Tag: M.W=200-300

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

749927-69-3, A common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, molecular formula is C8H7BrFNO, 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.

Step 14-bromo-N-methyl-2- 14-(2,2,2-trifluoroethyl)piperazin-1-ylj benzamide4-Bromo-2-fluoro-N-methylbenzamide (1.17 g, 5.04 mmol) was dissolved in dimethyl sulfoxide (8 mL). 1-(2,2,2-Trifluoroethyl)piperazine (1.69 g, 10.05 mmol) and K2C03 (1.5511.22 mmol) were added, and the reaction mixture was heated to 120 C for 17 hours. The reaction mixture was partition between water (100 mL) and ethyl acetate (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over Mg504, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate, Rf=0.51) to give the titled compound (1.60 g, 83%). ?H NMR (300 MHz, DMSO-d6) 5 ppm2.75-2.80 (m, 7H), 2.92-2.95 (m, 4H), 3.24 (q. J=10.3 Hz, 2H), 7.25-7.28 (m, 2H), 7.48 (d, J=8.5 Hz, 1H), 8.58(q, J=4.4 Hz, 1H); MS(ESI+) m/z 380 & 382 (M+H).

The synthetic route of 749927-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; SCANIO, Marc; BUNNELLE, William; KOENIG, John Robert; DRIZIN, Irene; PLIUSHCHEV, Marina; COWART, Marlon; WO2015/112445; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

22227-26-5, 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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide, A new synthetic method of this compound is introduced below.

A, 1560 g of intermediate 2,6.24 L of ~ N ‘N-dimethylformamide was charged into a 50 L autoclave, and the reaction was cooled to 12 ¡ã C; B, adding sodium hydroxide in batches, And control the reaction system temperature does not exceed 15 ¡ã C, Add to continue stirring 20min; C, the reaction system is cooled to 10 ¡ã C, adding the magnesium chloride hexahydrate to the reaction system, the temperature of the reaction system is 10 ~ 15 D, the reaction system to room temperature, stirring 4h; E, with hydrochloric acid to adjust the reaction system pH to 2.2, and the body reaction system temperature below 20 ¡ã C; F was added to the reaction system by the addition of 5 L of methyl tert-butyl ether, and the layers were separated and then extracted with methyl tert-butyl ether (2.5 L X). The organic layers were combined and washed with saturated sodium chloride (2.5 LX 2); G, concentrated, the residue was added to petroleum ether beating and dried at room temperature to give 1931 g of intermediate 5;H, 1.9 kg of intermediate 5 and 8.9 kg of methanol were charged into a 50 L autoclave, and the reaction was cooled to 10 ¡ã C; I, dropping formylhydrazide into the reaction system; J, the reaction system to cool to 0 ¡ã C; K, 666 g of ethyl formate was added dropwise and the temperature was controlled at 0 to 5 ¡ã C; L, the reaction system temperature to 90 ~ 95 ¡ã C, and at this temperature for 6h; M, the reaction system to cool to 35 ~ 40 ¡ã C, and then to the reaction system by adding 28L of water; N, the addition of methyl tert-butyl ether 12L extraction, standing after the separation, the water phase and then 10L methyl tert-butyl ether extraction; combined organic layer, with saturated sodium chloride (6L X 2) O, the solvent was removed, the crude product was beaten with methylene chloride 3L at room temperature, filtered and dried to give 1.28 kg of intermediate 4 with a liquid phase purity of 98.6percent.

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; Guangzhou Wenhao Biological Technology Co., Ltd.; Chen Xinying; Xu Liang; Liu Wenzhong; (6 pag.)CN106831617; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, 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. 127828-22-2 name is tert-Butyl (2-(2-aminoethoxy)ethyl)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 chilled solution (-15 C) of 2 (1.41 g, 4.61 mmol) in THF (20 mL) was added N-methylmorpholine (NMM; 0.51 mL, 4.61 mmol) and subsequently isobutylchloroformate (IBCF; 0.61 mL, 4.61 mmol) under N2 atmosphere. After 5 min, a solution of 1 (0.857 g, 4.19 mmol) in THF (10 mL) was added dropwise at the same temperature, and the mixture was stirred for 30 min at the same temperature and then at room temperature for 1 h. After removing the solvent in vacuo, the residue was dissolved in ethyl acetate (50 mL). The organic phase was washed with 5% NaHCO3 (30 mL ¡Á 2), 5% citric acid (30 mL ¡Á 3), saturated NaCl solution (30 mL ¡Á 1), successively and dried over anhydrous MgSO4. After removal of the solvent in vacuo, the residue was subjected to flash chromatography on silica gel using a mixture of chloroform/methanol (100:1) as an eluent to provide 3 as a pale yellow solid (1.67 g, 80.6%) melting at 128-129 C. 1H NMR (CDCl3): delta 1.44 (9H, s, Boc), 3.17-3.51 (10H, overlapped, CH2), 4.76-4.78 (1H, dd, CH), 6.89 (1H, d, NH), 7.35-7.37 (2H, d, aromatic), 8.14-8.16 (2H, d, aromatic). ESI-MS (M+Na)+: m/z 515, found: 515. Anal. Calcd for C20H27N4O7F3: C, 48.78; H, 5.53; N, 11.38. Found: C, 48.46; H, 5.30; N, 11.21.

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

Reference:
Article; Suzuki, Hiroyuki; Kanai, Ayaka; Uehara, Tomoya; Guerra Gomez, Francisco L.; Hanaoka, Hirofumi; Arano, Yasushi; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 978 – 984;,
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

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

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