Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, 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 18469-37-9, SDS of cas: 18469-37-9

N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0243) To a solution of 4-bromo-N,N-dimethylbenzamide (11.0 g, 48.23 mmol) in dioxane (300 mL) were added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.7 g, 57.89 mmol), Pd(dppf)Cl2 (3.5 g, 4.78 mmol) and potassium acetate (14.2 g, 144.69 mmol) at room temperature. The resulting mixture was stirred for 16 h at 100 C. The reaction mixture was cooled to room temperature and the resulting solid was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 40% gradient) to yield N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as orange solid (10.0 g, 70%). MS: m/z=276.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N,N-dimethylbenzamide, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6312-87-4, These common heterocyclic compound, 6312-87-4, name is N-(4-Phenoxyphenyl)acetamide, 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.

General procedure: Dimethylformamide (3 mmol) was added to N-phenylacetamides(2a-2g, 1 mmol) in an ice bath, then phosphoryl chloride(15 mmol) was added dropwise to the mixture and was stirredat ice bath for 20 min, then the reaction proceeded at temperature80e90 C for 7e10 h. After completion of the reaction, ice is addedto the mixture and was stirred, then the formed precipitate wasfiltrated and recrystallized in ethanol [31]. Compounds 3a, 3c, 3d, 3f and 6a were reported in the literatures[32e35].2.3.1. 2-Chloro-6-phenoxyquinoline-3-carbaldehyde (3b)Yellow solid; yield: 61%; mp: 110e113 C; 1H NMR (300 MHz-CDCl3) d 7.18e7.20 (d, 2H, J 6 Hz, AreH), 7.26e7.30 (t, 1H, J 6 Hz,AreH), 7.47e7.53 (m, 2H, AreH), 7.75e7.79 (m, 2H, AreH),8.08e8.11 (d, 1H, J 9 Hz, AreH), 8.92 (s, 1H, AreH), 10.37 (s, 1H,CHO).

The synthetic route of 6312-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirzaei, Salimeh; Hadizadeh, Farzin; Eisvand, Farhad; Mosaffa, Fatemeh; Ghodsi, Razieh; Journal of Molecular Structure; vol. 1202; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000698-88-3, name is tert-Butyl (2-amino-4,5-difluorophenyl)carbamate, 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 1000698-88-3, Quality Control of tert-Butyl (2-amino-4,5-difluorophenyl)carbamate

e) N-Benzyl-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-l-yll-2-cyclopentyl- acetamide; To a solution of 5.0 g (20.47 mmol) (2-amino-4,5-difluoro-phenyl)-carbamic acid tert- butyl ester (Example 73, intermediate g) in 50 ml methanol, 2.21 g (22.57 mmol) cyclopentanecarbaldehyde (commercially available) were added. After stirring for 5 min. at room temperature, 3.2 g (20.5 mmol) p-chlorobenzoic acid and 2.5 ml (20.47 mmol) benzyl isocyanide (commercially available) were added. After stirring for 19 h, 38.38 ml (153.52 mmol) 4 M hydrochloric acid in dioxane were added dropwise over 5 min. After 5 h the solution was poured on 500 ml saturated aqueous sodium bicarbonate solution and the phases were separated. The organic layer was extracted three times with ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n- heptane : ethyl acetate (100 : 0 to 50 : 50). Light yellow foam (97%). MS (Turbo Spray): m/z = 480.1 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-amino-4,5-difluorophenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BENSON, Gregory Martin; BLEICHER, Konrad; FENG, Song; GRETHER, Uwe; KUHN, Bernd; MARTIN, Rainer E.; PLANCHER, Jean-Marc; RICHTER, Hans; TAYLOR, Sven; WO2010/28981; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, 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 177906-48-8, name: trans-N-Boc-1,4-cyclohexanediamine

To a solution of 21.43g (0.1mol) of tert-butyl N-(trans-4-aminocyclohexyl) carbamate in 250mL of N,N-dimethylformamide were added 16.76mL (0.12mol) of bis (2-bromoethyl) ether and 34.85mL (0.25mol) of triethylamine, and the mixture was stirred for 6 hours at 70C. Then solvent was removed under reduced pressure and the residue was treated with ethyl acetate. The organic layer was washed with sodium carbonate aqueous solution and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform alone to chloroform/methanol = 30/1) to give 19.92g (70%) of the title compound.

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, trans-N-Boc-1,4-cyclohexanediamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 22958-64-1, 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. 22958-64-1 name is 2-(4-Sulfamoylphenyl)acetic acid, 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.

[00361] To a solution of 2-amino-6-(2,2,2-trifluoro-1 -phenylethyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridine-3-carbonitrile (Intermediate Core-2a_D) (60 mg, 0.178 mmol), 2- (4-sulfamoylphenyl)acetic acid Core-2a_6d (60 mg, 0.267 mmol), DIPEA (46 mg, 0.356 mmol) in DMF (10 ml.) was added aq. T3P (50% in EtOAc) (170 mg, 0.267 mmol) at 20 C. The mixture was stirred at 20 C for 1 h. The reaction was concentrated to oil and diluted with EtOAc (10 ml_), washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated to a yellow oil, which was purified by prep-HPLC (base) to get A/-(3-cyano-6-(2,2,2-trifluoro-1 – phenylethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-(4-sulfamoylphenyl)acetamide (18 mg, yield: 18%) as a yellow solid; 1H NMR (400 MHz, CD3OD) d 7.88 (d, =8.41Hz, 2H), 7.37- 7.59 (m, 7H), 4.51 -4.58 (m, 1H), 3.94 (s, 2H), 3.66-3.84 (m, 2H), 3.06-3.19 (m, 1H), 2.78-2.92 (m, 1H), 2.56-2.72 (m, 2H); LC-MS Rt 0.945 min, MS m/z [M+H]+ 535.1, Method 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Sulfamoylphenyl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 207405-60-5, These common heterocyclic compound, 207405-60-5, name is tert-Butyl 5-hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylate, 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.

Preparation of 2-Aza-2-(t-butoxycarbonyl)bicyclo[2.2.1]heptan-5-one STR36 Dimethylsulfoxide (85.9 mmol) was added to a solution of oxalyl chloride (39.5 mmol) in dichloromethane (100 mL) at -78– C. Stirred for 20 minutes whereupon [exo]2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-ol (35.7 mmol) in dichloromethane (50 mL). Stirred at -78– C. for 3 hours then triethylamine (179 mmol) was added to the reaction then warmed to room temperature for one hour. Brine was added then the reaction was extracted with dichloromethane (3*200 mL). The organic extracts were dried over magnesium sulfate then evaporated. The residue was purified by preparative HPLC over silica gel eluding with 10% to 75% ethyl acetate in hexanes to yield 2-aza-2-(t-butoxycarbonyl)-bicyclo[2.2.1]heptan-5-one (31.3 mmol).

The synthetic route of 207405-60-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6124312; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 85006-25-3, 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. 85006-25-3 name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, 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.

Preparation 2 [tert-Butoxycarbonyl-[(4-methoxyphenyl)methyl]amino] tert-butyl carbonate A 20 L reactor, under nitrogen is charged with (tert-butoxycarbonylamino) tert- butyl carbonate (812.9 g, 3.48 mol), dimethylformamide (4.4 L), potassium carbonate (626.5 g, 4.52 mol) and l -(chloromethyl)-4-methoxy -benzene (462 mL, 2.56 mol). The mixture is stirred at 40 C overnight. lH NMR analysis shows incomplete reaction. Additional potassium carbonate (626.5 g, 4.52 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after 48 hours shows the reaction is still incomplete. Additional potassium carbonate (482 g, 3.49 mol) is added and the mixture is stirred at 40 C. lH NMR analysis after overnight reaction shows complete reaction with no starting materials remaining. Water (5 L) and MTBE (5 L) are added and the layers are separated. The organic layer is washed with water (3×3 L), dried over sodium sulphate, and concentrated to give the title compound (1.21 Kg, 98%). 1H NMR (d6-DMSO) delta 7.20 (d, J= 8.3 Hz, 2H), 6.91 (d, J= 8.3 Hz, 2H), 3.73 (s, 2H), 3.35 (s, 3H), 1.41 (s, 18H).

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

Reference:
Patent; ELI LILLY AND COMPANY; MARTIN, Fionna Mitchell; WO2015/138208; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 7160-22-7, These common heterocyclic compound, 7160-22-7, name is N-(3,4-Dichlorophenyl)pivalamide, 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.

2b) Preparation of Compound 2; A solution of Compound 1 (50 g) in tetrahydrofuran (300 mL) was cooled to-50 – -4O0C under an inert atmosphere of nitrogen. N-Butyl lithium (2.5M in hexanes, 179 mL) was added at such a rate as to keep the solution’s internal temperature between -45 – -30 0C (ca. 15 – 30 min addition). The solution was held at ca. -35 – -25 0C until HPLC indicated that the initial reaction was complete. The solution was then recooled to – 45 – 4O0C, and sulfur dioxide (-16.9 g) was bubbled through the solution, keeping the internal temperature below approximately -14 0C, until the solution was acidic. When the reaction was complete, the mixture was warmed to -10 – 0 0C. Starting at -2 – 3 0C, sulfuryl chloride (25.2 mL) was then added dropwise to the tetrahydrofuran solution over 5 – 15 min, keeping the temperature below approximately 22 0C. After 5 min, HPLC confirmed reaction completion, while the solution was kept around 10 – 15 0C. The mixture was solvent-exchanged into alpha,alpha,alpha-trifluorotoluene under reduced pressure, filtered, partially concentrated under vacuum (to -100 mL), followed by addition of dichloromethane (350 mL). To this mixture was added a solution of piperazine (61.2 g) in dichloromethane (625 mL) at ambient temperature dropwise, keeping the solution’s internal temperature at 15 – 27 0C (2h addition). The reaction was held at 20 – 24 0C until complete. The mixture was washed with deionized water (200 mL), the organic layer concentrated, followed by addition of heptane (450 mL). The product (70.5 g) was isolated by filtration, washed with heptane (50-100 mL), and dried under vacuum at 50-55 0C.

The synthetic route of 7160-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39091; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 337463-88-4, 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 337463-88-4 as follows.

The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with water and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHC13) to afford a solid (2. 5g, 38%). MS (+ve ion electrospray) m/z 253 (MH+).

According to the analysis of related databases, 337463-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/2490; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1386861-46-6, name is 2-Chloro-6-methyl-N-phenylbenzamide, molecular formula is C14H12ClNO, 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. COA of Formula: C14H12ClNO

General procedure: 00685] To a stirred mixture of amide (E-2) (173 mmol, 1 eq) in anhydrous THF (250 mL) at -30 C under an argon atmosphere, a solution of n-butyllithium in hexanes (432 mol, 2.5 eq) is added dropwise over 30 min while keeping inner temperature between -30 C and -10 C. The resulting mixture is then stirred at -30 C for 30 min.[00686] To a stirred mixture of (S)-tert-butyl l-(methoxy(methyl)amino)-l-oxopropan-2- ylcarbamate (260 mmol, 1.5 eq) in anhydrous THF (250 mL) at -30 C under an argon atmosphere, a solution of isopropylmagnesium chloride in THF (286 mmol, 1.65 eq) is added dropwise over 30 min while keeping inner temperature between -30 C and -10 C. The resulting mixture is stirred at -30 C for 30 min. This solution is then slowly added to above reaction mixture while keeping the inner temperature between -30 C and -10 C. The resulting mixture is stirred at – 15 C for 1 h. The reaction mixture is quenched with water (50 mL) and then acidified with cone. HC1 at -10 C – 0 C to adjust the pH to 1-3. The mixture is allowed to warm to RT and concentrated in vacuo. The residue is dissolved in MeOH (480 mL), and then cone. HC1 (240 mL) is added quickly at RT. The resulting mixture is stirred at reflux for 1 h. The reaction mixture is concentrated in vacuo to reduce the volume to about 450 mL. The residue is extracted with a 2: 1 mixture of heptane and ethyl acetate (2 x 500 mL). The aqueous layer is basified with concentrated ammonium hydroxide to adjust the pH to 9-10 while keeping the inner temperature between -10 C and 0 C. The mixture is then extracted with DCM (3 x 300 mL), washed with brine, dried over MgSC>4 and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in MeOH (1200 mL) at RT. To this solution, D- (-) – tartaric acid (21g, 140 mmol, 0.8 eq) is added in one portion at RT. After stirring at RT for 30 min, white solid precipitates out and the mixture is slurried at RT for 10 h. The solid is collected by filtration and rinsed with MeOH (3 x 50 mL). The collected solid is suspended in water (500 mL) and then neutralized with concentrated ammonium hydroxide solution at RT to adjust the pH to 9-10. The mixture is extracted with DCM (3 x 200 mL). The combined organic layers are washed with brine, dried over MgS04 and filtered. The filtrate is concentrated in vacuo to afford (S)-3-(l -aminoethyl)-isoquinolin- 1 (2H)-ones (E-3).Amine 1-1 was prepared according to Method E and then coupled to (A-3) using Method I to provide compound 1-2. ESI-MS m/z: 428.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1386861-46-6, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics