Amides-buliding-blocks

Synthetic Route of 26638-53-9, A common heterocyclic compound, 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, molecular formula is C14H10ClNO3S, 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.

N-bromosuccinimide (187 mg, 1.05 mmol) was added portionwise to a solution of ketone 3f (308 mg, 1.0 mmol) and FeCla (324 mg, 2.0 mmol) in CH2CI2 (10 mL) and CH3CN (5 mL) , and the reaction mixture was stirred at room temperature for 3 h. Additional W-bromosuccinimide (187 mg, 1.05 mmol) was then added and the reaction mixture was stirred at room temperature for a further 14 h. The reaction mixture was washed with water and brine and dried over NaSCli. The crude product was purified by column chromatography ( CH2CI2 : hexane – 2:1) followed by crystallization from MeOH. The product 3k was obtained as a white solid (290 mg, 75 percent) . XH NMR (400 MHz, Acetone-dg) 3 8.31 (d, J = 2.5 Hz, 1H) , 8.00 – 7.96 (m, 1H) , 7.95 – 7.89 (m, 3H) , 7.58 (d, J = 8.7 Hz, 1H) , 3.44 (s, 3H) ; 13C NMR (101 MHz, Acetone-dg) delta 189.6, 142.0, 139.1, 139.0, 138.4, 135.3, 134.7, 134.3, 132.8, 127.9, 125.8, 119.4, 39.3; LR-MS calcci. for C ,HioBrClN03S [M+H]+ 387.92, found 388.63.

The synthetic route of 26638-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew C.; HENKE, Adam; GASSAWAY, Madalee M.; RIVERS, Marie-laure; JAVITCH, Jonathan A.; SAMES, Dalibor; WO2015/138791; (2015); A1;,
Amide – Wikipedia,
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Reference of 6873-44-5, The chemical industry reduces the impact on the environment during synthesis 6873-44-5, name is 4-Chloro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

General procedure: Methacryloyl chloride (2 equiv.) was added to a mixture of amide (1 equiv.), triethylamine (2 equiv.) and DMAP (0.1 equiv.) in dichloromethane (20 mL). The resulted mixture was stirred at 35 oC for 10-12 h. The reaction was quenched with saturated aqueous Na2CO3 (5 mL), and then the mixture was extracted with dichloromethane (3 x 5 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as the eluent) affording the corresponding N-alkyl-N-methacryloyl benzamides 1.

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, 4-Chloro-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Yu-Jue; He, Yan-Hong; Guan, Zhi; Tetrahedron; vol. 75; 22; (2019); p. 3053 – 3061;,
Amide – Wikipedia,
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Related Products of 22117-85-7, 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 22117-85-7 as follows.

EXAMPLE 9 Preparation of the compound of formula STR15 Benzyl-piperazine, PCl3 and 2-methoxy-5-sulphamoyl-benzoic acid were reacted in a reactor in accordance with the method described in Example 1. The product of formula STR16 was separated, and debenzylated by catalytic reduction with 5% Pd on C in ethyl alcohol. The 2-methoxy-5-sulphamoyl-benzoylpiperazine obtained in this manner was reacted with acetyl chloride in a molar ratio of 1:1, in benzene in the presence of pyridine, was filtered off, washed and crystallized from a mixture of methanol and ethyl acetate.

According to the analysis of related databases, 22117-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ravizza S.p.a.; US4940793; (1990); A;,
Amide – Wikipedia,
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Synthetic Route of 1015-89-0, A common heterocyclic compound, 1015-89-0, name is Phenanthridin-6(5H)-one, molecular formula is C13H9NO, 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.

EXAMPLE 28 STR46 To a mixture of phenanthridone 32 and PCl5 is added a molar excess of POCl3. The reaction is heated to reflux until chromatographic analysis indicates complete reaction, cooled and quenched by pouring onto ice. The aqueous layer is extracted with CHCl3. The organic layer is dried over MgSO4, filtered and evaporated to provide phenanthridine 33.

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; Merck & Co., Inc.; US5336674; (1994); A;,
Amide – Wikipedia,
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Synthetic Route of 618446-06-3, The chemical industry reduces the impact on the environment during synthesis 618446-06-3, name is 7-Amino-4,4-dimethyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one, I believe this compound will play a more active role in future production and life.

7-Fluoro-4,4-dimethyI-3,4-dihydro-lH-[l,8]naphthyridin-2-one; 7-Fluoro-4,4-dimethyl-3,4-dihydro-lH-[l,8]naphthyridin-2-one, was produced as follows: HF-pyridine (100 mL) was cooled to -42 0C in a 1000 mL HDPE bottle using an CH3CN dry ice bath. While stirring vigorously, 7-amino-4,4-dimethyl-3,4- dihydro-lH-[l,8]naphthyridin-2-one (24.6 g, 0.129 mol) was added portionwise to control the exotherm. After the addition, NaNO2 (8.9 g, 0.1291 mol) was added portionwise. Significant exotherms were observed for both additions. The reaction mixture was then allowed to warm to 0 0C and stir for 2 h. The reaction mixture was quenched into a 4 L high density polyethylene (HDPE) bottle full of ice. The aqueous slurry was then neutralized using 2 N KOH. The resulting aqueous solution was extracted 3 times with CH2Cl2. The organic layers were dried over Na2SO4, filtered and concentrated to dryness. Excess pyridine was azeotroped with heptane. The product was dried under vacuum (2 mm Hg) for 3 h. The resulting product, 7-fluoro-4,4- dimethyl-3,4-dihydro-lH-[l,8]naphthyridin-2-one, was in the form of a white powder (23.06 g, 0.119 mol, 92%). MS: APCI: M+l: 195.1 (Exact Mass: 194.09).

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, 7-Amino-4,4-dimethyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 39549-79-6, 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. 39549-79-6, name is 2-Amino-4-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 15 mL tube was added 2-aminobenzamide (1 mmol), benzyl amine (1.5 mmol), and a stir bar. Then H2O2 (30 wtpercent in H2O, 5 equiv.) was added by a syringe at room temperature under open air. The tube was closed and kept at 120¡ãC for 20 h. The conversion and yield were determined by GC and GC?MS using hexadecane (0.1 mmol) as the internal standard.

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, 2-Amino-4-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qi, Xin-Xin; Song, Zhen-Zhen; Gong, Jin-Long; Fang, Zheng-Yu; Wu, Xiao-Feng; Chinese Chemical Letters; vol. 27; 1; (2016); p. 21 – 24;,
Amide – Wikipedia,
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Application of 3984-14-3, A common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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.

Intermediate 3 1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3H) 1.59-2.04 (m, 7H) 2.74-2.82 (m, 1H) 2.88 (s, 6H) 7.57 (dd, J=8.42, 1.46 Hz, 1H) 7.74 (d, J=8.78 Hz, 1H) 7.91 (s, 1H) 11.71 (s, 1H) 12.08 (s, 1H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC for 2 h. After cooling to 30 oC, N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

The synthetic route of 3984-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/171015; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 solution of 2-amino-5-bromobenzamide (7.8 g, 0.036 mol), 4-methyl pentanoic acid (8.41 g, 0.O72mmol), and TBTU (17.46 g, 0.054 mol) in DMF (100 mL) was added DIPEA (25 mL, 0.154 mol) and the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was diluted with water (100 mL)and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with aq. sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, and the volatiles were evaporated to dryness. The residue was purified by silica gel column chromatography using a gradient of 40% ethyl acetate in hexanes and the required fractions were collectedand volatiles were evaporated to give 5-bromo-2-(4-methylpentanamido)benzamide (7.0 g, 0.022 mol, 55% yield) as a brown solid. LCMS (ESI) m/e 313.0 (bromo pattern) [(M+H), calcd for C13H18BrN2O2, 313.05]; LC/MS retention time (LC/MS Method = Column – YMC PACK TMS (3X5Omm), 3.0 rim; Mphase A: 2%MeCN98%H20 – 10mM NH4OAc; Mphase B : 98%ACN – 2%H20 -10 mM NH4OAC;Flow: 1.2 mL/min)): ti = 2.12 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromobenzamide, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); 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. 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 20348-09-8

EXAMPLE 1096-((l-(2-(3-Oxo-2H-pyrido[3,2-b][l,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-oneHydrochlorideStep 1tert-Butyl 1 -(2-(3-Oxo-2H-pyrido[3,2-b] [ 1 ,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylcarbamateTo a suspension of sodium hydride (38.0 mg, 55%) in N,N-dimethylacetamide (5 mL) was added 2H-pyrido[3,2-b][l,4]oxazin-3(4H)-one (151 mg) under cooling with ice, the mixture was stirred at room temperature for 30 minutes. The mixture was added AC (151 mg) under cooling with ice, the mixture was stirred at room temperature for 1.5 hours and further stirred at 60 C for 4 hours. The mixture was concentrated in vacuo. After dilution of the residue with ethyl acetate, the mixture was added saturated ammonium chloride solution under cooling with ice. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, chloroform : ethyl acetate = 2: 1) of the residue gave tert-butyl l-(2-(3-oxo-2H-pyrido[3,2-b][l,4]oxazin- 4(3H)-yl)ethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (84.0 mg).1H NMR (CDC13): delta 1.42 (s, 9H), 1.69-2.10 (m, 10H), 3.90 (s, 2H), 4.16-4.29 (m, 3H), 4.62 (d, J= 3.7 Hz, 2H), 6.90 (dd, J= 8.0, 4.9 Hz, 1H), 7.19 (dd, J= 7.3, 1.2 Hz, 1H), 8.01 (dd, J= 4.8, 1.2, Hz, 1H).MS (ESI+) m/z: 404 (MH+).HRMS (ESI+) for C2iH3oN305 (MH+): calcd, 404.21855; found, 404.21800.

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 20348-09-8.

Reference:
Patent; KYORIN PHARMACEUTICAL CO., LTD.; MERCK SHARP & DOHME CORP.; FUKUDA, Yasumichi; KAELIN, David E. Jr.; SINGH, Sheo B.; WO2013/3383; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 188345-71-3, name is 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, 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 188345-71-3, Safety of 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene

2.22 Preparation of Compound 4 A stream of O3 was bubbled through a solution of compound 3 (8.0 g, 41 mmol) in CH3CO2H (21 mL) and DCM (350 mL) at -50-60 C. until the solution turned blue. Excess O3 was removed with O2, and Me2S (7.7 mL) was added dropwise to the solution. The mixture was allowed to warm gradually to rt and stirred for 16 h under N2. The solution was concentrated and the residue was used for the next step directly.

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, 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartman, George D.; US2015/132258; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics