Research on new synthetic routes about 88-19-7

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 of 88-19-7, A common heterocyclic compound, 88-19-7, name is 2-Methylbenzenesulfonamide, molecular formula is C7H9NO2S, 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.

3-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-1H-indol-5-yl)carbamic acid cyclopentyl ester: Under a nitrogen atmosphere, a mixture of 4-(5-cyclolpentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid (800 mg, 1.9 mmol), toluene-2-sulfonamide (341 mg, 2 mmol), 4-(dimethylamino)pyridine (244 mg, 2 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (384 mg, 2 mmol) was dissolved in dichloromethane (30 mL). The mixture was stirred at ambient temperature for about 18 hours, and then poured into 1 M hydrochloric acid (100 mL). Following standard extractive workup with chloroform, the crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=2/1, v/v, elution) to afford the title compound (200 mg, 18%). 1H NMR (300 MHz, CDCl3) delta 8.62 (s, 1H), 8.29 (d, 1H, J=8.1 Hz), 7.55-7.22 (m, 9H), 6.81 (s, 1H), 6.50 (s, 1H), 5.23 (s, 1H), 4.08 (s, 2H), 3.91 (s, 3H), 3.75 (s, 3H), 2.71 (s, 3H), 1.96-1.76 (m, 8H); LC-MS: m/z=576 (MH)+; HPLC: 99% (Purity).

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; AUSPEX PHARMACEUTICALS, INC.; US2009/191183; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Simple exploration of 20188-40-3

The chemical industry reduces the impact on the environment during synthesis 4-(Aminomethyl)benzamide hydrochloride. I believe this compound will play a more active role in future production and life.

Reference of 20188-40-3, 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. 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Example A85 Preparation of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(4- carbamoylbenzyl)amino]-2-oxoethyl}-4-hydroxy-l,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4- dien-l-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate (B266). Step 1. Synthesis of (2S,32)-5- {[(2R,3R,5S,6S)-6- {(2¡ê’,4¡ê’)-5-[(3R,4R,5R,7S)-7-{2-[(4- carbamoylbenzyl)amino]-2-oxoethyl}-4-hydroxy-l,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien- l-yl} -2,5-dimethyltetrahydro-2H-pyran-3-yl]amino} -5-oxopent-3-en-2-yl acetate (B266). To a solution of B1 (18.7 mg, 0.03 mmol, 1 eq.) in NN-dimethylformamide (0.5 mL) at rt was added NN- diisopropylethylamine (21.2 L, 0.12 mmol, 2 eq.) and 4-(aminomethyl)benzamide hydrochloride salt (11.2 mg, 0.06 mmol, 2 eq.), and the reaction was stirred for 1 h. The reaction was purified by by reverse phase chromatography (Method A) to give B266 as a white solid. Yield: 15.4 mg, 0.023 mmol, 77percent. LCMS (Protocol D): m/z 668.37 [M+Na]+, retention time = 0.71 minutes. lB NMR (500 MHz, DMSO-d6) delta 8.50-8.43 (m, 1 H), 7.88 (s, 1 H), 7.82-7.74 (m, 3 H), 7.33-7.25 (m, 3 H), 6.41-6.27 (m, 2 H), 6.10 (d, J= 11.6 Hz, 1 H), 5.87 (dd, J= 11.6 and 7.5 Hz, 1 H), 5.62 (dd, J= 15.8 and 5.5 Hz, 1 H), 5.50-5.43 (m, 1 H), 5.04 (d, J= 5.4 Hz, 1 H), 4.43-4.20 (m, 3 H), 3.68-3.59 (m, 2 H), 3.53-3.45 (m, 1 H), 3.29-3.23 (m, 1 H), 2.78 (d, J= 5.3 Hz, 1 H), 2.68-2.56 (m, 2 H), 2.35-2.13 (m, 3 H), 1.98 (s, 3 H), 1.90-1.72 (m, 4 H), 1.70 (s, 3 H), 1.66-1.58 (m, 1 H), 1.57-1.49 (m, 1 H), 1.25 (d, J= 6.5 Hz, 3 H), 1.04 (d, J= 6.2 Hz, 3 H) , 0.93 (d, J= 7.3 Hz, 3 H).

The chemical industry reduces the impact on the environment during synthesis 4-(Aminomethyl)benzamide hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; DIRICO, Kenneth John; EUSTAQUIO, Alessandra S.; GREEN, Michael Eric; HE, Haiyin; HE, Min; KOEHN, Frank Erich; O’DONNELL, Christopher John; PUTHENVEETIL, Sujiet; RATNAYAKE, Anokha Sayani; SUBRAMANYAM, Chakrapani; TESKE, Jesse Alexander; YANG, Hui Yu; WO2014/68443; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

New downstream synthetic route of 2895-21-8

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-Isopropyl-2-chloroacetamide, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 2895-21-8, name is N-Isopropyl-2-chloroacetamide, 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 2895-21-8, Recommanded Product: 2895-21-8

To a solution of 3-(3-(3-chloro-4-fluorophenyl)-1-oxo-1 ,2-dihydropyrrolo[1 ,2-a]pyrazin-7- yloxy)propyl acetate (160 mg, P102) in CH3CN (10 ml_) K2CO3 (88 mg) and 2-chloro-N- isopropylacetamide (69 mg) were added and the mixture was heated to reflux for 16h, then cooled to RT and filtered. The filtrate was concentrated in vacuo, the crude was dissolved in THF (10 ml_) and a 2M solution of LiOH in water (1 ml_) was added. The mixture was stirred at RT for 16h, and then extracted with EA (20 ml_ X 5). The organic layer was dried, evaporated and the residue was combined with one other batch to give 260 mg of the crude product. The crude was purified by preparative HPLC to give the title compound (15 mg).1H NMR (400 MHz, CD3OD) delta: 1.03-1.06 (6H, d), 1.83-1. 91 (2H, m), 3 .57-3. 67 (2H, t),3. .75-3. .85 (1 H, m), 3.96-3.99 (2H, t), 4.29 (2H, s), 6. 59 (1 H , s), 6.96 91 H, s), 7. 09 (1 H, s),7. .20-7. .28 (1 H, t), 7 .30-7.37 (1 H, m), 7.50(1 H, m).

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-Isopropyl-2-chloroacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/130231; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Simple exploration of 75178-90-4

According to the analysis of related databases, 75178-90-4, the application of this compound in the production field has become more and more popular.

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. 75178-90-4, name is tert-Butyl (5-hydroxypentyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H21NO3

General procedure: To a stirred solution of tert-butyl 5-hydroxypentyl-carbamate(500 mg, 2.46 mmol) and TEA (498 mg, 4.92 mmol) in 5mL DCMat -10 C was added MsCl (338 mg, 2.95 mmol) dropwise and thesolution was stirred at the same temperature for 5 h. The reactionwas then quenched with water. The organic layer was washed withwater, brine, dried over MgSO4, filtered and evaporated underreduced pressure to give the desired product as yellow oil (552 mg,80%, Rf 0.5 (EtOAc)) The mesylatewas used in the next step withoutany further purification. Under N2 atmosphere 5-(tert-butoxycarbonylamino)pentyl methanesulfonate (350 mg, 1.2 mmol) wasdissolved in 5mL THF followed by the addition of LiBr (313 mg,3.6 mmol) to the solution. The reaction mixture was stirred for 16 hunder reflux, then THF was removed under vacuum. The mixturewas diluted with 10 mL water and it was extracted with DCM(3 x 10 mL). The combined organic phase was washed with water(3 x 10 mL) and brine (3 x 10 mL), dried over MgSO4 and evaporatedin vacuo. The product was purified by column chromatographyon silica gel 60 (n-hexane-EtOAc 9:1) to give whitecrystalline product (230 mg, 72%).

According to the analysis of related databases, 75178-90-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dvoracsko, Szabolcs; Keresztes, Attila; Mollica, Adriano; Stefanucci, Azzurra; Macedonio, Giorgia; Pieretti, Stefano; Zador, Ferenc; Walter, Fruzsina R.; Deli, Maria A.; Kekesi, Gabriella; Banki, Laszlo; Tuboly, Gabor; Horvath, Gyoengyi; Toemboely, Csaba; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 571 – 588;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 16982-21-1

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-amino-2-thioxoacetate. I believe this compound will play a more active role in future production and life.

Related Products of 16982-21-1, 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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, This compound has unique chemical properties. The synthetic route is as follows.

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of amino-thioxo-acetic acid ethyl ester (2.50 g, 18.77 mmol) and 1 ,3-dichloro-propan-2-one (2.88 g, 21.59 mmol) in toluene (20.0 ml.) was stirred for 2 h at reflux. EtOAc (20 ml.) was added at rt and the mixture was washed with sat. aq. NaHCO3 (10 ml.) followed by brine (20 ml_). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a light yellow oil. TLC: rf (4:1 hept-EA) = 0.26. LC-MS-conditions 02: tR = 0.89 min, [M+H]+ = 206.40.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-amino-2-thioxoacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/77990; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The origin of a common compound about 711007-44-2

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.

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, Product Details of 711007-44-2

Example 3: Benzyl 2-(4-carbamoyl-lH-benzo[d]imidazol-2-yl) indoline-1-carboxylate[00150] Step-1: To a solution of l-((benzyloxy)carbonyl)indoline-2-carboxylic acid (1.0 g, 3.37 mmol) in anhydrous DMF (20 ml) was added EDCHCl (1.93 g, 10.10 mmol), HOBt (681 mg, 5.05 mmol) and triethylamine (0.7 ml, 5.05 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (635 mg, 4.20 mmol) was added and heated to 8O0C over night. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum to yield benzyl 2-(2-amino- 3-carbamoylphenylcarbamoyl) indoline-1-carboxylate. MS (ES+): m/z 431.1 [M+H]+

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; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; LIM, Dong, Sung; SMITH, David, E.; WO2011/2520; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Brief introduction of 127828-22-2

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.

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)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 127828-22-2, SDS of cas: 127828-22-2

To a stirred solution of 5g of 2-{(3-butynyl)-l-oxy}ethyl methanesulfonate and 5.32g of 2-[2-{2-(t-butoxycarbonyl)amino}ethyl-l- oxy]ethylamine in 60ml acetonitrile, was added drop-wise 3.6g of potassium carbonate dissolved in water at O0C. The reaction solution was allowed to slowly warm to RT and stirred for another 24h, and then concentrated under reduced pressure. The resulting residue was dissolved in MC and washed with water. The organic layer was concentrated and dissolved in 80ml THF and 80ml water, to which was added 8.4g of BoC2O dissolved in 50ml THF. The reaction mixture was stirred at RT for 16h, which was followed by removal of THF in vacuo and extraction with EA. The organic layer was washed in series with 0.5M aq citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (hexane -> 1:4 EA/hexane) to obtain 2.45g of compd 9 as a pale yellow oil. 1H NMR (400MHz; CDCI3) delta 5.08 (br s, 0.5H), 4.93 (br s, 0.5H), 3.61-3.46 (m, 12H), 3.31 (m, 2H), 2.48 (m, 2H), 1.99 (t, IH), 1.48 (s, 9H), 1.46 (s, 9H).

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; CTI BIO; WO2009/113828; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of 198989-07-0

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.

Adding a certain compound to certain chemical reactions, such as: 198989-07-0, name is tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, 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 198989-07-0, COA of Formula: C10H18N2O2

[00170] Methanesulfonic anhydride (Ms2O) (662 mg, 3.81 mmol) was slowly added to a solution of 5-formyl-1-(2-hydroxyethyl)-4-methyl-1H-indole-2-carbonitrile (290 mg, 1.27 mmol) and DIPEA (1.1 mL) in THF (6.3 mL). After stirring for 10 minutes, the mixture was diluted with saturated bicarbonate solution and stirred for 20 minutes, and the product was filtered off and thoroughly dried.1H NMR (600 MHz, CD3CN): 10.39 (s, 1H), 7.88 (d, 1H, J=8.4Hz), 7.59 (s, 1H), 7,49 (d, 1H, J=8.4Hz), 4.66 (m, 2H), 4.53 (m, 2H), 2.86 (m, 6H). The mesylated derivative (130 mg, 0.42 mmol) was dissolved in DMF (2 mL) and tert-butyl 2,5- diazabicyclo[2.2.1]heptane-2-carboxylate (166 mg, 0.84 mmol) and potassium carbonate (86 mg, 0.63 mmol) were added. The mixture was heated at 85 C for 1 h, cooled down, diluted with water, and extracted with DCM. The crude fied on silica gel column to produce tert-butyl 5-(2-(2-cyano-5-formyl-4-methyl-1H-indol-1-yl)ethyl)-2,5-diazabicyclo[2.2.1]heptane- 2-carboxylate (10 mg). HR MS (ESI): C23H28N4O3 + H+ calculated 409.2234; found 409.2232.

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; KURA ONCOLOGY, INC.; WU, Tao; LI, Liansheng; WANG, Yi; REN, Pingda; LIU, Yi; SNYDER, Ryan Kent; (342 pag.)WO2018/106818; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A new synthetic route of 621-38-5

According to the analysis of related databases, 621-38-5, the application of this compound in the production field has become more and more popular.

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. 621-38-5, name is 3-Bromoacetanilide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromoacetanilide

0.05 g of tetrakistriphenylphosphine palladium was added at room temperature to a solution having 0.21 g of 3-bromo-acetoanilide obtained by (1) dissolved in 5 ml of toluene, followed by stirring for 15 minutes. 0.25 g of 2,4, 6-trimethylphenyl boronic acid,. 2 ml of ethanol and 3 ml of a 2M sodium carbonate solution were sequentially added thereto, and the reaction system was flushed with nitrogen, followed by stirring for 12 hours under reflux under heating. After cooling, 10 ml of cold water was added, followed by extraction with 15 ml and 10 ml of ethyl acetate. The organic layers were put together and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel (Silica gel 60N; spherical and neutral, manufactured by Kanto Kagaku) column chromatography (developing solvent of n-hexane: ethyl acetate=2: 1) to obtain 0.15 g of the objective compound having a melting point of 173. 8C. Further, NMR of this compound was as follows. H-NMR 5 (ppm) 1. 98 (s, 6H), 2.15 (s, 3H), 2. 30 (s, 3H), 6. 85 (d, lH ; J =8. 0 Hz), 6. 90 (s, 2H), 7.16 (s, lH), 7. 33 (t, lH; J =8. 0 Hz), 7.41 (bs, lH), 7.57 (d, lH; J =8.0 Hz)

According to the analysis of related databases, 621-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.?; WO2005/44007; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Share a compound : 113778-69-1

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

Synthetic Route of 113778-69-1,Some common heterocyclic compound, 113778-69-1, name is N-Methoxy-N-methylisobutyramide, molecular formula is C6H13NO2, 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 N’-(4-bromo-5-methoxy-2-methyl-phenyl)-N-ethyl-N-methyl-formamidine (2.0 g, 7.01 mmol) in dry tetrahydrofuran (3.5 mL) under IS -atmosphere was added drop wise to a suspension of LiCI (0.33 g, 7.71 mmol) and Mg-turnings (0.26 g, 7.02 mmol) in dry tetrahydrofuran (3.5 mL) at a temperature between 20 C to 40 C (temperature controlled by addition rate). Upon completed addition, the reaction was aged for 1 h at 40 C and then the mixture was then cooled to 0 C. N-methoxy-N,2-dimethyl-propanamide (1.01 g, 7.33 mmol) was added drop wise and the reaction was mixture was gradually warmed to RT over 1 h. Aqueous NH4CI solution was added and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSC>4, filtrated and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford the title compound as light yellow oil . 1H NMR (400 MHz, CDC) delta 7.47 (br. s, 2H), 6.30 (s, 1H), 3.85 (s, 3H), 3.25 – 3.60 (m, 3H), 3.02 (s, 3H), 2.18 (s, 3H), 1.59 (s, 1H), 1.23 (t, 3H), 1.13 (d, 6H).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WEISS, Matthias; GAGNEPAIN, Julien, Daniel, Henri; HOFFMAN, Thomas, James; SULZER-MOSSE, Sarah; LAMBERTH, Clemens; (86 pag.)WO2017/102635; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics