Amides-buliding-blocks

Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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. 3984-14-3

To a solution of 4-{[4-chloro-3-(trifluoromethyl)phenoxy]methyl}benzoic acid (Preparation 16, 237 mg, 0.72 mmol) in dichloromethane (8 ml_) was added EDCI (344 mg, 1 .79 mmol) followed by addition of N,N-dimethylsulfamide (222 mg, 1 .79Calculation isn’t correct mmol). The reaction was left to stir at room temperature for 3 hours. A solution of KHSO4 (10ml_) was added and the mixture separated using a phase separation cartridge. The organics were dried in vacuo to yield a white solid as the title compound (285 mg, 97%). 1 NMR (400 MHz, CDCI3): delta 2.95 (s, 6H), 5.10 (s, 2H), 7.00 (dd, 1 H), 7.23 (d, 1 H), 7.36 (d, 1 H), 7.49 (d, 2H), 7.89 (d, 2H). LCMS Rt = 1 .74 minutes MS m/z 406 [M35CI-H]”

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3984-14-3, its application will become more common.

Reference:
Patent; PFIZER LIMITED; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2013/88315; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, molecular formula is C4H8ClNO, 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. 2675-89-0.

Step 3: 2-[2-(3-Butoxyphenyl)-(tert-butoxycarbonyl)ethylamino]-N,N-dimethylacetamide To a suspension of NaH (60%, 2.0 g, 51 mmol) in dry DMF (125 ml) cooled at 0 C., a solution of 2-(3-butoxyphenyl)-(tert-butoxycarbonyl)ethylamine (7.5 g, 25.5 mmol) in dry DMF (125 ml) was added dropwise. After 1 h at room temperature, 2-chloro-N,N-dimethylacetamide (5.2 ml, 51 mmol) was added and the mixture was stirred for 16 h at room temperature. H2O (10 ml) was added and the solvent was evaporated under reduced pressure. The residue was dissolved in H2O (150 ml) and extracted with CH2Cl2 (2*150 ml). The collected organic phases were dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (petroleum ether/EtOAc 4:6) affording the title compound (7.2 g, 75%) as light yellow oil. 1H NMR (300 MHz, DMSO-d6): delta 7.1 (m, 1H), 6.79-6.71 (m, 3H), 3.97 (t, J=6.0 Hz, 2H), 3.96 (s, 2H), 3.40 (dd, J=8.7 Hz, J=7.2 Hz, 2H), 2.88 (s, 6H), 2.76 (dd, J=7.9 Hz, J=6.4 Hz, 2H), 1.76 (m, 2H), 1.46 (m, 2H), 1.37 (s, 9H), 0.95 (t, J=7.3 Hz, 3H). ESI+MS: calcd for C21H34N2O4: 378.52; found: 379.0 (MH+).

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

Reference:
Patent; NEWRON PHARMACEUTICALS S.P.A.; US2010/210631; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16066-84-5, 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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below.

[00724] Step E: To a stirred solution of (1S,2S,5R)-5-(6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2-phenoxycyclohexan-1-ol (78 mg, 0.18 mmol) and tert-butyl methylcarbamate (121 mg, 0.92 mmol) in 600 muL of dioxane was added Cs2CO3 (120 mg, 0.37 mmol) followed by 2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (34 mg, 0.074 mmol). The reaction mixture was sparged with argon for 5 minutes and then Pd2(dba)3 (34 mg, 0.037 mmol) was added and the vial was capped and heated to 100 C overnight. The reaction mixture was partitioned between dichloromethane (15 mL) and water (15 mL), extracted 3 x 15 mL with dichloromethane, dried over MgSO4, filtered and concentrated. The residue was purified over silica gel (0% to 75% ethyl acetate in hexanes) to afford tert-butyl (1-((1R,3S,4S)-3-hydroxy-4-phenoxycyclohexyl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(methyl)carbamate (30 mg, 31% yield).

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; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

550-89-0, 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. 550-89-0, name is Phenazine-1-carboxamide, A new synthetic method of this compound is introduced below.

Synthesis of the specific process: phenazine-1-carboxamide hydrolysis under acidic conditions to produce phenazine-1-carboxylic acid;Take 20mmol of phenazine-1-carboxylic acid (0.4577g) and 200ml of thionyl chloride was added to a 500ml round bottom flask, the installation of a reflux reaction device (using anhydrous calcium chloride drying tube), magnetic stirring, reflux reaction 6h, After cooling, the thionyl chloride was removed by rotary evaporation to obtain the intermediate phenazine-1-carbonyl chloride, which was used for the next reaction without purification;The obtained phenazine-1-carboxylic acid chloride was dissolved in 200ml of dry dichloromethane (DCM), added into a 500ml dry round bottom flask, protected by nitrogen, magnetically stirred, placed in an ice-water bath and cooled, and then 11.15 ml triethylamine (80 mmol, 4 equiv.) and2.367 g of 3-methoxy-1-propylamine(20mmol, 1equiv.) After the addition of ice water bath was removed at room temperature for 14h, intermittent sampling,The reaction was monitored by TLC. After DCM was removed by rotary evaporation, the reaction mixture was extracted three times and extracted with 450 ml of liquid (ethyl acetate and H 2 O in a volume ratio of 2: 1) each time. The combined organic phases were dried over anhydrous sodium sulfate for 12 h, filtered, EA washed the solid sodium sulfate, rotary steam, in order to transform the compoundProduct 15-1, 1.4883 g, 22.93% yield.

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; Hunan Agricultural University; Zhang Ya; Liao Xiaolan; Liu Shuangqing; Xiang Yaqin; (7 pag.)CN106922679; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1103234-56-5, Adding a certain compound to certain chemical reactions, such as: 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, 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 1103234-56-5.

EXAMPLE 4 Propane-1-sulfonic acid {3-[5-(4-chloro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide (1) A suspension of sulfonamide acid (9) (1.2 eq.) in CH2Cl2 was treated at room temperature with cat. amount of DMF (0.11 eq.). Within 30 min a solution of oxalylchloride (1.30 eq.) in CH2Cl2 was added and the reaction mixture was stirred for 2 h, whereby the corresponding acid chloride was formed. A suspension of aluminium chloride (AlCl3, 4 eq.) in CH2Cl2 was treated at 0 C. with a solution of Cl-phenyl azaindole (8) in CH2Cl2. To the reaction mixture was subsequently added at room temperature the freshly prepared (above described) acid chloride. Stirring at room temperature for 3 h, aqueous work-up and crystallization from THF/heptane provided the title compound (1) as off-white powder in 85% yield. MS (Turbo Spry): 509 (48%), 507 (M+NH4+, 100%), 492 (40%), 490 (M+H+, 84%).

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, 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Brumsted, Corey James; Moorlag, Hendrik; Radinov, Roumen Nikolaev; Ren, Yi; Waldmeier, Pius; US2012/22258; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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 1; [0289 ] In this Example, the modafinil intermediate compound benzhydrylthioacetamide was oxidized to produce modafinil according to the processes described herein using various ratios of alcohol to organic acid and various reaction mixture temperatures.[0290] First, benzhydrylthioacetamide (10 g; MW = 257.35; 1.0 eq.), methanol, and acetic acid were charged to a 250 ml_ flask. Hydrogen peroxide (4.3 ml 1.05 eq.) was then charged to the resulting mixture over the course of about 5 minutes. The reaction was allowed to proceed for about 24 hours, with samples periodically taken for HLPC analysis. Several different trials using particular ratios of methanol and acetic acid at particular temperatures were performed. Results are illustrated in Tables 1-7, below.Table 1 : 20 ml_ methanol/20 mL acetic acid; 400CTable 2: 30 mL metha?ol/10 mL acetic acid; 400CTable 3: 35 mL methanol/5 mL acetic acid; 400C Table 4: 39 mL methanol/1 mL acetic acid; 400C [0291] As illustrated in Tables 1-7 above, the processes of the present invention are effective in producing modafinil at high yield and with relatively low sulfone impurity content. Specifically, as illustrated in Table 2, a reaction mixture comprising 30 mL of methanol and 10 mL acetic acid (i.e., methanol and acetic acid are present in the reaction mixture at a ratio of about 3:1 ) with the oxidation reaction proceeding at 400C is particularly effective, producing modafinil at about 96% yield with a sulfone impurity content of about 0.22%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; MALLINCKRODT INC.; WO2007/70238; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, 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. 57561-39-4 name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, 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.

To a solution of tert-butyl (2-hydroxyethyl)(methyl)carbamate (1.0 g, 5.71 mmol) and triethylamine (1.15 g, 11.41 mmol) in dichloromethane (20 mL) was added dropwise methanesulfonyl chloride (975.86 mg, 8.56 mmol). The mixture was stirred at 0 C. for 1 hour. The resulting solution was washed with water and the organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum to afford 2-[tert-butoxycarbonyl(methyl)amino]ethyl methanesulfonate (1.29 g, 5.08 mmol) as a colorless oil. LCMS (ESI) [M+H]+=254

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-hydroxyethyl)(methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

915087-25-1, The chemical industry reduces the impact on the environment during synthesis 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

Compound I (100 g, 0.594 mol) is suspended in 300 mL of dioxane. TEA (250 mL, 3.59 mol) is added by pouring in a thin stream. The system is placed under nitrogen, and heated to 60C. A solution of intermediate II (160 g, 0.90 mol) in 150 mL of dioxane is prepared separately. The solution of compound II is added to the suspension in the reactor and left to react for about 20 hours. The mixture is cooled to l5C and filtered through a Biichner funnel, washing the cake twice with 100 mL of dioxane each time. The resulting product is suspended in 1200 mL of water, 1M HC1 is added until a pH < 3 is reached, and the resulting suspension is then filtered through a Buchner funnel, washing the cake twice with 200 mL of water each time. The crystal thus isolated is dried under vacuum at the temperature of 60C, providing intermediate III in a 76% yield (120 g, 45.1 mmol) and 99.6% HPLC purity. NMR (300MHz, CDCh) d 15.3 (m, 4H), 2.58 (t, br, 2H), 2.73 (s, 3H), 6.00 (m, 1 H), 6.22 (s, 1 H), 7.17 (s, 1H), 7.46 (s, 1H), 7.65 (d, 1H), 12.63 (m, 1H). The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life. Reference:
Patent; OLON S.P.A.; GRANDE, Valentina; FERRETTI, Gabriele; NOVO, Barbara; (0 pag.)WO2019/229625; (2019); 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 121492-06-6 as follows. 121492-06-6

DMF (20 ml), QHL 014 (4.42 g, 9.2 mmol), N-BOC-N-methyl ethylenediamine (2.00 g, 12.5 mmol), HATU (4.20 g, 11 mmol) was added in a 50 ml single-necked flask. After stirring for 5 minutes, DIPEA (5 ml, 27.6 mmol) was added dropwise. Stir at room temperature until QHL014 is completely reacted. DMF was evaporated under reduced pressure, and the crude product was dissolved in ethyl acetate and washed with water. The organic phase was dried and purified by silica gel column chromatography (dichloromethane: methanol = 50:1 to 20:1) to obtain light yellow solid QHL 015 (4.81 g, yield 80%).

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yafei Shanghai Biolog Medicine Science & Technology Co., Ltd.; LIU, Yuan; LIU, Cheng; WANG, Haiyang; (43 pag.)EP3572420; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, 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. 402-46-0, name is 4-Fluorobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

INTERMEDIATE 12; This shows the preparation of 4-(4-chlorophenoxy)benzenesulfonamide.To a solution of 4-chlorophenol (128 mg) and 4-fluorobenzenesulfonamide (175 mg) in NMP (1 mL) was added caesium carbonate (326 mg) and the mixture was heated in a CEM Discover microwave at 130 C for 10 minutes. The reaction mixture was allowed to cool , and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over sodium sulfate. The filtrate was concentrated in vacuo, and the resulting brown oil was dissolved in diethyl ether and flashed through a short plug of silica. Concentration in vacuo gave an oil that was subjected to column chromatography, eluting with 30% ethyl acetate in iso-hexane to give the title compound 4-(4- chlorophenoxy)benzenesulfonamide (100 mg) as a waxy solid.1H NMR (300 MHz, DMSO) delta 7.92 – 7.82 (m, 4H), 7.52 (dd, 2H), 7.47 – 7.40 (m, 2H), 7.34 (br s, 2H).

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

Reference:
Patent; ASTRAZENECA AB; WO2006/75955; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics