Category: amides-buliding-blocks

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)+.

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:
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

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. 3144-09-0, name is Methylsulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3144-09-0

Reference Example 42 To a mixture of methane sulfonamide (1.96 g), triethylamine (3.2 mL), 4-(dimethylamino)pyridine (252 mg), and dichloromethane (30 mL) was added a mixture of di-tert-butyl dicarbonate (5.17 g) and dichloromethane (40 mL) at room temperature for 30 minutes. The mixture was concentrated after stirring for 2 hours, and the residue was distributed with ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl methylsulfonyl carbamate (2.44 g). 1H-NMR (300 MHz, CDCl3) delta: 1.52 (9H, s), 3.28 (3H, s).

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1553074; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, A common compound: 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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.

EXAMPLE 3;Preparation of Tamsulosin HydrochlorideTamsulosin Hydrochloride is also prepared according to this example by first repeating the initial reaction, cooling, and filtering steps of Example 2 to produce the filtrate at 0 C.Instead of using ammonia, the filtrate is then alkalinized with DIEA until a pH of 8.5 is obtained, and the desired product is extracted with 2 x 50 mL of AcOEt. The combined organic layers are then extracted twice with 50 mL of water at pH 6 (adjusted with HCl). The EPO aqueous phases are combined and the pH is again adjusted to 8.5 with DDEA, and the product is then extracted with 2 x 25 mL of AcOEt.The combined organic phases obtained from the extractions are dried over Na2SO4 and the solvent is evaporated to obtain 3.28 g of crude tamsulosin. The content of byproduct as determined by HPLC method 1 was 0.261% (area percentage).The residue is dissolved in ethanol (32 mL) and 1.65 mL (7.76 mmol) of ethanol HCl 4.7 N are charged. Then, the mixture is cooled down to 0 C and the solid is collected by filtration, washed with ethanol and dried in vacuum at 60 C until constant weight to yield 2.17 g (4.87 mmols, 26% molar yield) of tamsulosin hydrochloride. By subsequent analysis, the content of by-product (formula (VE)) by HPLC method 1 at this stage is 0.08 area %.The tamsulosin hydrochloride thus obtained is further purified by repeating twice the following procedure: treating with 29 mL of ethanol at 78 C, stirring for 30 minutes, cooling to 0 C, filtering, washing with ethanol and then drying at 60 C in vacuum until constant weight. After drying, 1.98 g of tamsulosin hydrochloride are obtained (4.45 mmols, 91% partial molar yield). (Assay: 100.21%; IR: matches the standard; melting point: 227.4-229.3 C; chemical purity: 99.31 area % by HPLC method 1; XRD (20), see Figure 1; content of byproduct (formula (VII)) by HPLC method 1 : 0.02 area %)

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, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICHEM, S.A.; WO2007/4077; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

109903-35-7, Adding a certain compound to certain chemical reactions, such as: 109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, 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 109903-35-7.

To the [NITRO-LH-INDAZOLE-3-CARBOXYLIC] acid (1 equiv. ) of Example 63A in DMF (0.3 M) was added EDC (1.2 equiv. ), HOBT (1.2 equiv. ), NMM (1.2 equiv. ) and then 4- [METHYLSULPHAMOYLMETHYL-PHENYLAMINE] (1.3 equiv. ) at room temperature. The reaction was heated to [70 C] for 2 hours and then stirred at room temperature for 48 hours. Water was added to the reaction mixture and the precipitated product was filtered. The solid was washed with water, then a small volume [OF MEOH,] and then dried in a vacuum oven to leave a yellow solid.

According to the analysis of related databases, 109903-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2004/14864; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics