Author: tianli

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, 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 3984-14-3. 3984-14-3

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, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).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 C. for 2 h. After cooling to 30 C., 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 C. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 C. 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)+.

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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/227769; (2008); 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 2675-89-0 as follows. 2675-89-0

Prepared according to a procedure similar to that described for ethyldimethylphosphine borane I-23 starting from 2-chloro-N,N-dimethylacetamide (396 mg, 3.1 mmol) (except reaction performed at rt) to provide the title compound as a colourless oil (231 mg, 1.2 mmol, 84%).

According to the analysis of related databases, 2675-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AUSPHERIX LIMITED; KING, Nigel Paul; POWELL, Jonathan Raymond; NEGOITA-GIRAS, Gabriel; WATTS, Joseph Michael; ALVAREZ, Alicia Galvan; GUETZOYAN, Lucie Juliette; FREEM, Joshua Robert; CLARKE, Philip Graham; NAYLOR, Alan; (264 pag.)WO2018/220171; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1122-56-1, name is Cyclohexanecarboxamide, 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 1122-56-1. 1122-56-1

General procedure: The benzamide (0.2 mmol), NaH (3 equivalents) and dry THF(3 mL) were added to a two-neck flask in turn and stirred atroom temperature for 1 h. Then disulfide (1.5 equivalent) wasadded into the mixture and stirred for another 36 h at roomtemperature. During the whole reaction process, the systemwas kept turbid because of the difficult solubility of NaH inTHF. Then the resulting mixture was filtered and washed withEtOAc to give the solvent, which was concentrated in vacuoand the residue was purified by flash column chromatographyon a silica gel to give the desired product

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 Cyclohexanecarboxamide.

Reference:
Article; Zhang, Xing-Song; Zhang, Xiao-Hong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 1; (2016); p. 89 – 94;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16066-84-5, 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 16066-84-5 as follows.

To a solution of tert-butyl N-methylcarbamate (300 mg, 2.29 mmol, CAS16066-84-5) in DMF (10 mL) was added NaH (183 mg, 4.58 mmol, 60% purity) at 0 C. The mixture was stirred at 25 C. for 2 hours. Then non-8-ynyl methanesulfonate (0.5 g, 2.29 mmol, synthesized via Step 1 of Intermediate GQ) in dry DMF (2 mL) was added at 0 C., and then the mixture was stirred at 25 C. for 5 hours. On completion, the mixture was quenched by addtion H2O (30 mL), then extracted with EA (3¡Á50 mL), and the organic phase was concentrated in vacuo to give a residue. The residue was purified by flash silica gel chromatography to give the title compound (410 mg, 70% yield) as colorless oil. 1H NMR (400 MHz, DMSO-d6) delta 3.14 (t, J=7.6 Hz, 2H), 2.75 (s, 3H), 2.74-2.72 (m, 1H), 2.17-2.11 (m, 2H), 1.48-1.42 (m, 4H), 1.39 (s, 9H), 1.35-1.18 (m, 6H).

According to the analysis of related databases, tert-Butyl methylcarbamate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 22726-00-7 name is 3-Bromobenzamide, 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. 22726-00-7

Step 1: 3-(3-Bromophenyl)-1H-1,2,4-triazole (alternate reparation) A slurry of 3-bromobenzamide (77.4 g; 387 mmol) in DMF-DMA (150 mL) was prepared at room temperature and heated to 80 C. for 5 h. The mixture was cooled, poured into ice water (~2L) and stirred at room temperature 2 h. Precipitated solid was collected by filtration and washed with water (3*500 mL) and hexanes (2*200 mL), and the cake was air-dried on the filter. The above solid was added to a solution of hydrazine monohydrate (18.0 mL; 370 mmol) in acetic acid (500 mL) at room temperature (internal temp RT?~40 C. during addition). The mixture was stirred 5 min and heated to 90 C. for 90 min. The mixture was cooled, and partially concentrated in vacuo to approximately 100 mL. The mixture was poured into ice water (~3 L) and stirred 1 h. Precipitated solid was collected by filtration, washed with water and the cake was air-dried on the filter overnight. The solid was recrystallized from benzene, affording the title compound as a colorless solid. LC/MS (method E) tR 0.61 min, m/z 224, 226 (M+H Br isotopes).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromobenzamide, and friends who are interested can also refer to it.

Reference:
Patent; IGNAR, DIANE MICHELE; US2010/113512; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 112101-81-2 name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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. 112101-81-2

EXAMPLE 2: Formation of tamsulosin amide (4) A 500 ml three-necked, round bottom flask was charged with 15.12g of amine 3 and 76 mi of THF. With moderate stirring under nitrogen, a heavy white suspension was formed. The suspension was then cooled in an ice-water bath to 0- 5C. With moderate stirring, 65 ml of a 1 M solution of diisobutylaluminum hydride in THF was added to the suspension at a rate such that the batch temperature was maintained at 5-10C. After the addition was completed, the mixture was stirred at 5-10C for 5 minutes to give a light white suspension. The cooling bath was removed and the mixture was allowed to warm to 20-25C and agitated for 1 hour at this temperature. With moderate agitation, 13.02 g of 2 in toluene was charged into the mixture via a syringe. The resulting reaction mixture was stirred at 20-25C for 16 hours and then cooled in an ice-water bath to 0-5C. With vigorous agitation, HCI was charged in slowly such that the reaction temperature was maintained at 20- 25C. A heavy white suspension was formed. The above suspension was transferred to a 1 L Erlenmeyer flask equipped with a magnetic stirring bar with the aid of CH2CI2. This mixture was stirred vigorously for 30 minutes at 20-25C to give a biphasic solution. The layers were separated and the lower organic layer was collected and washed with water. The cloudy solution was filtered and concentrated via distillation under atmospheric pressure. The solution was cooled to 40-50C and ethanol was added. The resultant solution was again concentrated via distillation under atmospheric pressure to generate a heavy white suspension. The heavy white suspension obtained above was cooled to 20-25C. With moderate stirring, MTBE was charged. The resultant mixture was stirred for 5 minutes and then cooled in an ice-water bath to 0-5C. Agitation continued for another 30 minutes. The white solid in the suspension was collected by suction filtration while cold. The cake was collected and dried under vacuum at 45C for 16 hours to give 20.2 g of the amide 4 with a yield of 77%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; TORCAN CHEMICAL LTD.; WO2005/51897; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, A new synthetic method of this compound is introduced below., 107017-73-2

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (3.5 g; 18.7 mmol) and imidazole (2.54 g; 37.4 mmol) in DCM (40 mL) was added TBDPSC1 (4.11 mL;18.7 mmol). The reaction mixture was stirred for 4 h. Water (50 mL) and DCM (20 mL) were added. The two layers were separated and the aq. phase was extracted twice with DCM (2 x 25 mL). The evaporation residue was purified by CC (EA-Hept) to afford the title compound (8.85 g; >95% yield) as a colorless oil.?H NMR (d6-DMSO) oe: 7.64-7.60 (m, 4H); 7.49-7.40 (m, 6H); 7.20 (s, 1H); 3.66 (s, 2H);1.36 (br s, 9H); 1.00 (s, 9H); 0.7 1-0.65 (m, 2H); 0.64-0.60 (m, 2H).MS (ESI, mlz): 426.1 [M+Hj for C25H35NO3Si; tR = 1.11 mm.

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; ACTELION PHARMACEUTICALS LTD; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; (141 pag.)WO2017/36968; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

107017-73-2, A common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, molecular formula is C9H17NO3, 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.

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (3.5 g; 18.7 mmol)and imidazole (2.54 g; 37.4 mmol) in DCM (40 mL) was added TBDPSCl (4.11 mL;18.7 mmol). The reaction mixture was stirred for 4 h. Water (50 mL) and DCM (20 mL)were added. The two layers were separated and the aq. phase was extracted twice with25 DCM (2 x 25 mL).The evaporation residue was purified by CC (EA-Hept) to afford thetitle compound as a colourless oil (8.85 g; > 95% yield).1H NMR (d6-DMSO) o: 7.64-7.60 (m, 4H); 7.49-7.40 (m, 6H); 7.20 (s, 1H); 3.66 (s, 2H);1.36 (br. s, 9H); 1.00 (s, 9H); 0.71-0.65 (m, 2H); 0.64-0.60 (m, 2H).MS (ESI, m/z): 426.1 [M+H+] for CzsH3sN03Si; tR = 1.11 min.

The synthetic route of tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DIETHELM, Stefan; MIRRE, Azely; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; (99 pag.)WO2017/198647; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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 20348-09-8, 20348-09-8

PREPARATION B; Phenyl 3-[(diphenoxyphosphoryl)oxy]-2,3-dihydro-4H-pyrido-[3,2-b][1,4]oxazine-4-carboxylate; Step A: Phenyl 2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one-4-carboxylate; Under an anhydrous atmosphere, a solution of 10 mmol of 2H-pyrido[3,2-b][1,4]oxazin-3-one in 50 ml of tetrahydrofuran is cooled to -78 C. At that temperature, 11 mmol of a 1.6M solution of n-butyllithium in hexane are added dropwise. After 30 minutes’ contact at -78 C., 11 mmol of phenyl chloroformate are added dropwise and stirring is maintained for a further 2 hours. After returning to ambient temperature, the solution is hydrolysed and then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated. After purification by chromatography on silica gel (petroleum ether/ethyl acetate: 8/2), the expected product is isolated. Melting point: 97 C. IR (KBr): vC=O=1717 cm-1; 1803 cm-1. Mass spectrum: m/z 271 (M+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, 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Coudert, Gerard; Lepifre, Franck; Caignard, Daniel-Henri; Renard, Pierre; Hickman, John; Pierre, Alain; Kraus-Berthier, Laurence; US2006/3997; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, A new synthetic method of this compound is introduced below.

820 mg of tert-butyl N-[[4-(aminomethyl)-phenyl]-methyl]-carbamate and 421 mg of TEA was dissolved in 10 mL of DCM, cooled in an ice bath and 725 mg of thioacetic acid S-(4-chlorocarbonyl-phenyl) ester, dissolved in 5 mL of DCM, was slowly added. The mixture obtained was stirred for 30 min at rt, the phases were separated, the organic phase obtained was washed successively with 2N HCl and 5% aqueous NaHCO3 solution, dried over Na2SO4 and evaporated to dryness. The title compound was obtained in the form of pale brown crystals.

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; NABRIVA THERAPEUTICS AG; Thirring, Klaus; Heilmayer, Werner; Riedl, Rosemarie; Kollmann, Hermann; Ivezic-Schoenfeld, Zrinka; Wicha, Wolfgang; Paukner, Susanne; Strickmann, Dirk; (90 pag.)US2016/332963; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics