Category: amides-buliding-blocks

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

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

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

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

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

360-64-5, 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. 360-64-5, name is 2-(Trifluoromethyl)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[Step 2] Ethyl 5-({[2-(Trifluoromethyl)phenyl]carbonyl}amino)-2,3-dihydro-1-benzofuran-7-carboxylate 1,4-dioxane (20 ml) was added to ethyl 5-bromo-2,3-dihydro-1-benzofuran-7-carboxylate (600 mg), 2-(trifluoromethyl)benzamide (501 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (96 mg), cesium carbonate (1.01g) and 140 tris(dibenzylideneacetone)dipalladium (114 mg). After degassing, the mixture was stirred at 100C under argon atmosphere for 24 hours. The reaction mixture was filtered off on celite, the solvent was removed under reduced pressure. The resultant residue was purified on silica gel column chromatography to obtain the titled compound (220 mg) as slightly yellow powder.

The synthetic route of 360-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 62009-47-6, name is 2-Aminomalonamide, 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 62009-47-6. 62009-47-6

Diethylaminomalonate Aminomalondiamide 2-Carbamido-3-hydroxypynazine To an aqueous solution of diethylaminomalonate (hydrochloride form) was added sodium hydrogenocarbonate (pH> 7). After extraction, the organic phase was evaporated under reduced pressure and treated with an ammoniacal solution of methanol at 80C overnight to give aminomalondiamide quantitatively. This compound was used for next step without purification and dissolved in water. To that solution was added glyoxal sodium bisulfite hemihydrate, this reaction mixture was stirred at 90C for 3h, and then made basic with 58% NH4OH. Then, 30% H2O2 was added dropwise with rapid stirring to the cold solution (0C) [J. Med. Chem. 1983, 26, 283-86, J. Heterocyclic Chem. 1979, 16, 193]. The reaction mixture was allowed to warm at room temperature and the desired 2-hydroxy-3- carboxamidopyrazine precipitated. The solid was collected (63% yield) and part of it recrystallized.

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 2-Aminomalonamide.

Reference:
Patent; IDENIX (CAYMAN) LIMITED; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2007/144686; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 863127-76-8, name is (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide, 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. 863127-76-8

Example 2[0157] To a mixture of compound 1 (5.30 g, 22.11 mmol) in 1,4-dioxane (100 mL) and water (70 mL) was added NBS (4.40 g, 24.72 mmol) at -10 to 0 C. The slurry was warmed and stirred at 20-22 C for 3 h. Thiourea (1.85 g, 26.16 mmol) was added and the mixture heated to 100 C. After 2 h, the resulting solution was cooled to 20-22 C and cone, ammonium hydroxide (6 mL) was added drop wise. The resulting slurry was concentrated under vacuum to about half volume and cooled to 0-5 C. The solid was collected by vacuum filtration, washed with cold water, and dried to give 5.4 g (90% yield) of compound 2 as deep-yellow solids. 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 7.09-7.29 (m, 2H, J=7.5), 7.29-7.43 (d, IH, J=7.5), 7.61 (s, 2H), 7.85 (s, IH), 9.63 (s, IH); ESI-MS: calcd for (C?HioClN3OS) 267, found 268 MH+).

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 863127-76-8.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; KORONIAK, Lukasz; DESAI, Neil; WO2010/144338; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

19982-07-1, Adding some certain compound to certain chemical reactions, such as: 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, 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 19982-07-1.

l-Acetamido-3,5-dimethyl adamantane (40.0 g) was added to reaction vessel followed by addition of sodium hydroxide (57.80 g) and DEG (200 mL) at 25-300C. The reaction mixture was stirred and then heated at 155-1700C and heating was maintained for 10 Hrs. The reaction mixture was cooled to 80-850C and water (1600 mL) was added within 1 Hr. Reaction mixture was stirred for 30 minutes and toluene (500 mL) was added to the reaction mixture and further stirred for 1 Hr. After stirring the layers were settled for 30 minutes and then separated out. The organic (Toluene) layer was kept and to the aqueous layer, toluene (300 mL) was added and stirred for 1 Hr and after stirring layers were settled and separated out. Total toluene layers were collected and water (500 mL) was added to it and stirred for 1 Hr at 25-300C. After stirring the layers were settled for 30 minutes and then separated out. Organic (toluene) layer was dried over anhydrous sodium sulfate and wash the bed with toluene (50 mL)and then toluene was distilled under reduced pressure below 600C to afford the title compound Memantine Base.; Example 3 (b): Preparation of Memantine Base (One pot synthesis) l~Bromo-3,5-dimethyl adamantane (60.0 g) was added to reaction vessel followed addition of acetamide (87.42 g) the reaction mixture was stirred and heated at 130-1400C for 3 to 5 Hrs. The reaction mixture was cooled up to 80- 850C and then toluene (300 mL) was added to reaction mixture and stirred for 1 Hr. The reaction mixture was treated with water (600 mL) and stirred for lhr. The reaction mixture was filtered and washed with toluene. The organic layer was separated and toluene was distilled out at temperature range 105-130C.Cool to 105-1150C and the reaction mass was again treated with DEG(270 mL) at 105-1150C maintaing 105-1150C for 2 hrs. Again distill out toluene at 130-140C.Cool at 105-1150C and add sodium hydroxide (78 g) was added at 105-1150C. The reaction mixture was stirred and then heated at 155-1700C and heating was maintained for 10 Hrs. The reaction mixture was cooled to 80-850C and water (200 mL) was added within 1 Hr. Reaction mixture was stirred for 30 minutes and toluene (400 mL) was added to the reaction mixture and further stirred for 1 Hr. After stirring the layers were settled for 30 minutes and then separated out. The organic (Toluene) layer was kept and to the aqueous layer, toluene (50 mL) was added and stirred for 1 Hr and after stirring layers were settled and separated out. Total toluene layers were collected and water (500 ml) was added to it and stirred for 1 Hr at 25-300C. After stirring the layers were settled for 30 minutes and then separated out to afford the title compound Memantine Base.

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 19982-07-1.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2008/62472; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, I believe this compound will play a more active role in future production and life. 112101-81-2

10 g of (-)- (R)-5- (2- (2- (2-ethoxyphenoxy) ethylamino)-1-propyl)-2-methoxybenzene sulphonamide hydrochloride (TH) from Example 2 is recrystallised from mixtures of methanol and ethanol. Analysis : Methanol HPLC-composition Quantity of Yield HPLC-composition to ethanol of the starting raw solvent of the product* ratio material* used 100 : 0 TH 86. 1 % 120 mi 7. 77 g TH 95. 84 % impurity (2) 1. 53 % (77. 7 %) impurity (2) 0. 09 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 1. 79 % impurity (4) 0. 24 % impurity (5) 0. 98 % impurity (5) 0. 05 % impurity (6) 6. 17 % impurity (6) 3. 73 % 90 : 10 TH 86. 1 % 75 g TH 95. 5% impurity (2) 1. 53 % (77, 5%) impurity (2) 0. 12 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 1. 79 % impurity (4) 0. 31 % impurity (5) 0. 98 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 3. 94 % 70 : 30 TH 86. 1 % 210 ml 7, 78g TH 95. 9 % impurity (2) 1. 53 % (77. 8 %) impurity (2) 0. 12 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 0. impurity 0. 31 % impurity (5) 1. 79 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 3. 49 % 50 : 50 TH 86. 1 % 340 ml 7. 41 g TH 99. 27% impurity (2) 1. 53 % (74. 1 %) impurity (2) 0. 15 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 0. 98 % impurity (4) 0. 32 % impurity 1. 79 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 0. 0 % 30 : 70 TH 86. 1 % 500 ml 7. 55 g TH 99. 28 % impurity (2) 1. 53 % (75. 5 %) impurity (2) 0. 17 % impurity (3) 1. 79 % impurity (3) 0. 0 % impurity (4) 0. 98 % impurity (4) 0. 32 % impurity (5) 1. 79 % impurity (5) 0. 10 % impurity (6) 6. 17 % impurity (6) 0. 0 % * impurity (2) = 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide impurity (3) = 2-(2-ethoxyphenoxy) ethylbromide impurity (4) = N-(2-(2-ethoxyphenoxy) ethyl)-5-(2-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (5) = 5-(2-(bis-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (6) = 1,2-bis (2-ethoxyphenoxy) ethane (6)

The chemical industry reduces the impact on the environment during synthesis 112101-81-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2005/63702; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics