Month: March 2021

Application of 19962-04-0,Some common heterocyclic compound, 19962-04-0, name is 3-Aminophenyl dimethylcarbamate, molecular formula is C9H12N2O2, 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.

C. Preparation of tert-butyl 4-(2-(dimethylamino)ethyl)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate. 1-(tert-Butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acid from step B (100 mg, 0.33 mmol), HATU (175 mg, 0.46 mmol), and N,N-diisopropylethylamine (0.116 mL, 0.67 mmol) were stirred in isopropyl acetate for 10 minutes. 3-aminophenyl dimethylcarbamate (90 mg, 0.5 mmol) was added, and the reaction was stirred at 85 C. for 2 hours, cooled to room temperature, stirred overnight, and then diluted with EtOAc, washed with sat. aq. Na2CO3 and brine (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum, to give the title compound as a viscous oil. MS (ES+) [M+H]+=463.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Aminophenyl dimethylcarbamate, its application will become more common.

Reference:
Patent; Burgoon, Hugh Alfred; Goodwin, Nicole Cathleen; Harrison, Bryce Alden; Healy, Jason Patrick; Liu, Ying; Mabon, Ross; Marinelli, Brett; Rawlins, David Brent; Rice, Dennis Stewart; Whitlock, Norris Andrew; US2009/264450; (2009); A1;,
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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 35303-76-5 as follows. Safety of 4-(2-Aminoethyl)benzenesulfonamide

DCE (20 mL) in 4- (2-aminoethyl)benzenesulfonamide(110mg, 0.55mmol), AcOH (0.10mL) and tert- butyl 2- (2-formyl -1H-imidazol-1-yl) acetic acid (250mg, 1.19mml) a solution containing the mixturewas stirred for 30 minutes at 80 under nitrogen. The reaction mixture was cooled to 0 , and treated with NaBH (OAc) 3 (3.165g,15mmol). The reaction mixture was stirred at room temperature overnight anddecomposed with water. The reaction mixture was extracted with DCM. The organiclayer was dried and concentrated in vacuo. The residue was purified by flashchromatography on silica gel, tert-butyl 2,2 ‘- (2,2’ – (4-sulfamoyl-phenethylaza screw-yl) bis (methylene) bis (lH-imidazole-2,1 diyl)) resulted diacetate(132mg, 41percent).

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MOLECULAR INSIGHT PHARMACEUTICALS INCORPORATED; BABICH, JOHN W; (133 pag.)JP5856247; (2016); B2;,
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. 195314-59-1, name is tert-Butyl (4-aminocyclohexyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 195314-59-1

To a cooled (0C) solution of cyanuric chloride (1 eq.) in THF and DIPEA is added dropwise, (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (2 eq.) in THF. After stirring at RT for 1 hour, the solvent is removed in vacuo and the product is partitioned between DCM and 2 M HCl. The organic portion is separated, washed with water, brine, dried (MgSO4) and concentrated in vacuo to yield Intermediate IAl which is used in the next step without further purification.

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/121924; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 25216-74-4, name is tert-Butyl (3-bromophenyl)carbamate, 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. Application In Synthesis of tert-Butyl (3-bromophenyl)carbamate

19 g (475 mmol) of sodium hydride (60% in oil) are added.in small amounts to a solution of 114 g (447 mmol) of tert-butyl (3-bromobenzyl) carbamate in 800 ml of dimethylformamide and the reaction medium is stirred until evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is maintained for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated by settling, dried over magnesium sulphate and evaporated. 115 g of tert-butyl (3-bromobenzyl)-N-methylcarbamate are obtained. Yield = 95%.

The synthetic route of tert-Butyl (3-bromophenyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2005/108352; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 456-64-4, 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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a-78 C solution of Preparation 30 (7.0 g, 19.1 mmol) in THF (80 mL) add potassium hexamethyldisilane (KHMDS) (53 mL, 0.5 M solution in toluene, 26.7 mmol) over 5 min. Add hexamethylphosphoramide (HMPA) (4.64 mL, 26.7 mmol) quickly, and stir the solution at-78 C for 25 min. Add a solution of N-phenyl triflamide (11.5 g, 32.2 mmol) in THF (15 mL + rinse) via syringe. Maintain the resulting solution at-78 C for 2 h, then pour the reaction contents into 1/2 SATD. NAHCO3 AND extract with ET20 (150 ML) and EtOAc (2 x 75 mL). Wash the combined organic extracts with H2O (2 x 100 mL) and brine (100 mL), dry over NA2SO4, and concentrate. Purification of the crude product by MPLC (0 to 12 to 25% EtOAc/hexanes) affords Preparation 31 (6.25 g, 66%) as an OFF-WHITE SOLID. H NMR (CDC13) 8 7.25-7. 43 (m, 5 H), 6. 84 (d, J = 8.8 Hz, 1 H), 6. 80 (dd, J = 8.8, 2.8 Hz, 1 H), 6.72 (d, J = 2. 8 Hz, 1 H), 5.02 (s, 2 H), 4.04 (m, 4 H), 3. 82 (dd, J = 4.4, 12. 8 Hz, 1 H), 2.66 (dq, J = 14.0, 2.4 Hz, 1 H), 2.21 (m, 2 H), 1.91 (m, 1 H), 1. 80 (t, J = 12.8 Hz, 1 H), 1.64 (TD, J = 12.8, 4.4 Hz, 1 H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94400; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 227940-71-8, 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 227940-71-8 as follows.

Example 8: Synthesis of 3,7-diazabicyclo[3.3.1]nonane-3-carboxyIic acid tert-butyl esterExample 8 relates to the synthesis of 3,7-diazabicyclo[3.3.1]nonane-3- carboxylic acid tert-butyl ester (or N-(tert-butoxycarbonyl)-3,7- diazabicyclo[3.3.1]nonane), which was prepared according to the following techniques:7-Benzyl-3,7-diazabicyclo [3.3.1 ] nonane-3-carboxylic acid tert-butyl ester (or N-benzyl-N’-(tert-butoxycarbonyI)-3,7- diazabicyclo[3.3.1]nonane); 7-Benzyl-3,7-diazabicyclo [3.3.1] nonane-3-carboxylic acid tert-butyl ester was prepared according to procedures set forth by Stead et al. in Org. Lett. 7(20): 4459 (2005).3,7-Diazabicyclo[3.3.1]-3-carboxyIic acid tert-butyl ester 7-Benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester(0.49 g, 1.6 mmol) was dissolved in methanol (20 mL) and 20% Pd(OH)2/C (wet) (~ 2 g) was added under a nitrogen atmosphere. This mixture was warmed to about 5O0C and shaken for 2 h under 55 psi of hydrogen. The resulting mixture was EPO filtered and concentrated to give 0.32 g (94% yield) of the title compound (MS m/z 227 (M+H)).

According to the analysis of related databases, 227940-71-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TARGACEPT, INC.; WO2008/57938; (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 96-30-0 as follows. Quality Control of 2-Chloro-N-methylacetamide

Ethyl 1-((6-hydroxyquinolin-4-yl)thio)cyclobutanecarboxylate 5a (50 mg, 0.17 mmol), 2-chloro-N-methylacetamide (50 mg, 0.17 mmol) and potassium carbonate (35 mg, 0.25 mmol) were added to 4 mL of N,N-dimethylformamide, successively. Upon completion of the addition, the reaction solution was heated to 60 C. and stirred for 3 hours, followed by addition of 20 mL of water, and extraction with ethyl acetate (30 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound ethyl 1-((6-(2-(methylamino)-2-oxoethoxy)quinolin-4-yl)thio)cyclobutanecarboxylate 14a (40 mg, a brown oil), yield: 65%. MS m/z (ESI): 373.3 [M-1]

According to the analysis of related databases, 96-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Lt.d; PENG, Jianbiao; SUN, Piaoyang; LAN, Jiong; GU, Chunyan; LI, Xiaotao; LIU, Bonian; HAN, Chunzhou; HU, Qiyue; JIN, Fangfang; DONG, Qing; CAO, Guoqing; (57 pag.)US2016/108035; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, 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 711007-44-2, Quality Control of 2,3-Diaminobenzamide

To a 100 ml three-neck flask was added 2,3-diaminobenzamide (3.2 g, 20 mmol), compound A (3.85 g, 22 mmol), sulfur powder (3.2 g, 100 mmol) was added, and stirred at 170 C. After 6 h, after cooling, 60 ml of methylene chloride was added and dissolved. The silicon gel was mixed and concentrated on a silica gel column. Chromatography on a silica gel column gave the desired product (C1) in a yield of 1.28 g (yield: 20%).

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, 2,3-Diaminobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong University Qilu Hospital; Tan Bingxu; (9 pag.)CN107556288; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1015-89-0, These common heterocyclic compound, 1015-89-0, name is Phenanthridin-6(5H)-one, 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.

Phenanthridin-6(5H)-one (1; 0.100 g, 0.492 mmol) was placed in aSchlenk flask under argon. POCl3 (3.29 g, 2 mL, 21.4 mmol, 43 equiv)was added, and the mixture was stirred at 100 C for 24 h. The mixturewas cooled, poured onto ice, and stirred for 15 min. The solidthat formed was collected by filtration, washed thoroughly with H2O,and dried in vacuum to give a light-brown solid; yield: 95.5 mg (87%);Rf = 0.65 (hexane-EtOAc, 5:1; detection: UV).IR (KBr): 3103, 3072, 3039, 1613, 1574, 757 cm-1.1H NMR (600 MHz, acetone-d6): delta = 7.69 (ddd, J = 8.2, 7.0, 1.4 Hz, 1 H,H-12), 7.75 (ddd, J = 8.2, 7.0, 1.5 Hz, 1 H, H-13), 7.77 (ddd, J = 8.2, 7.0,1.2 Hz, 1 H, H-4), 7.91 (ddd, J = 8.3, 7.0, 1.3 Hz, 1 H, H-5), 8.10 (ddd,J = 8.2, 1.4, 0.6 Hz, 1 H, H-14), 8.48 (ddd, J = 8.2, 1.3, 0.6 Hz, 1 H, H-3),8.54 (ddt, J = 8.3, 1.5, 0.6 Hz, 1 H, H-11), 8.62 (ddt, J = 8.3, 1.2, 0.3 Hz, 1H, H-6).13C NMR (151 MHz, acetone-d6): delta = 151.45 (C-2), 143.31 (C-8),134.51 (C-10), 131.77 (C-5), 129.36 (C-13), 129.32 (C-14), 128.25 (C-4), 127.74 (C-3), 127.49 (C-12), 124.90 (C-9), 124.03 (C-7), 122.28 (C-6), 122.21 (C-11). MS (ESI): m/z (%) = 214.1 [M + H]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C13H9ClN: 214.0148; found:214.0149.

Statistics shows that Phenanthridin-6(5H)-one is playing an increasingly important role. we look forward to future research findings about 1015-89-0.

Reference:
Article; Sonawane, Manoj R.; Vavra, Jan; ?aman, David; Cisa?ova, Ivana; Teply, Filip; Synthesis; vol. 47; 22; (2015); p. 3479 – 3488;,
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Synthetic Route of 38267-76-4, A common heterocyclic compound, 38267-76-4, name is tert-Butyl ethylcarbamate, molecular formula is C7H15NO2, 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.

Ethylamine hydrochloride (2.81 g, 34.5 mmol) and triethylamine (14.4 mL, 103 mmol) were dissolved in CH2Cl2 (100 mL), and cooled on ice. A solution of di-t-butyl dicarbonate (7.69 g, 35.2 mmol) in CH2Cl2 (15 mL) was added, and stirred at room temperature for 14.5 h. The mixture was diluted with CH2Cl2, washed twice with 5% aqueous HCl solution, once with saturated aqueous NaHCO3 solution,dried over anhydrous magnesium sulfate, and evaporated to give crude t-butyl ethylcarbamate (4.36 g, 87%). Crude t-butyl ethylcarbamate (3.77 g, 26.0 mmol) and allyl bromide (4.5 mL, 52.0 mmol) were dissolved in DMF (87 mL), and cooled on ice. NaH (60% in oil, 2.23 g, 55.8 mmol) was added, and stirred at room temperature for 4.5 h. After cooled on ice, the reaction was quenched by adding water. The mixture was diluted with Et2O, washed with 5% aqueous Na2S2O3 solution and saturated aqueousNaHCO3 solution, dried over anhydrous magnesium sulfate, and evaporated. Purification by column chromatography (n-hexane : EtOAc = 30 : 1 v /v), and distillation (3.0 kPa, 89 C) gave 42d (1.73 g, 36%) as colorless liquid. 1HNMR (400 MHz, CDCl3) delta 1.08 (t, J = 7.2 Hz, 3H), 1.46 (s, 9H), 3.05 (br, 2H), 3.70~3.90 (br, 2H). 13CNMR (100 MHz, CDCl3) delta 13.45, 28.43, 49.06, 79.22, 115.92, 155.37. IR (neat) 2976, 1698 cm-1.

The synthetic route of 38267-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Honzawa, Shinobu; Uchida, Mitsuaki; Tashiro, Takuya; Sugihara, Takumichi; Heterocycles; vol. 95; 2; (2017); p. 994 – 1029;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics