Author: tianli

19982-07-1, 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. 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

Add 38.9g of Compound A to a 500ml three-necked flask,The reaction bottle was placed in an ice-water bath, then 21.4ml of nitric acid was added, and then 270.4ml of sulfuric acid was slowly added, and the addition was completed in about 40 minutes. After the addition, the temperature was slowly raised to room temperature and the reaction was completed for 4h. Post-treatment: Pour the reaction solution into 1L of ice water, stir the reaction thoroughly after quenching, add dichloromethane (200ml ¡Á 5) for extraction, wash with saturated sodium chloride solution 300ml, dry with anhydrous magnesium sulfate, filter, the filtrate is reduced at 45 Autoclaved,The residue was recrystallized from ethyl acetate / n-hexane (V / V = 100ml / 100ml) at 0 C.After filtration, the filter cake was dried under vacuum (-0.09MPa) at 40 C for 3h to obtain 14.5g of product compound D. Yield: 34.8% and GC purity: 99.1%.

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Reference:
Patent; Chongqing Zhien Pharmaceutical Co., Ltd.; Chongqing Liujiang Pharmaceutical Technology Co., Ltd.; Mu Xiang; Zhang Wei; Han Juan; Li Yufang; Deng Xianglin; Xiang Yong; (9 pag.)CN110938006; (2020); A;,
Amide – Wikipedia,
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16066-84-5, These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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.

tert-butyl [4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl]-methyl-carbamate Under an argon atmosphere 13 mg (0.96 mmol) tert-butyl methyl-carbamate, 11 mg (0.019 mmol) Xantphos, 8.8 mg (0.010 mmol) Pd2 dba3 and 47 mg (0.15 mmol) caesium carbonate were added to 50 mg (0.10 mmol) 1-[6′-chloro-4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 1.00 mL dioxane and the mixture was refluxed for 15 h with stirring. The reaction mixture was evaporated down i. vac. and the residue obtained was used in the next step without further purification. Yield: 59 mg (quantitative) Rt (HPLC): 1.70 min (method B)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16066-84-5.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

A mixture of 1-benzyl-piperazine (1.0 g, 5.67 mmol), 2-chloro-LambdaA-methylacetamide (671.2 mg, 6.24 mmol, 1.1 eq.), and potassium carbonate (941 mg, 6.81 mmol, 1.2 eq.) in anhydrous THF (23 mL) was stirred at 60 0C under N2 for 18 h. The mixture was cooled to rt and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC(Biotage.(R)., gradient elution 1:4:5 v/v MeOH:Acetone:DCM) to give 1.16 g (83percent) of the product as a white solid. 1H-NMR (300 MHz, DMSO-alphafe) .delta 7.62 to 7.56 (broad d, 1H),7.33 to 7.20 (m, 5H), 3.45 (s, 2H), 2.85 (s, 2H), 2.58 (d, 3H), 2.44 to 2.33 (broad s, 8H);ES-MS m/z 248.2 [M+H]+, RT (min) 0.33.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

61903-11-5, 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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below.

iii) 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]amide (1.5 g, 4.26 mmol) was dissolved in DMF (15 mL), and sodium iodide (0.64 g, 4.26 mmol) was added followed by N-acetylhomopiperazine (0.56 mL, 4.26 mmol) and diisopropylethylamine (0.74 mL, 4.26 mmol). The reaction was stirred under N2 at 50 C. for 18 hrs. Upon reaction completion (as monitored by LCMS), the solvent was removed at reduced pressure and the resulting oily residue was dissolved in DCM (20 mL), washed with sat. Na2CO3 (2¡Á20 mL) and sat. NaCl (2¡Á20 mL), and dried over Na2SO4. Upon solvent removal, 1.7 g of crude product as a thick oil were obtained. The product was purified by SiO2 chromatography (10 g cartridge-flash SI II from IST) employing DCM and DCM:MeOH 9:1 to yield 0.92 g of pure product and 0.52 g of less pure product. A second purification of the impure fractions using a 5 g SiO2 cartridge was performed using the same eluent. Overall, 1.09 g of 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide were obtained (2.64 mmol, 62% yield) as a thick light yellow oil. MS (ES+): 414.26 (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; SIENA BIOTECH S.P.A.; US2009/181953; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, This compound has unique chemical properties. The synthetic route is as follows., 2675-89-0

To a stirred suspension of N-(4-(3-(5-tert-butylisoxazol-3- yl)ureido)phenyl)-5-(pyrrolidin-3-yloxy)picolinamide hydrochloride (150 mg, 0.30 mmol) in CH3CN (3 mL) was added TEA (126 muEpsilon, 0.90 mmol), KI (10 mg,0.060mmol), and 2-chloro-N,N-dimethylacetamide (21 muEpsilon , 0.30 mmol). The resulting mixture was heated at 85 C for 1 h. LC-MS indicated that the reaction was complete. The reaction mixture was evaporated under reduced pressure and the residue was purified by reverse phase HPLC to give N-(4-(3-(5-tert-butylisoxazol-3- yl)ureido)phenyl)-5 -( 1 -(2-(dimethylamino)-2-oxoethyl)pyrrolidin-3 – yloxy)picolinamide (110 mg, 67%). LC-MS (ESI) m/z 550 (M + H)+.

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Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; WO2011/150198; (2011); A1;,
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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, A new synthetic method of this compound is introduced below., 239074-29-4

Step 2 Preparation of Ay-(3-chloro-4-fluorobenzyl)-6-(2-((frans-4-amiotanocvclohexyl)methyl)-2/-/-tetrazol- 5-yl)pyriotamiotadiotane-4-carboxamiotadelambda/-(4-Fluoro-3-chlorobenzyl)-6-(2H-tetrazol-5-yl)py?miotadiotane-4-carboxamiotade (0 71 g, 2 1 mmol) and commercially available tert-butyl frans-4-(hydroxymethyl)cyclohexylcarbamate (585 mg, 2 55 mmol) were taken up in tetrahydrofuran (20 mL) and treated with polymer supported triphenylphosphme (1 19 g, 2 55 mmol) After stirring for 30 mm at room temperature, di-tert-butyl azodicarboxylate (735 mg, 3 19 mmol) was added After 15 h at room temperature, the reaction was filtered to remove the resin The filtrate was concentrated to a crude oily residue The residue was purified via normal phase chromatography (silica, 0-75% ethyl acetate/heptane with a trace 1 % methanol ran through entire gradient) to afford the protected amine (1 08 g, 93%, 1 99 mmol) which was taken up in dichloromethane (5 mL) and treated with trifluoroacetic acid (2 0 mL, 15 mmol) After the reaction was stirred at ambient temperature for 3 h, the mixture was diluted with dichloromethane (5 mL) and neutralized with 2 5 N aqueous NaOH to achieve pH 7-8 The organic layer was separated, washed with water (3 mL), then dried over sodium sulfate, and concentrated to afford the title compound as an amber oil (0 87 g, 92%) LC/MS (5%-95% CH3CN/H2O, 6 mm) 2 24 mm, m/z 445 (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; PFIZER INC.; WO2009/16498; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1197-22-4, Adding some certain compound to certain chemical reactions, such as: 1197-22-4, name is N-Phenylmethanesulfonamide, 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 1197-22-4.

A solution of N-phenylmethanesulfonamide (0.800 g, 4.673 mmol), sodium hydride (60.00 %, 0.224 g, 5.607 mmol) and methyl 4-(bromomethyl)-3-fluorobenzoate (1.270 g, 5.140 mmol) in N,N-dimethylformide (10 mL) was stirred at the room temperature for 5 hr. Then, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The residue was chromatographed (5i02, 12 g cartridge; ethyl acetate / hexane = 0 % to 50 %) togive methyl 3-fluoro-4-((N-phenylmethylsulfonamido)methyl)benzoate as yellow solid(0.752 g, 47.7 %).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1197-22-4.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1,Some common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, molecular formula is C2H2F3NO, 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 stirred suspension of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfnyl)ethyl]-l-naphthalenecarboxamide (i.e. the title product of Step B) (180 mg), 2,2,2-trifiuoroacetamide (75 mg), MgO (53 mg), and Rh2(OAc)4 (4 mg) in dichloromethane (4 mL) was added PhI(OAc)2 (160 mg) at room temperature. The resulting mixture was stirred for 5 h at room temperature, then filtered through a short pad of Celite diatomaceous filter aid, and rinsed with ethyl acetate. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetate (3:7 to 1 :9) as eluent to afford the title compound, a compound of the present invention, as yellow oil (100 mg, 46% yield). 1H NMR (CDCl3) delta 8.80 (d, IH), 8.26 (d, IH), 7.42-7.65 (m, 7H), 6.99 (br t, IH), 4.24 (d, IH), 4.11 (m, 2H), 3.89 (d, IH), 3.82 (m, 2H), 3.48 (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 2,2,2-Trifluoroacetamide, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/154528; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of carboxylic acid (1.0 eq), amine (1.0-1.5 eq), N,N-diisopropylethylamine or triethylamine (1.5-3.0 eq) and a coupling agentsuch as HBTU (2-(1H-benzotriazol-i-yl)-i,i,3,3- tetramethyluronium hexafluorophosphate), HATU (1 -[Bis(dimethylamino)methylene]-i H-i 2,3-triazolo[4,5-b]pyridinium 3-oxidhexafluorophosphate) or HCTU (O-(i H-6-Chlorobenzotriazole-i -yl)1,1 ,3,3-tetramethyluronium hexafluorophosphate (1.0-1.5 eq) in anhydrous solvents such as DMF or DCM was stirred at room temperature for 1-72 h. The product was isolated and purified using one of the following methods: Step 4: Amide coupling of (S)-1 -[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-phenyl- butyryl]-pyrrolidine-2-carboxylic acid (280 mg, 0.72 mmol) with 1-(N-boc-aminomethyl)-4-(aminomethyl)benzene (170 mg, 0.72 mmol) was carried out following General Method I using HATU (330 mg, 0.86 mmol) and DIPEA (0.30 mL, 1 .7 mmol) in DCM (50 mL). Purification by column chromatography (biotage, 0-80% EtOAc/petrol) gave ((R)-1-{(S)-2-[4-(tert- butoxycarbonylamino-methyl)-benzylcarbamoyl]-pyrrolidine-1 -carbonyl}-3-phenyl-propyl)-methyl-carbamic acid tert-butyl ester (230 mg, 51%) as a colourless oil.AnalpH2_MeOH_4MIN: Rt: 3.51 mi mlz 609 [M+H]

The synthetic route of 108468-00-4 has been constantly updated, and we look forward to future research findings.

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

7341-96-0, These common heterocyclic compound, 7341-96-0, name is Propiolamide, 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.

Propiolamide (2.1 g, 31 mmol), 2,5-hexanedione (5.1 mL, 43 mmol) and para-toluenesulfonic acid monohydrate (300 mg, 1.6 mmol) were taken up in fluorobenzene (110 mL) and the reaction was heated at reflux under Dean-Stark conditions (24 h). The reaction mixture was cooled to room temperature and sodium carbonate (800 mg, 7.5 mmol) was added. The reaction mixture was stirred at room temperature (30 min) and the solids were removed by filtration. The solvent was removed and the residue was purified by column chromatography (5% ethyl acetate in hexanes). Following the elution of the title compound,the column was flushed (10% methanol in dichloromethane). The solvent was removed from the column residue and to this was added 2,5-hexanedione (3.6 mL, 31 mmol), para-toluenesulfonic acid monohydrate (300 mg, 1.6 mmol) and fluorobenzene (100 mL). The mixture was heated at reflux under Dean-Stark conditions (20 h). The reaction mixture was cooled to room temperature and sodium carbonate (800 mg, 7.5 mmol) was added. The mixture was stirred at room temperature (30 min) and the solids were removed by filtration. The solvent was removed and the residue was purified by column chromatography (5% ethyl acetate in hexanes). The two batches of the title compound were combined and further purified by column chromatography (5% ether in hexanes) to give the title compound (1.92 g, 42%) as a pale yellow solid. Rf: 0.59 (20% ether in hexanes); deltaH (300 MHz; CDCl3): 5.84 (2 H, s), 3.42 (1 H, s), 2.49 (6 H, s); deltaC (75 MHz; CDCl3): 151.1 (C), 131.5 (2C), 112.5 (2CH), 82.3 (CH), 78.0 (C), 16.5 (2Me); mp: 70-71 C (lit.[3] 68 C).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7341-96-0.

Reference:
Article; Law, Katherine R.; McErlean, Christopher S.P.; Tetrahedron Letters; vol. 57; 29; (2016); p. 3113 – 3116;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics