Tag: M.W=100-200

Electric Literature of 4424-80-0, A common heterocyclic compound, 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, molecular formula is C10H11NO, 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.

The starting material is prepared as follows: To a solution of 2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (2.5 g) in chloroform (30 ml), phosphorus pentachloride (3.2 g) was added in portions, while maintaining the temperature at 0¡ã-5¡ã. When the addition was complete, iodine (30 mg) was added followed by bromine (2.5 g), which was added dropwise over 5 minutes. The mixture was then refluxed for 4 hours. The chloroform solution was evaporated and the residue was partitioned between ice-water (30 ml) and dichloromethane (75 ml). The organic phase was dried over magnesium sulfate and evaporated under reduced pressure. The crude residue was purified by chromatography over silica gel, eluding with ether and hexane (7:3). Concentration of the appropriate fractions yielded 3-bromo-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. 146¡ã-148¡ã.

The synthetic route of 4424-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4575503; (1986); A;; ; Patent; Ciba-Geigy Corporation; US4410520; (1983); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 445-28-3, A common heterocyclic compound, 445-28-3, name is 2-Fluorobenzamide, molecular formula is C7H6FNO, 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: The appropriate amide 32a-p, benzhydrazide (40a), or p-toluenesulfonylhydrazide (43a) (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/argon re-filledthree times. Subsequently, anhyd CH2Cl2 (25 mL) was added and themixture was stirred at r.t. for 10 min before dropwise addition of oxalylchloride (3.0 mmol, 3.0 equiv) followed. The reaction mixturewas then stirred at reflux for 2.5-3.0 h before cooling to r.t. and thesolvent was evaporated in vacuo. Subsequently, the appropriate nucleophile32, 34, 36, 38, 40, 42, 43, or 45 (1.1-1.25 mmol, 1.1-1.25equiv) was rapidly added and the flask was evacuated/argon re-filledbefore anhyd toluene (12 mL) was added. The reaction mixture wasthen stirred at reflux for 2.5-3 h before cooling to r.t. and concentrationto about 1/3 of the initial volume on rotavapor. Hexane was addedto the residue and the obtained precipitate (often sonicated) wascollected by filtration under reduced pressure to yield the crudeproduct. When necessary, the isolated material was purified either bycrystallization from MeOH or flash chromatography on silica gel withhexane-EtOAc as the eluent.

The synthetic route of 445-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hernandez, Anolan Garcia; Grooms, Gregory M.; El-Alfy, Abir T.; Stec, Jozef; Synthesis; vol. 49; 10; (2017); p. 2163 – 2176;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 38267-76-4, 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. 38267-76-4, name is tert-Butyl ethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00698] Step C: 6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-((1r,4r)-4-phenoxycyclohexyl)-1H-pyrazolo[4,3-c]pyridine (25 mg, 0.061 mmol), 2-(Dicyclohexylphosphino)-2?,4?,6?-tri-i-propyl-1,1?-biphenyl (29 mg, 0.061 mmol), Cs2CO3 (80 mg, 0.25 mmol) and Pd2(dba)3 (28 mg, 0.031 mmol) were diluted with dioxane (500 muL), followed by the addition of tert-butyl ethylcarbamate (89 mg, 0.61 mmol). The reaction mixture was purged with argon, sealed and heated to 95 C. After 12 h, the reaction was partitioned between ethyl acetate and water, dried over MgSO4, filtered and concentrated. The residue was purified over silica gel (10-60% ethyl acetate/hexanes) to afford tert-butyl ethyl(3-(1-methyl-1H-pyrazol-4-yl)-1-((1r,4r)-4-phenoxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (20 mg, 0.039 mmol, 63 % yield).

The synthetic route of tert-Butyl ethylcarbamate has been constantly updated, and we look forward to future research findings.

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

Application of 98-18-0, 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. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Pyridine (1.0 mL, 12.98 mmol) was added dropwise to a mixture of 2- fluoro-4-methyl-benzoyl chloride (2.24 g, 12.98 mmol), 3-aminobenzenesulfonamide (2.235 g, 12.98 mmol) and dichloromethane (40.32 mL) at room temperature. The mixture was allowed to stir at room temperature for 2.5 hours before water (150 mL) was added. The mixture was filtered and the solid was collected by vacuum filtration. The solid was slurried with diethyl ether (30 mL) and filtered (twice). The solid was placed in a vacuum oven at 40 ¡ãC overnight to give 2-fluoro-4-methyl-N-(3-sulfamoylphenyl)benzamide (1.81 g, 45percent) as an off-white solid. ESI-MS m/z calc. 308.06, found 309.5 (M+1) +; Retention time: 1.42 minutes ( 3 minutes run ). 1H NMR (400 MHz, DMSO-d6) delta 10.61 (s, 1H), 8.32 (s, 1H), 7.89 – 7.80 (m, 1H), 7.62 – 7.51 (m, 3H), 7.39 (s, 2H), 7.24 – 7.11 (m, 2H), 2.39 (s, 3H) ppm.

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, 3-Aminobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); 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 4815-28-5 as follows. Product Details of 4815-28-5

General procedure: 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide(4a;1.5 mmol) was suspended in 10 ml butanol and benzaldehydes(5a-5m;1.0 mmol). Conc HCl (0.1 ml) was added to this reaction mixture and heated at 80 C for 12 h or until TLC confirms the completion of reaction. The solid obtained was filtered, washedwith water and dried.

According to the analysis of related databases, 4815-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Amawi, Haneen; Karthikeyan, Chandrabose; Pathak, Rekha; Hussein, Noor; Christman, Ryann; Robey, Robert; Ashby, Charles R.; Trivedi, Piyush; Malhotra, Ashim; Tiwari, Amit K.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 1053 – 1065;,
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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-N-methoxy-N-methylbenzamide

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give the title compound.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 2832-19-1, name is 2-Chloro-N-(hydroxymethyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-N-(hydroxymethyl)acetamide

The starting material was prepared as follows: 2-Chloro-N-(hydroxymethyl)-acetamide (0.342 g; 2.7 mmol), triphenylphosphine (1.1 g; 4.19 mmol) and DEAD (0.6 ml; 4.19 mmol) were added to a solution of N-acetyl-colchicinol (0.3 g; 0.84 mmol) in dichloromethane (20 ml) under argon atmosphere. The mixture was stirred at ambient temperature for 2 hours, evaporated and purified by flash chromatography eluding with ethyl acetate/dichloromethane (50/50) and dichloromethane/methanol (98/2) to give (1). Yield: 76 % MS-ESI: 485.1 [MH]+

The synthetic route of 2832-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Angiogene Pharmaceuticals Ltd; EP1140745; (2003); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1171331-39-7, The chemical industry reduces the impact on the environment during synthesis 1171331-39-7, name is 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride, I believe this compound will play a more active role in future production and life.

Example 108 Preparation of (Z)-2-Bromo-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzamide (AC95) To a stirred solution of (Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid (200 mg, 0.41 mmol) in anhydrous THF (5.0 mL) was added carbonyldiimidazole (82 mg, 0.51 mmol). The mixture was heated in a 50 C. oil bath for 1.5 h, treated with 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (109 mg, 0.057 mmol) and the resulting mixture heated to reflux for 8 h. After cooling to ambient temperature, the mixture was taken up in Et2O and washed twice with aqueous 5% sodium bisulfate (NaHSO4) (2*) and once with saturated NaCl (1*). After dying over MgSO4, concentration in vacuo and purification by medium pressure chromatography on silica with EtOAc/Hexanes as the eluents, the title compound was obtained as a white foam (160 mg, 41%) mp 48-61 C.: 1H NMR (400 MHz, CDCl3) delta 7.58 (d, J=7.9 Hz, 1H), 7.44-7.29 (m, 3H), 7.14 (dd, J=7.9, 1.6 Hz, 1H), 6.86 (d, J=11.4 Hz, 1H), 6.76 (t, J=5.9 Hz, 1H), 6.59 (br s, 1H), 6.21-6.04 (m, 1H), 4.23 (d, J=5.5 Hz, 1H), 3.98 (qd, J=9.0, 6.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -69.31, -72.3; EIMS m/z 626.9 ([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, 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171314; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 96-30-0, A common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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.

A suspension of Intermediate 7 (500 mg, 1.48 mmol), K2C03 (204 mg, 1.48 mmol) and potassium thioacetate (590 mg, 5.16 mmol) in DMF (5.5 mL) was heated at 140C under microwave irradiation for 3 h. After cooling, the mixture was dissolved in water (20 mL), neutralized to pH 6 with 1M HCl and extracted with EtOAc (3 x 50 mL). The organic layer was washed with saturated brine (3 x 30 mL), dried (MgS04) and concentrated in vacuo. Purification by column chromatography on silica, eluting with 5% EtOAc in DCM, gave a yellow solid (127 mg, 26%). LCMS (ES+) 337 (M+H)+. A suspension of this solid (114 mg, 0.339 mmol), K2C03 (46.8 mg, 0.339 mmol) and 2- chloro-N-methylacetamide (87 mg, 0.809 mmol) in DMF (3 mL) was heated at 120C under microwave irradiation for 1 h. After cooling, the mixture was dissolved in a 1 : 1 mixture of EtOAc and Et20 (150 mL) and washed with saturated brine (3 x 30 mL). The organic layer was dried (MgS04) and concentrated in vacuo. Purification by column chromatography on silica, eluting with 40% EtOAc in DCM, gave a white solid (119 mg, 86%). LCMS (ES+) 408 (M+H)+. This solid (119 mg, 0.292 mmol) was dissolved in DCM (7.6 mL) and TFA (1.33 mL) was added. The reaction mixture was stirred at r.t. for 1.5 h and concentrated in vacuo. The residue obtained was basified with 0.8M aqueous NaOH (8 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were dried (MgS04) and concentrated in vacuo to give a colourless glass (117 mg, 100%). LCMS (ES+) 308 (M+H)+. A solution of this material (117 mg, 0.292 mmol), 2,4-dichloro-5-cyanopyrimidine (76.2 mg, 0.438 mmol) and DIPEA (0.20 mL, 1.168 mmol) in THF (2 mL) was stirred at r.t. for 4 h. The mixture was dissolved in EtOAc (150 mL) and washed with saturated brine (3 x 30 mL). The organic layer was dried (MgS04) and concentrated in vacuo. Purification by column chromatography on silica, eluting with DCM/MeOH NH3 solution in MeOH (98: 1 :1), gave a pale brown foam (105 mg, 81%). LCMS (ES+) 445, 447 (M+H)+ (mixture of regioisomers). A solution of this material (105 mg, 0.236 mmol) in a mixture of 7M NH3 solution in MeOH (2 mL) and NH4OH (1 mL) was heated at 120C under microwave irradiation for 1 h. After cooling, the mixture was dissolved in saturated brine (40 mL) and extracted with EtOAc (3 x 100 mL). The organic layer was dried (MgS04) and concentrated in vacuo. Purification by preparative HPLC afforded the title compound (13.2 mg, 13%) as an off-white solid, delta? (DMSO-d6) 8.31 (1H, s), 8.25 (1H, s), 8.15 (1H, d, J5.33 Hz), 7.87-7.81 (2H, m), 7.40 (1H, t, J9.13 Hz), 7.15 (1H, br s), 6.97 (1H, br s), 5.55-5.46 (1H, m), 4.10 (1H, d, J 15.2 Hz), 4.04 (1H, d, J 15.2 Hz), 2.65 (3H, d, J4.59 Hz), 2.58 (3H, s), 1.61 (3H, d, J 6.82 Hz). LCMS (ES+) 426 (M+H)+, T 3.37 minutes {Method 1).

The synthetic route of 96-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; RAPHY, Gilles; BUeRLI, Roland; HAUGHAN, Alan, Findlay; WO2011/58113; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 121492-06-6, These common heterocyclic compound, 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, 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.

Example 128: N-{5-[3-(4-Bromo-2-fluoro-phenylamino)-pyridin-4-yl]- [1 ,3,4]oxadiazol-2-yl}-N’-methyl-ettiane-1 ,2-diamine; Step 1 : 5-[3-(4-Bromo-2-fluoro-phenylamino)-pyridin-4-yl]-3H-[1 ,3,4]oxadiazol-2-one (example 19, 100mg, 0.277mmol) was dissolved in ethanol (3ml), N-(2-aminoethyl)-N – methylcarbamic acid ^-butylester (96rng, 0.554mmol) was added and the mixture was stirred for20min at 1500C in a microwave oven. The volatiles were removed to give the crude compound, which was used in the next step.Step 2: Dry dichloromethane (5ml) was added to the product derived from step 1 followed by triphenylphosphine (113rng, 0.429mmol), triethylamine (58mul, 0.416mmol) and carbon tetrachloride (107mul, 1.11 mmol). The mixture was heated at 1000C for20min in a microwave oven, the volatiles were removed and the crude material was purified by preparative HPLC to give 87mg (62/yield) of the Boc-protected title compound. The material was treated with 4N HCI in dioxane (4ml) for 1h at ambient temperature and the volatiles were removed to give the pure title compound. LC-MS (method V): rt = 1.94rnin; m/z [M+ H]+ 407/409.

The synthetic route of 121492-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics