compound dG-I (0.25 g, 0.4 mmol) Lmmo 1) and Pd (PPh3) 4 (48 mg; 0.04 mmol) were weighed into a reaction vial, Vacuum, nitrogen protection, wrapped in aluminum, add 10ml DMF, Stirring dissolved, TEA (0. 088 g; 0.8 mmol) and trifluoroacetylpropargylamine (0.2 g; 1.2 mmol) were injected, 50 C stirring 13 hours after the end of the reaction, The residue was dissolved in of ethyl acetate, Washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution, Dried over anhydrous sodium sulfate, concentrated and purified by column chromatography [V (ethyl acetate): V (n-hexane) = 1: 3] To obtain 0.1 g of a white solid, dG (AP3), in a yield of 39%

The synthetic route of 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jiao Tong University; SHEN, YUMEI; SHAO, ZHIFENG; GONG, BING; LIU, YAZHI; ZHAO, XIAODONG; JIANG, MIN; LI, XIAOWEI; TANG, DAONIAN; WU, XINYAN; (19 pag.)CN103601779; (2016); B;,
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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. 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H20N2O2

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-lH-pyrazol-l-yl)nicotinic acid (200 mg, 0.65 mmol) HATU (372 mg, 0.98 mmol), and Et3N (198 mg, 1.96 mmol) in DMF (3.0 mL) . The mixture was stirred at room temperature for 0.5 hour, then tert-butyl (3- aminopropyl)(methyl)carbamate (147.39 mg, 0.79 mmol) was added. The mixture was stirred overnight at room temperature. The reaction mixture was purified by preparative HPLC to give tert-butyl (3-(6-(4-(4-cyanophenyl)-5-hydroxy-lH-pyrazol-l- yl)nicotinamido)propyl)(methyl)carbamate (150 mg, 48%).

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Amide – Wikipedia,
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Related Products of 61903-11-5, 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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of the product of example Ii (160 mg), JV-acetylhomopiperazine (89 mg), DIPEA (370 muL) and HATU (192 mg) in dichloromethane (5 ml) was stirred at 400C for 1 h. The reaction mixture was diluted with ethyl acetate and washed with an aqueous HCl solution (0.2 M), water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [10/0 ? 8/2 (v/v)] as eluent.Yield: 230 mg; hFSHRago (CHO luc) EC50 = 5.2 nM

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, 1-(1,4-Diazepan-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. ORGANON; WO2009/98283; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics