Month: February 2021

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. 185619-66-3, name is tert-Butyl (3-ethynylphenyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C13H15NO2

Step b) [3-(4-Difluoromethoxy-phenylethynyl)-phenyl]-carbamic acid tert-butyl ester A mixture of (3-ethynyl-phenyl)-carbamic acid tert-butyl ester (14.7 g, 67.7 mmol), 1-difluoromethoxy-4-iodo-benzene (18.2 g, 67.7 mmol), NEt3 (47 mL, 338 mmol), acetonitrile (225 mL), CuI (1.29 g, 6.77 mmol), and Pd(PPh3)2Cl2 (2.85 g, 4.05 mmol) was heated to 60 C. for 1 h. The reaction was diluted with EtOAc/Hex (1:10) and then passed through a pad of silica gel and concentrated and purified with chromatography using hexanes/ethyl acetate (10:1) as the eluding solvents gave the title compound (24.3 g, 100%), characterized by NMR and mass spectral analyses.

The synthetic route of 185619-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)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 107017-73-2, category: amides-buliding-blocks

Example 117A tert-butyl 1-(bromomethyl)cyclopropylcarbamate A mixture of tert-butyl 1-(hydroxymethyl)cyclopropylcarbamate (CASNo.107017-73-2; 5 g, 26.7 mmol), triphenylphosphine (9.5 g, 36.2 mmol), and carbon tetrabromide (11.9 g, 35.9 mmol) in ether (120 mL) was stirred at room temperature for 24 hours. After this time, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel (0 to 10% ethyl acetate-CH2Cl2, eluant) to afford the titled compound as a white solid, 3.594 g (54%). 1H NMR (300 MHz, CDCl3) delta ppm 5.11 (br, 1H), 3.58 (s, 2H), 1.45 (s, 9H), 1.07 (m, 2H), 0.91 (m, 2H); MS (DC) m/z 250/252 (M+H+; 79Br/81Br).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AbbVie Inc.; Altenbach, Robert J.; Liu, Huaqing; Clapham, Bruce; Aguirre, Ana L.; Cowart, Marlon; Koenig, John R.; Sarris, Kathy; Scanio, Marc J.; Swinger, Kerren K.; Vasudevan, Anil; Villamil, Clara I.; Woller, Kevin R.; (95 pag.)US9777020; (2017); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 120-66-1, A common heterocyclic compound, 120-66-1, name is N-(o-Tolyl)acetamide, molecular formula is C9H11NO, 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 solution of phosphoryl trichloride (62.4 ml_, 700.0 mmol) in N,N- dimethylformamide (19.2 ml_, 250.0 mmol) was cooled to 0 0C and stirred for 30 min under nitrogen. To this solution N-O-tolylacetamide (14.9 g, 100.0 mmol) was added at 20 0C and the resulted mixture was stirred for 30 min under nitrogen. The temperature of the reaction mixture was slowly raised to 80 0C and stirred for 20 h under nitrogen. Yellow solid precipitated out upon slow addition of crushed ice (300 g) to the reaction mixture. The resulting solid was filtered, washed with water and dried under high vacuum at 60 0C to afford 2-chloro-8-methylquinoline-3-carbaldehyde (7.61 g, 37%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 10.36 (s, 1 H), 8.92 (s, 1 H), 8.08 (d, J = 8.1 Hz, 1 H), 7.82 (d, J = 6.9 Hz, 1 H), 7.61 (t, J = 7.6 Hz, 1 H), 2.65 (s, 3H).

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; XENON PHARMACEUTICALS INC.; WO2008/113006; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 137618-48-5, 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. 137618-48-5, name is tert-Butyl (2,3-dihydroxypropyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-[(tert-butyloxycarbonyl)amino]propane-2,3-diol (example 17a) (3.88 g, 20 mmol) was dissolved in toluene (250 ml). Imidazole (1.73 g, 25 mmol), triphenylphosphine (6.65 g, 25 mmol) and iodine (5.15 g, 20 mmol) were then added in that order. The reaction medium was stirred at room temperature for 17 hours and 0.5 equivalents of imidazole, triphenylphosphine and iodine were added. After 21 hours of reaction, a saturated sodium sulfite solution was added until complete blanching of the reaction medium. The phases were allowed to settle and the aqueous phase was extracted twice with toluene. The combined organic phases were washed with saturated sodium chloride solution, dried on magnesium sulfate, filtered and the solvent evaporated. The residue obtained (11.02 g) was purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 95:5) to give the desired compound as a yellow paste which was promptly used in the next reaction. Yield: 41% Rf (dichloromethane/methanol 98:2): 0.24 IR: nuNH amide 3387 cm-1; nuCO carbamate 1678 cm-1

The synthetic route of tert-Butyl (2,3-dihydroxypropyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Darteil, Raphael; Caumont-Bertrand, Karine; Najib, Jamila; US2006/69156; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 67341-01-9, These common heterocyclic compound, 67341-01-9, name is tert-Butyl (2-hydroxy-1-phenylethyl)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.

N-Boc-D-phenylglycinol (5.0 kg), triethylamine (3.55 L), and dimethylformamaide (10.54 L) were charged to a reactor, agitated, and the mixture was cooled to 0 0C. Methanesulfonyl chloride (1.79 L) was charged through a dip-tube while maintaining the temperature below 5 0C. After completion of the reaction, acetone (15.0 L) was charged to the reactor while maintaining temperature below 5 0C. Water (12.0 L) was charged to the mixture over 3 hr, maintaining temperature below 5 0C, during which time crystallization occurred. An additional portion of water (18 L) was added while maintaining the temperature below 5 0C. The mixture was filtered and the cake was washed with 2:1 (v/v) water: acetone three times (2 x 10 L, 1 x 6600 L) and dried between 25- 40 0C under vacuum to provide methanesulfonic acid (S)-3-tert- butoxycarbonyl-amino-3-phenyl-propyl ester Id (6.278 kg, 94.5% molar yield) as a white solid. LCMS (ESI) m/z 216.0 (M-100(Boc)H+)

Statistics shows that tert-Butyl (2-hydroxy-1-phenylethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 67341-01-9.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2009/62087; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, 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 37073-15-7, category: amides-buliding-blocks

To a solution of 2-(4-fluorophenyl)acetonitrile (2 g, 15 mmol) in DMSO (15 mL) at 8 C was added t-BuOK (2.84 g, 29 mmol). The mixture was stirred for 10 min and a solution of compound 6-1 (2.92 g, 15 mmol) in DMSO (40 mL) was then added slowly via an addition funnel. The reaction mixture was warmed to RT and stirred overnight, quenched with water, and neutralized with saturated aq. NH4C1. The mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, brine, dried over MgS04, and filtered. The filtrate was concentrated and purified by silica gel column chromatography (PE/EtOAc = 5: 1) to give 6-2.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; KAELIN, David Earl, Jr.; SCOTT, Jack, D.; WU, Wen-Lian; BURNETT, Duane, A.; WO2014/99794; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 120157-97-3, 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. 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium hydride (60% in mineral oil, 134 mg, 3.35 mmol) was added portionwise to a solution of 1,1-dimethylethyl [2-(4-bromophenyl)ethyl]carbamate (for a preparation see Intermediate 99) (914 mg, 3.04 mmol) in tetrahydrofuran (THF) (25 mL). The reaction mixture was stirred at room temperature for 15 min, then methyl iodide (0.952 mL, 15.22 mmol) was slowly added to the mixture which was stirred under nitrogen for a further 2 h. An extra portion of methyl iodide (0.952 mL, 15.22 mmol) was then added to the mixture which was stirred at the same temperature for 2 more hours before being treated with methanol (1 mL). Most of the solvent was removed in vacuo and the residue partitioned between AcOEt (50 mL) and water (30 mL). The layers were separated and the aqueous phase was extracted with AcOEt (20 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 5 to 15% AcOEt in Hexanes) gave 1,1-dimethylethyl [2-(4-bromophenyl)ethyl]methylcarbamate (566 mg, 1.801 mmol, 59%) as a colourless oil. LCMS (method G): Retention time 1.35 min, [M+H]+=315.9 (1 Br)

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, N-Boc-2-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 122848-57-1,Some common heterocyclic compound, 122848-57-1, name is tert-Butyl 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate, molecular formula is C10H18N2O2, 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 10 mL microwave reaction vessel compound 5-chloro-6-ethyl-2- (pyrido[3,2-b]pyrazin-7-ylthio)-7H-pyrrolo[2,3-d]pyrimidin-4-yl 4-methylbenzenesulfonate (Example 19) (0.02 g, 0.039 mmol) and tert-butyl 3,6-diazabicyclo[3.2.0]heptane-6- carboxylate (7.7 mg, 0.039 mmol) was dissolved in ethanol (0.1 mL). The reaction was sealed and heated to 100C for 0.5 h after which the solvent was removed and the crude was used for the next step without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate, its application will become more common.

Reference:
Patent; TRIUS THERAPEUTICS, INC.; CREIGHTON, Chris; TARI, Les; CHEN, Zhiyong; HILGERS, Mark; LAM, Thanh; LI, Xiaoming; TRZOSS, Michael; ZHANG, Junhu; FINN, John; WO2011/32050; (2011); A2;,
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. 597563-17-2, name is tert-Butyl (1-(3-bromophenyl)cyclopropyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 597563-17-2

Step 2. [1-(3-Pyrazol-1-yl-phenyl)-cycIopropyl]-carbamic acid tert-butyl ester (4).This was prepared according to the literature: Antiila, J. C. et al. J. Org. Chem. 2004, 69, 5578-5587. A mixture of 1.49 g (4.8 mmol, 1.0 eq) of 1 , 0.49 g (7.2 mmol, 1.5 eq) of 2, and 1.61 g (11.7 mmol, 2.4 eq) of K2CO3 in 6.5 mL of dry toluene was prepared. While stirring, 0.15 mL (0.95 mmol, 0.20 eq) of 3 and 0.10 g (0.52 mmol, 0.11 eq) of CuI was added. The mixture was purged with N2 and was heated in a sealed vessel at 110 C for 20 h. After cooling to room temperature, the crude reaction mixture was flash chromatographed on silica with a step gradient of 20% and 30% EtOAc/hexanes as eluents. After concentration by rotary evaporation, 0.70 g (49% yield) of viscous yellow oil was isolated as product 4. (M + H)+ = 300.2. 1H-NMR (CDCI3) delta 7.92 (m, 1 H), 7.73 (m, 1 H), 7.60 (s, 1 H), 7.51 (d, J = 8.1 Hz, 1 H), 7.39 (m, 1 H), 7.18 (d, J= 7.8 Hz, 1 H), 6.48 (s, 1 H), 1.46 (s, 9H), 1.28 (m, 4H).

The synthetic route of 597563-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2007/47306; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1129-26-6, name is 4-Methoxybenzenesulfonamide, 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 1129-26-6, Application In Synthesis of 4-Methoxybenzenesulfonamide

To p-methoxybenzenesulfonamide (5.00 g, 26.7 mmol, 1.00 equiv) in methanol (100 mL) at 23 C was added potassium hydroxide (3.75 g, 66.8 mmol, 2.50 equiv). The reaction mixture was stirred at 23 C for 10 min and subsequently cooled to 0 C. To the reaction mixture at 0 C was added iodobenzene diacetate (8.60 g, 26.7 mmol, 1.00 equiv). The reaction mixture was stirred at 0 C for 10 min and further stirred at 23 C for 2.0 h. The reaction mixture was poured into cold water (700 mL) and kept at 0 C for 4 h. The suspension was filtered off and the filter cake was washed with water (2 x 200 mL) and methanol (2 x 200 mL) to afford 7.90 g of the title compound as a colorless solid (76% yield).NMR Spectroscopy: NMR (500 MHz, DMSO-cfe, 23 C, delta): 7.70 (d, J = 7.5 Hz, 2H), 7.49-7.44 (m, 3H), 7.32-7.28 (m, 2H), 6.78 (d, J = 8.5 Hz, 2H), 3.74 (s, 3H). 13C NMR (125 MHz, DMSO- , 23 C, delta): 160.6, 136.9, 133.2, 130.5, 130.2, 128.0, 117.0, 113.4, 55.4. These spectroscopic data correspond to the reported data in reference8.

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, 4-Methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; LEE, Eunsung; KAMLET, Adam, Seth; POWERS, David; FURUYA, Takeru; WO2012/24604; (2012); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics