Tag: M.W=100-200

Reference of 154748-63-7, A common heterocyclic compound, 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)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.

General procedure: To a solution of tert-butyl (1S,3R)-3-hydroxycyclopentylcarbamate (0.50g, 2.5mmol),4-(trifluoromethyl)phenol (0.49g, 3mmol) and triphenylphosphine (0.98g, 3.75mmol) in anhydrous THF (8mL) was dropwise added DIAD (0.98mL, 4.68mmol) in anhydrous THF (7mL). The reaction solution was stirred at room temperature overnight. The resulting solution was concentrated in vacuo, and the residue was subjected to flash column chromatography on silica gel (eluting with EtOAc-heptane by a gradient of EtOAc from 4% to 32%) to deliver title compound as colorless crystals (0.63g, 73%)

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:
Article; Aktas, Bertal H.; Bohm, Andrew; Chorev, Michael; Du, Ronghui; Halperin, Jose; Reis Monteiro dos Santos, Guilherme Rodrigo; Yefidoff-Freedman, Revital; Zhang, Qingwen; European Journal of Medicinal Chemistry; vol. 187; (2020);,
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Electric Literature of 4141-08-6, 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. 4141-08-6, name is 2-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.

The synthetic route of 2-Amino-N-methylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun; Heterocycles; vol. 94; 1; (2017); p. 86 – 94;,
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Some common heterocyclic compound, 1120-16-7, name is Dodecanamide, molecular formula is C12H25NO, 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. Computed Properties of C12H25NO

A flask was charged with N-(7-chloro-7,8-dihydro-1,8- naphthyridin-2yl)dodecanamide (6) (15.6 g, 42.8mmol), dodecanamide (10.3 g, 51.3mmol), Pd(OAc)2 (593 mg, 2.6 mmol), Xantphos (3.3 g, 5.8mmol), K2CO3 (5.9 g, 42.8mmol), and dry dioxane (250 mL). Oven-dried molecular sieves (4) were added and the mixture was stirred overnight at room temperature under Ar. Subsequently, the mixture was heated to 80 C and stirred overnight under Ar. After cooling to room temperature, the mixture was filtered and the residue was rinsed with CHCl3. Recrystallization in ethanol and purification by flash chromatography (80% CHCl3/20% EtOAc) yielded the product as a white solid (16.5 g, 73%). 1HNMR (400 MHz, CDCl3): 8.42 (d, 2H, J = 8.8 Hz, Ar), 8.14 (d, 2H, J = 8.8 Hz, Ar), 8.12 (bs, 2H, NH), 2.47 (t, 4H, J = 7.6 Hz, O=C-CH2), 1.56 (m, 4H, J = 8.0, 7.6 Hz, O=C-CH2-CH2), 1.26 (m, 32H, alkyl-CH2), 0.88 (t, 6H, alkyl-CH3). 13CNMR (100 MHz, CDCl3): 172.2, 153.74, 138.98, 113.34, 110.01, 76.75, 38.13, 31.90, 29.60, 29.44, 29.33, 29.15, 25.29, 22.68, 14.12. MALDI-ToF MS: calculated for C32H52N4O2 524.78, observed m/z 525.43 [M + H+], 1087.79 [dimer + K+]. Elemental analysis: calculated for C32H52N4O2: C, 73.24; H, 9.99; N, 10.68; O, 6.10%. Found: C, 73.35; H, 9.59; N, 10.26%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1120-16-7, its application will become more common.

Reference:
Article; Teunissen, Abraham J.P.; Van Der Haas, Roy J.C.; Vekemans, Jef A.J.M.; Palmans, Anja R.A.; Meijer; Bulletin of the Chemical Society of Japan; vol. 89; 3; (2016); p. 308 – 314;,
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Related Products of 354-38-1,Some common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, molecular formula is C2H2F3NO, 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 enynones (2) (0.50 mmol), trifluoroacetamide (1) (100 mg, 0.88 mmol), RuCl2(bpy)3 (9.6 mg, 0.015 mmol, 0.030 equiv), Na2CO3 (53 mg, 0.50 mmol, 1.0 equiv), and 1,2-dichloromethane (5.0 mL) were added to a reaction tube equipped with a stir bar. The tube was then exposed to blue LEDs irradiation at room temperature in air with stirring for 8 h. After the reaction was completed, the reaction mixture was extracted with 1,2-dichloromethane (30 mL),and washed with water (30 mL). The organic phase was dried with MgSO4 and evaporated in vacuo after filtration. The resulting residue was purified by column chromatography on silica gel to give the desired products 3.

The synthetic route of 354-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Taotao; Wu, Wei; Weng, Zhiqiang; Tetrahedron; vol. 75; 51; (2019);,
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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 98-18-0 as follows. category: amides-buliding-blocks

Scheme A[00230] A flask was charged with 3-aminobenzene sulfonamide (3.3 g, 19 mmol), and 20 mL of 1:1 acetone .1H2O. The solution was stirred at room temperature until the aminobenzene sulfonamide had dissolved. The flask was then cooled in an ice bath and dimethylamino-acetyl chloride HCl (4.6 g, 29 mmol) was added. To the resulting slurry sodium bicarbonate (4.8 g, 57 mmol) was added over a 15 m period. After 30 min the reaction was removed from the ice bath and allowed to stir at room temperature for 15 h. The reaction mixture was then filtered and washed with methanol and acetonitrile. The filtrate was dried on a rotary evaporator to yield 2-(dimethylamino)-JV-(3-sulfamoyl- phenyl)acetamide, which was submitted to the next step without further purification. MS (EI) m/z C10H15N3O3S: 258.0

According to the analysis of related databases, 98-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; WO2007/44729; (2007); A2;,
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Electric Literature of 107017-73-2, 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. 107017-73-2 name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)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.

8.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/305102; (2010); A1;,
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Related Products of 5472-37-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5472-37-7, name is N-(2-Amino-4-methoxyphenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

[023] Water (20 ml.), potassium hydroxide (6. 5 gm.), ethanol (7 ml.) & carbon DISULFIDE (7 ML. ) ARE ADDED TO THE AMINO ACETANILIDE (9.0 GM. ). SLOWLY THE REACTION mixture is heated to 80-90C & maintained for 8-10 hours. The reaction mixture is COOLED TO 10-15C. CONC. HYDROCHLORIC ACID SOLUTION (9 ML. ) IS ADDED TO REACTION mass to precipitate the product. The crude product is purified by acid base treatment to obtain pure 2-mercapto-5-methoxy benzimidazole. The yield of the product is 8 gm.

The chemical industry reduces the impact on the environment during synthesis N-(2-Amino-4-methoxyphenyl)acetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IPCA LABORATORIES LIMITED; WO2004/92142; (2004); A1;,
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Reference of 14658-93-6, These common heterocyclic compound, 14658-93-6, name is 2-Hydroxy-N,N-dimethylacetamide, 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 9.2 (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-((R)-2-dimethylcarbamoylmethoxycarbonyl-pyrrolidin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate 25 mg (0.08 mmol) TBTU and 11 muL (0.08 mmol) triethylamine were added to a solution of 50 mg (0.07 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-((R)-2-carboxy-pyrrolidin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 1 mL DMF and stirred for 10 min at RT. 8.1 mg (0.08 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added to the reaction mixture and this was shaken overnight at RT. After filtration through a syringe filter the reaction solution was purified by HPLC without further working up. The fractions containing the product were combined and freeze-dried. Yield: 38 mg (68% of theory) ESI-MS: (M+H)+=820/822 (Cl)

The synthetic route of 14658-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mueller, Stephan Georg; Rudolf, Klaus; Lustenberger, Philipp; Schaenzle, Gerhard; Santagostino, Marco; Stenkamp, Dirk; Arndt, Kirsten; Doods, Henri; US2007/49581; (2007); A1;,
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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. 88-96-0, name is Phthalamide, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O2

To a solution of (S)-tert-butyl 4-(3-(l-hydroxyethyl)benzyl)piperazine-l- carboxylate (480 mg, 1.50 mmol) in 10 mL of anhydrous THF at 00C under a positive pressure of N2 were added phthalimde (330 mg, 2.25 mmol), triphenyl phosphine (590 mg, 2.25 mmol) and DIAD (440 DL, 2.25 mmol). The solution was warmed up to ambient temperature and stirred 1 h. The solvent was removed at reduced pressure and the residue was purified by reverse-phase HPLC to afford (S)-rerr-butyl 4-(3-(l-(l,3-dioxoisoindolin-2- yl)ethyl)benzyl)piperazine-l-carboxylate as 490 mg of a white solid.

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; CYTOKINETICS, INC.; WO2007/89336; (2007); A2;,
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Some common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, molecular formula is C8H16ClNO2, 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. SDS of cas: 116861-31-5

[2-Amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone (?A64?) [0665] 100 mg of [2-amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone are dissolved in 3 ml of tetrahydrofuran together with 90 mg of tert-butyl (3-chloropropyl)carbamate. 2 ml of sodium hydroxide solution (32%) and 2 mg of tetrabutylammonium iodide are added, and the mixture is stirred at 80 C. for 16 h. The mixture is extracted 3 times with 5 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness, the residue is taken up in 3 ml of dichloromethane, and 1 ml of 4N HCl in dioxane is added. After 1 h at 25 C., the mixture is evaporated to dryness in vacuo and purified by chromatography (reversed phase HPLC). [0666] Yield: 18 mg (16%) of {2-amino-6-[2-(3-aminopropoxymethyl)-4,5-difluorophenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone; [0667] LC-MS retention time: 1.66 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116861-31-5, its application will become more common.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; Eggenweiler, Hans-Michael; Sirrenberg, Christian; Buchstaller, Hans-Peter; US2013/178443; (2013); A1;,
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