Month: August 2021

Reference of 326-67-0,Some common heterocyclic compound, 326-67-0, name is N-(2-Fluoro-4-methylphenyl)acetamide, molecular formula is C9H10FNO, 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 546 g (3.27 mol) of crude 2-fluoro-4-methyl-acetanilide was added chlorosul- phonic acid (2000 g, 17.24 mol) with stirring at a temperature below 70C. Stirring was continued for 3 hours at a temperature of 70C. The reaction mixture was poured onto ice and then extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to yield the title compound (500 g, 57.8%). H NMR (400 MHz, CDCI3): delta = 9.1 (d, 1 H, J = 7.2 Hz), 7.39-7.52 (m, 1 H), 7.14 (d, 1 H, J = 1 1 .2 Hz), 2.72-2.78 (m, 3H), 2.2-2.3 (m, 3H).

The synthetic route of 326-67-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KAISER, Florian; GROss, Steffen; LANGEWALD, Juergen; NARINE, Arun; WO2013/30262; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 201162-53-0,Some common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, molecular formula is C11H20N2O2, 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.

3,8-diazabicyclo [3.2.1] octane-3-carboxylic acid tert-butyl ester (320 mg, 1.5 mmol)And bromoethane (817 mg, 7.5 mmol)Was dissolved in acetonitrile (50 mL), potassium carbonate (1.03 mg, 7.5 mmol) was added and reacted at 40 C for 16 hours.The organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound which was extracted with ethyl acetate (50 mL) The title compound was obtained as a color oil (350 mg, yield 97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Boc-3,8-Diazabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (tert-butoxycarbonyl)oxycarbamate

Example 17: 7¾ -butyl i2-fl2-amino-3-chloro-6,7,10,ll-tetrahydro-7,ll- methano cvcloocta[bl uinolin-9-yl)ethyll (tert- butox carbonvDoxyl carbamate (HUP 16)A solution of tert-butyl-N-(tert-butoxycarbonyl)-carbamate (140 mg, 0.6 mmol) in anhydrous DMF (1.3 mL) was treated with sodium hydride (60% in oil, 26 mg, 0.65 mmol). The reaction mixture was stirred 40 min at r.t. and treated with a solution of mesylate (HUP 13) (157 mg, 0.4 mmol) in anhydrous DMF (2 mL). The reaction mixture was stirred at r.t. for 120 h, then at 60 C for 5 h. The mixture was then diluted with water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic layers were washed with brine (50 mL), then water (50 mL), dried with Na2S04 and concentrated under reduced pressure to afford a yellow solid (313 mg). Purification by flash chromatography (AcOEt / MeOH 10/0 to 8/2, v/v) afforded the desired Huprine (HUP 16) as a white solid (98 mg, 46%).Rf (AcOEt / MeOH 8/2, v/v) = 0.50.m.p. = 114C (decomposition).1H NMR (300 MHz, CDC13): delta = 1.41 (s, 9H, N-Boc or O-Boc), 1.46 (s, 9H, N- Boc or O-Boc), 1.84-2.02 (m, 3H, Hio, ¾), 2.10-2.22 (m, 2H, Hi4), 2.52 (dd, J = 17.1 Hz, J = 3.4 Hz, 1H, ¾), 2.67-2.71 (m, 1H, H7), 2.89 (d, J = 17.5 Hz, 1H, H6), 3.06 (dd, J = 17.6 Hz, J = 5.6 Hz, 1H, H6), 3.14-3.18 (m, 1H, Hn), 3.66-3.88 (m, 2H, His), 5.03 (brs, 2H, NH2), 5.56 (d, J = 5.1 Hz, 1H, H8), 7.21 (dd, J = 9.0 Hz, J= 1.9 Hz, 1H, H2), 7.67 (d, J= 9.0 Hz, 1H, ¾), 7.77 (d, J= 1.9 Hz, 1H, H4). 13C NMR (75 MHz, CDC13): delta = 27.4 (Cn), 27.6 (N-Boc or O-Boc), 28.1 (N-Boc or O-Boc), 28.2 (C7), 28.9 (C10), 33.8 (C13), 34.8 (Ci4), 39.4 (C6), 68.1 (Ci5), 82.3 (C-Me3 of N-Boc), 84.9 (C-Me3 of O-Boc), 115.1 (Cna or Ci2a), 115.8 (Cna or Ciza), 122.0 (Ci), 124.6 (C2), 126.9 (C4), 127.0 (C8), 132.9 (C3), 134.6 (C9), 146.5 (C4a or Ci2), 147.0 (C4a or C12), 152.2 (C=0 of N-Boc), 154.8 (C=0 of O-Boc), 158.3 (C5a).MS (ESI+): m/z (%): 530.20 (100) [M+H]+, 532.20 (39).ICso rh-AC E : 14.8 +/- 3.2 nM.ICso r/i-BuChE : 421 +/- 72 nM.

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; UNIVERSITE DE ROUEN; RONCO, Cyril; RENARD, Pierre Yves; JEAN, Ludovic; NACHON, Florian; ROMIEU, Anthony; WO2011/124712; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4424-80-0

To a mixture of 4,5-dihydro-lH-benzo[b]azepin-2(3H)-one (10.6 g, 65.8 mmol) in DCM (150 mL) cooled in an ice/water bath was added TMEDA (29.8 mL, 197 mmol), then dropwise over 20 minutes was added TMSI (26.9 mL, 197 mmol). The mixture was stirred cooled for 60 minutes, iodine (25.03 g, 99 mmol) was added and the mixture was stirred cooled for another 60 minutes. The reaction was quenched with 5% Na2S2C”3 and stirred 15 minutes. The resulting solid was filtered and dried to give 11.3 g tan solid. Layers of filtrate were separated. Organics were concentrated to a solid, triturated in diethyl ether and solid was filtered and dried to give 5.52 g light brown solid (87% yield, both batches). 1H MR (DMSO-de) delta: 9.93 (s, 1H), 7.22 – 7.30 (m, 2H), 7.09 – 7.17 (m, 1H), 6.99 (d, J = 7.3 Hz, 1H), 4.63 (dd, J = 9.1, 6.8 Hz, 1H), 2.52 – 2.81 (m, 4H); MS (m/z) 288.0 (M+H+).

The synthetic route of 4424-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 609-66-5, 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 609-66-5 as follows.

General procedure: An oven-dried Schlenk tube was charged with benzamide 1 (0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and aryl iodide 2 (1.0 mol). The tube was evacuated and backfilled with N2 (3 ×), and then DMEDA (0.2 mmol) and anhyd toluene (5.0 mL) were added. The reaction mixture was stirred at 110 C for 48 h. H2O was added and the crude product was extracted with EtOAc. The combined organic phases were washed with brine and H2O, dried (Na2SO4), and concentrated under reduced pressure. The product was purified by silica gel chromatographyto give the desired N-arylated benzamides (Table 2).

According to the analysis of related databases, 609-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Fei; Wu, San; Hu, Weiye; Zhang, Songlin; Synthesis; vol. 50; 5; (2018); p. 1090 – 1096;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 563-83-7, name is Isobutyramide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Isobutyramide

A solution containing isobutyramide (10 g, 115 mmol) in THF (250 mL) was treated with phosphorous pentasulfide (4.1 g, 9.22 mmol), stirred at 25 C. for 64 hours, concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (8.6 g, 73% yield), which was used without further purification.

The synthetic route of 563-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
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 125414-41-7 as follows. HPLC of Formula: C8H17NO4

The suspension of powdered KOH (3.05 g) and anhydrous THF (15 mL) was cooled to 0 C, Ar protection. Compound 2 (2.06 g) was dissolved in dry THF (10 mL) Was added dropwise to the reaction solution, After adding 0 reaction 15min, A solution of 4.7 mL of bromopropyne was added dropwise, 0 reaction 5min after the temperature to 35 C overnight, Deionized water (100 mL) was added, CH2Cl2 extraction, Saturated brine washing, Anhydrous Na2SO4 dried, filter, concentrate, Column separation, A yellow liquid 3 (2.467 g, 88%) was obtained.

According to the analysis of related databases, 125414-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangxi University; Wang, Mian; Wang, Jianyi; Chen, Zhengjun; (18 pag.)CN106554378; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 811442-84-9, name is tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

General Procedure XX. PEG Monomethacrylates. Preparation of Compound 43-1 To a solution of mono-Boc-protected PEG4 diamine (1.0 g, 2.97 mmol) in chloroform (30 mL), methacrylic anhydride (0.55 mL, 3.46 mmol) and triethylamine (0.55 mL, 3.95 mmol) were successively added, and the reaction mixture was stirred at room temperature overnight. Then the reaction mixture was concentrated under reduced pressure and the residue was taken up into EtOAc (40 mL). The solution was washed with 1 N HCl (2*40 mL), saturated NaHCO3 (40 mL), and brine (40 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by reversed phase flash chromatography (C18 SiO2, eluted with gradient of MeOH in water+0.05% TFA) affording the desired intermediate (553 mg, 46% yield) as a colorless oil. The purified oil (553 mg, 1.37 mmol) was dissolved in DCM (5 mL) and treated with TFA (1 mL) for 3 h at room temperature, and then the reaction mixture was concentrated under reduced pressure. The residue was dried under high vacuum yielding desired PEG4-mono-methacrylamide 43-1 (750 mg, quant., TFA salt) as amber oil.

The synthetic route of 811442-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Profusa, Inc.; GAMSEY, Soya; BERNAT, Viachaslau; KUTYAVIN, Alex; CLARY, Jacob William; PRADHAN, Sulolit; (192 pag.)US2018/179233; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, 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 104060-23-3, Safety of N-Boc-2-(4-Aminophenyl)ethanol

To a solution of tert-butyl (4-(2-hydroxyethyl)phenyl)carbamate (6.90 g, 30 mmol) and imidazole (2.45 g, 36 mmol) in DCM (100 mL), was added dropwise chlorotriisopropylsilane (6.36 g, 33 mmol) at rt. The reaction mixture was stirred for lh and then water was added. The organic layer was washed with brine dried over Na2504 and concentrated under vacuum. The residue was purified by column chromatography (silica gel, DCM) to afford tert-butyl (4-(2-((triisopropylsilyl)oxy)ethyl)phenyl)carbamate (11.7 g, 99%) as a white solid.

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-Boc-2-(4-Aminophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 24243-71-8, 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. 24243-71-8, name is Propane-1-sulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

To a 100-mL rm.md-hottom flask ‘.Vas added 2-[(1S,4S,5R)-5-[[5-cydopropyl-3-(2,6-dichorophenyl)-1 ,2-oxazol-4-yl]carbonyloxy ]-2-azahicyclol2.2.l]heptan-2-yl]-4-fluoro-l,3-benzothiazole-6-carboxylic acid I-1 (150 mg, 0.25 mmol, 1.0 equiv), dichloromethane (15mL), propane-1-sulfonamide (47 mg, 0.38 mmol, 1.5 equiv.), 4-dimethylaminopyridine (4715 mg, 0.38 mmoL 1.5 equiv), and EDC1 (73 mg, 0.38 mmol, 1.5 equiv) and the resultingmixture was stirred at room temperature for 16 h. 1 00 mL of brine was added and theaqueous mixture was extracted w·ith dichloromethane (l 00 mL x .5). The combined organicextracts ‘.vere dried over anhydrous sodium sulfate, filtered, and concentrated under reducedpressure. The residue was dissolved in 2 mL ofDMF and purified by Prep-HPLC using the20 follo·wing conditions: Column, XBridge C18 OBD Prep Column, 19 mm x 250 rnm; mobilephase, water (0 05% TFA) and ACN (68% to 84% over 8 min): Detector, UV 254 nm, toprovide 48.9 mg (28%) of(lS,4S,5R)-2-[4-fluoro-6-l(propane-l-sulfonyl)carbamoyl]-1,3-benzothiazol-2-y l]-2-azabicydo[2.2.1]heptan-5-y 5-cy dopropy l-3-(2,6-dichlorophenyl)-1 ,2-oxazole-4-carboxylate l-32 as a white solid. 1H NMR (300 MHz, CD30D) 8: 8.08 (d, J = 1.72.5 Hz, 1H), 7.70 — 7.49 (m, 4H), 5.00 (d, J ··· 6.6 Hz, lH), 4.41 (s, lH), 3.62—3.47 (m, 3H),3.23 (s, 1H), 3.00 (p, J 6.7 Hz, 1H), 2.60 (s, 1H), 2.25 (ddd, J 14. L 7.1, 2.5 Hz, lH),199- 1.78 (m, 2H), 1.71 (d, J = 10.6 Hz, HI), l.41- l.28 (m, 6H), 1.10 (t J = 7.5 Hz, 3H). MS (ES, m/z): [M+1l ” 693.25.

The chemical industry reduces the impact on the environment during synthesis Propane-1-sulfonamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics