Amides-buliding-blocks

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. 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., name: 6-Amino-2H-1,4-benzoxazin-3(4H)-one

A solution of 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 6.49 g, 39.5 mmol) and (2R)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (first eluting compound in step 18.i, 8.0 g, 39.5 mmol) in 9-1 EtOH/H2O (240 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure. Residual starting aniline could be removed by addition of Et2O/MeOH followed by filtration. The filtrate containing the product was concentrated under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4) to afford the title intermediate as a brown oil (5.82 g, 40percent yield).MS (ESI, m/z): 367.3 [M+H+].

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.; US2011/195949; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 147356-78-3, These common heterocyclic compound, 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, 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.

Isopropylmagnesium chloride (2.0 M in THF, 2.4 mL, 4.76 mmol) was added dropwise to a solution of a 2:1 mixture of (5S,7R)-2-bromo-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazol-7-ol and (5S,7R)-2-bromo-7-fluoro-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazole (0.470 g) and N- methoxy-N-methylcyclopropanecarboxamide (0.634 g, 4.76 mmol) in THF (15.9 mL) at 0C over 15 min. After lh, saturated aqueous ammonium chloride was added. The aqueous layer was extracted with isopropyl acetate (2 x 20 mL). The combined organic layers were dried over sodium sulfate, concentrated and the crude residue was purified by prep HPLC/SFC to afford arbitrarily assigned cyclopropyl((5S,7R)-7-fluoro-5-(o olyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l ,2,4]triazol-2-yl)methanone (137 mg, 0.480 mmol) and cyclopropyl((5S,7R)-7-hydroxy-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazol-2-yl)methanone (33.8 mg, 0.119 mmol). cyclopropyl((5S,7R)-7-fluoro-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l ,2,4]triazol-2- yl)methanone: NMR (400 MHz, DMSO-i) delta 7.33 – 7.14 (m, 3H), 6.89 (d, J= 7.5 Hz, 1H), 6.35 (ddd, J = 56.2, 6.8, 1.6 Hz, 1H), 6.19 (td, J = 6.9, 3.2 Hz, 1H), 3.59 – 3.27 (m, 1H), 3.11 – 2.91 (m, 2H), 2.38 (s, 3H), 1.14 – 1.01 (m, 4H). LCMS RT = 4.81 min, m/z = 286.1 [M + H]+. Prep SFC Information: Column: Torus Diol 5 muiotaeta, (150 x 30 mm), Mobile Phase: Carbon Dioxide (A) / 0.1 % Ammonium Hydroxide in Methanol (B), Elution Program Isocratic: 5% B Flow Rate: 150 mL/min, Column Temperature: 25 C, Wavelength: 220 nm cyclopropyl((5S,7R)-7-hydroxy-5-(o-tolyl)-6,7-dihydro-5H-pyrrolo[l,2-b][l,2,4]triazol-2- yl)methanone: NMR (400 MHz, DMSO-d6) delta 7.30 – 7.13 (m, 3H), 7.01 – 6.94 (m, 1H), 6.25 (bs, 1H), 5.75 (dd, J = 8.1, 5.8 Hz, 1H), 5.23 (dd, J = 7.9, 4.6 Hz, 1H), 3.63 – 3.52 (m, 1H), 3.03 – 2.92 (m, 1H), 2.38 (s, 3H), 2.31 – 2.14 (m, 1H), 1.09 – 0.96 (m, 4H). LCMS RT = 4.08 min, m/z = 284.1 [M + H]+. Prep HPLC Information: Column: Gemini-NX CI 8, 5muiotaeta (50 x 30 mm), Mobile Phase: 0.1 % Ammonium Hydroxide in Water (A) / Acetonitrile (B), Elution Program Gradient: 10% to 60%> B Flow Rate: 60 mL/min, Column Temperature: 25 C, Wavelength: 254 nm

The synthetic route of 147356-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); 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. 6228-73-5, name is Cyclopropanecarboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H7NO

General procedure: Synthesis of 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4) Procedure A: A mixture of 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine (3, 0.10 g, 0.37 mmol), 5-bromo-2-methylisoindolin-1-one (2, 0.10 g, 0.45 mmol), sodium tert-butoxide (54 mg, 0.56 mmol) and XPhos (5 mg, 0.01 mmol) in toluene (10 mL) was degassed with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol) was added under argon atmosphere and the reaction mixture was heated at 100 C. for 12 h. After completion of the reaction, the reaction mixture was filtered through celite pad and the filtrate was concentrated. The crude residue was purified by silica gel column chromatography using 0-10% ethyl acetate in hexanes as eluent to afford 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4). Yield: 0.11 g, 71%; MS (ESI) m/z 411 [M+1]+.

The synthetic route of 6228-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1882-71-9, name is 2-Amino-5-methoxybenzamide, molecular formula is C8H10N2O2, 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: 1882-71-9

General procedure: 2-aminobenzamide (1, 1.0 mmol), 1,3-diketone (2, 1.5 mmol), Yb(OTf)3 (0.050 mmol, 5.0 molpercent),and mesitylene (2.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 60°C (bath temp.) for 24 h with stirring. The reaction mixture was then cooled to room temperature and analyzed by GLCand GC-MS. The product 3 was isolated by medium-pressure column chromatography on silica gel(eluent: EtOAc/hexane = 30/70 ~ EtOAc 100percent. For 3j, eluent: MeOH/CHCl3 = 30/70 ~ 50/50) andrecrystallization from MeOH/hexane. The products 3l and 3m were isolated by recrystallizationfrom EtOAc/hexane. 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6 (For 3j, in a mixture of DMSO-d6 and methanol-d4). Elemental analyses were performed at the Microanalytical Center of Kyoto University. The analytical and spectral data of 3a,10 3b-c,11 3d,12 3e,13 3f,14 3g-h,10 and 3j-l,7 are fully consistent with those reported previously. The products 3i,15 and 3m16 were characterized below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1882-71-9, its application will become more common.

Reference:
Article; Yoshimura, Tsutomu; Naito, Shun-Ichi; Yuanjun, Di; Son, Aoi; Kimura, Yu; Toshimitsu, Akio; Kondo, Teruyuki; Heterocycles; vol. 93; 2; (2016); p. 816 – 823;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

To a solution of 9-cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine (prepared as described in WO 2009/085185) (152 mg, 0.6 mmol) in dioxane (6 mL) were added tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (177 mg, 0.66 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.030 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52 mg, 0.090 mmol), and sodium t-butoxide (86 mg, 0.9 mmol). The reaction mixture thus obtained was heated at 150 C. under microwave irradiation for 1 hour. The reaction mixture was diluted with DCM, washed with brine, and then dried. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 10% to 50% solvent A (DCM/MeOH/NH4OH, 100:10:1) in DCM to give the title compound as a light yellow solid (211 mg, 72% yield). 1H NMR (500 MHz, CDCl3) delta 1.52 (9H, s), 1.88-1.90 (2H, m), 2.14-2.21 (4H, m), 2.45-2.47 (2H, m), 2.92-2.94 (2H, m), 3.76-3.79 (2H, m), 4.59 (2H, m), 5.37 (1H, m), 7.49 (1H, d, J=10.0 Hz), 7.85 (1H, d, J=5.0 Hz), 8.14 (1H, br. s), 8.37 (1H, d, J=10.0 Hz), 8.52 (1H, d, J=5.0 Hz), 8.92 (1H, s), 9.11 (1H, s) ppm; LCMS m/z: 486 (M+1).

According to the analysis of related databases, 1151665-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2012/244110; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 4815-28-5, The chemical industry reduces the impact on the environment during synthesis 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-amino-4, 5, 6, 7-tetrahydrobenzo[b]thiophene-3-carboxamide 1b (1.0 mmol), ketones 2 (1.0 mmol) and InCl3 (10%, w/w) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table. After completion of the reaction (indicated by TLC) the reaction mixture was filtered to remove the insoluble catalyst and wash with acetonitrile (2 X 5mL). The filtrate was collected and concentrated under vacuum. The solid isolated was triturated in MTBE (10 mL), filtered and dried to give the desired product.

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-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ismail; Kuthati, Bhaskar; Thalari, Gangadhar; Bommarapu, Venkatesham; Mulakayala, Chaitanya; Chitta, Suresh Kumar; Mulakayala, Naveen; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1446 – 1450;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 198967-24-7, name is 2-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H10FNO2

Example 48: 4-tert-Butyl-N-[5-chloro-2-(2-fluoro-benzoyi)-pyridin-3-yl]- benzenesulfonamide; [00439] N-(2-Bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl- benzenesulfonamide (140 mg, 300 mmol) was placed in a dry 2-neck 10 mL round-bottom flask. The flask was evacuated and purged with nitrogen, followed by the addition of THF (1 mL). The homogeneous mixture was lowered to -5 C and /PrMgCI (0.33 mL, 2.0 M) was added dropwise. Upon completion of the addition, the reaction was stirred 90 minutes, followed by the slow addition of 2- fluoro-N-methoxy-N-methyl-benzamide (140 mg, 750 mmol). The reaction was stirred overnight, during which the ice-bath warmed to room temperature. The following day, the reaction was quenched with a small quantity of MeOH and the solvents evaporated in vacuo. The residue was subsequently treated with 4.0 M HCI (in dioxane) (1 mL, 4.0 mmol) and H2O (0.33 mL), and then stirred at 80 C for two hours. The resultant solution was diluted with EtOAc, washed with water, saturated sodium bicarbonate, and brine; dried with MgSO4, and evaporated employing reduced pressure. The crude sulfonamide was finally purified via preparatory TLC (20% EtOAc/hexanes) and recrystallization from MeCN/H2O to afford 98 mg of the title compound: 1H NMR (400 MHz, CDCI3) delta 10.6 (s, 1 H), 8.3 (d, 1H), 8.2 (d, 1H), 7.74 (d, 2H), 7.6 (d, 1 H), 7.5 (d, 1 H), 7.43 (d, 2H), 7.42-7.37 (m, 2H), 1.26 (s, 9H); MS (ES) M+H expect 447.1 , found 447.5.

According to the analysis of related databases, 198967-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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. 16066-84-5, name is tert-Butyl methylcarbamate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl methylcarbamate

A solution of aniline (0.911 mL, 10.0 mmol) and di-tert-butyl dicarbonate (2.34 mL, 10.2 mmol) in THF(5.0 mL) was stirred for 1 h at room temperature. The resulting mixture was concentrated to obtain N-tert-butoxycarbonylaniline(10) (2.03 g, quant.) as colorless crystals. The crude product was used without purification. (Step 2) A solution of 10 (545 mg, 2.82 mmol) and (Z)-1-bromo-4-methoxybut-2-ene (11) (422 mg,2.56 mmol) in DMF (8.5 mL) was treated with sodium hydride (60 wt.% in oil, 154 mg, 3.85 mmol) at 0 C. The resulting mixture was stirred for 1 h at 50 C and quenched with saturated aqueous ammonium chloride at 0 C.Extractive workup and purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 5/1 asthe eluent) afforded (Z)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate (12) (654 mg, 92% yield) as acolorless oil. (Step 3) A solution of diisopropylamine (484 L, 3.45 mmol) in THF (4.2 mL) was treated with a1.6 M n-butyllithium hexane solution (2.30 mL, 3.7 mmol) at 0 C under an argon atmosphere and the mixture was stirred for 30 min at the same temperature. A solution of 12 (649 mg, 2.34 mmol) in THF (7.5 mL) was added to the solution at 0 C and the mixture was stirred for 3 h at the same temperature. The resulting mixturewas quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified bychromatography on silica gel (hexane/ethyl acetate = 20/1 as the eluent) to give 2f (516 mg, 90% yield)

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; Tayama, Eiji; Horikawa, Kouki; Iwamoto, Hajime; Hasegawa, Eietsu; Tetrahedron Letters; vol. 55; 19; (2014); p. 3041 – 3044;,
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. 317595-54-3, name is tert-Butyl (2-aminocyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 317595-54-3

The resulting triethylammonium chloride was removed by filtration and to the filtrate was added N-(t-butoxycarbonyl)-trans 1,2-diaminocyclohexane.

The synthetic route of 317595-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Associated Universities, Inc.; US5089663; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 148017-28-1, name is tert-Butyl sulfamoylcarbamate, 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 148017-28-1, Safety of tert-Butyl sulfamoylcarbamate

Example 65; N-[((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl]sulfamide (Compound I-56); Step a: tert-butyl(aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate; ((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (700.0 mg, 0.001462 mol), N-Boc-sulfonamide (398 mg, 0.00203 mol) and triphenylphosphine (575 mg, 0.00219 mol) were dissolved in ethyl acetate (28 mL, 0.28 mol) at 50 C. under an atmosphere of nitrogen. Diethyl azodicarboxylate (350.0 muL, 0.002223 mol) was added over 2-3min and the mixture was stirred at 50 C. for 30 minutes. The cooled mixture was evaporated and the residue purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product as a white solid, 636 mg (66%). LC/MS: Rt=2.55 min, ES+ 657 (AA standard).

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; Millennium Pharmaceuticals, Inc.; US2007/191293; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics