Tag: M.W=100-200

Synthetic Route of 16375-88-5,Some common heterocyclic compound, 16375-88-5, name is N-(4-(Hydroxymethyl)phenyl)acetamide, molecular formula is C9H11NO2, 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: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard.

The synthetic route of 16375-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Unsworth, Christopher A.; Coulson, Ben; Chechik, Victor; Douthwaite, Richard E.; Journal of Catalysis; vol. 354; (2017); p. 152 – 159;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 4424-80-0,Some common heterocyclic compound, 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, molecular formula is C10H11NO, 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.

Step 1 Production of 2,3,4,5-tetrahydro-1H-benzo[b]azepine Lithium aluminum hydride (100 mg) was suspended in tetrahydrofuran (10 mL), 1,3,4,5-tetrahydrobenzo[b]azepin-2-one (245 mg) was added under ice-cooling by small portions. After heating under reflux for 5.5 hrs, water (0.1 mL), 15% aqueous sodium hydroxide (0.1 mL) and water (0.3 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate, and concentrated to give the title compound (301.6 mg) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; US2008/64871; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 198211-38-0, name is tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate, 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. Safety of tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate

General procedure: Intermediate C17.ii (130 mg) and K2C03 (69 mg) were suspended with DMF. 6-(Boc-amino)-3-azabicyclo[3. 1.0]hexane (81 mg; commercial) was added portionwise and themixture was stirred at rt for 1 day. The mixture was concentrated under reduced pressure and the residue was portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with water and brine, dried over Mg504 and concentrated under reduced pressure. The title compound was obtained, after purificationby CC (Combiflash; Hept/EA 0:1 to 1:0), as a yellow oil (108 mg; 62% yield). M53 (ESI, mlz): 457.10 [M+H+]; tR = 0.73 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 198211-38-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; RUEEDI, Georg; ZUMBRUNN, Cornelia; (200 pag.)WO2016/59097; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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

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

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

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

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

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

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