November 2020 - Page 14 of 21 - Heterocyclic Building Blocks-Pyrrolines

Little discovery in the laboratory: a new route for 25021-08-3

A chemical reaction often occurs in steps, although it may not always be obvious to an observer. Thank you very much for taking the time to read this article. If you are also interested in other aspects of 25021-08-3, you can also browse my other articles.

25021-08-3, Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.25021-08-3, name is 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid, below Introduce a new synthetic route.

250 mg (1.07 mmol) of tert-Butyl 3-[2-(2-aminoethoxy)ethoxy]propanoate, 151 mg (0.974 mmol) of 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid, 224 mg (1.46 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 224 mg (1.17 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in 5.0 ml of dimethylformamide. The reaction mixture was stirred at RT for 1 h. Ethyl acetate was added and the mixture was extracted twice with 5% strength citric acid solution and with saturated sodium bicarbonate solution. The organic phase was washed twice with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was evaporated under reduced pressure. The residue was purified by preparative RP-HPLC (column: Reprosil 250*40; 10mu, flow rate: 50 ml/min, MeCN/water/0.1% TFA). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 267 mg (64% of theory) of tert-Butyl 3-[2-(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethoxy)ethoxy]propanoate. LC-MS (Method 1): Rt=0.73 min; MS (ESIpos): m/z=371 (M+H)+.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; WITTROCK, Sven; BERNDT, Sandra; GRITZAN, Uwe; FITTING, Jenny; STELTE-LUDWIG, Beatrix; JONES, Patrick; MAHLERT, Christoph; VOTSMEIER, Christian; SCHOeNFELD, Dorian; TRAUTWEIN, Mark; WEBER, Ernst; PAWLOWSKI, Nikolaus; GREVEN, Simone; GLUeCK, Julian Marius; HAMMER, Stefanie; DIETZ, Lisa; MAeRSCH, Stephan; (357 pag.)US2020/138970; (2020); A1;,
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Little discovery in the laboratory: a new route for 69778-83-2

There are, however, a few established termolecular elementary reactions. The reaction of nitric oxide with oxygen appears to involve termolecular steps. you can also browse my other articles about 69778-83-2

69778-83-2, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular.69778-83-2, name is 4-Methoxy-1H-pyrrol-2(5H)-one. A new synthetic method of this compound is introduced below.

To a solution of phosphoryl bromide (220 molpercent, 5.58 g) in dry dichloromethane (20 mL) was added DMF (220 molpercent, 1.4 mL) dropwise over 2 minutes. The resulting reaction mixture was stirred at room temperature for 30 min and concentrated in vacuo to provide the Vilsmeyer complex as a white solid. After drying in vacuo for Ih, the white solid was suspended in dry dichloromethane (20 mL) and cooled to 0 0C. A solution of 4-methoxy-3- pyrrolin-2-one (A) (Ig, 8.84 mmol) in dichloromethane (10 mL) was added dropwise and the102USlDOCS 550694W1 EPO resulting reaction mixture was stirred at 0 0C for 30 min, then at room temperature for 20 h. The mixture was poured onto ice (75 mL), treated with aqueous NaOH 4N (50 mL), diluted with EtOAc (100 mL), and stirred for 15 min. The layers were separated, and the aqueous layer was extracted with EtOAc (3 x 60 mL). The combined organic layers were washed with brine (3 x 200 mL,), dried over Na2SO4, filtered and concentrated in vacuo to afford a crude residue that was purified using flash column chromatography over silica gel with a gradient elution of 0-20percent EtOAC/Hexanes to provide Compound B as a white solid. NMR 1H (300 MHz, CDCl3): delta (ppm) 3.95 (s, 3H); 5.90 (s, IH); 9.30 (s, IH), 9.92-10.34 (bs, IH). m/z: 205.1 [M+ 1]

Reference£º
Patent; GEMIN X BIOTECHNOLOGIES INC.; WO2006/89397; (2006); A1;,
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The effect of the change of Quinine synthetic route on the product

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The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular.1122-10-7, name is 3,4-Dibromo-1H-pyrrole-2,5-dione. A new synthetic method of this compound is introduced below., 1122-10-7

General procedure: To a stirred solution of 2,3-dibromomaleimide23 (1.0 mmol) in CH2Cl2 (20ml) Et3N (2.0mmol) and thiol (2.1mmol) were added under argon atmosphere and stirred for 3 h at room temperature. The reaction mixture was evaporated,and the crude product was purified by flash chromatography to give the desired compound.

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Reference£º
Article; Csavas, Magdolna; Miskovics, Adrienn; Szcs, Zsolt; Rth, Erzsebet; Nagy, Zsolt L; Bereczki, Ilona; Herczeg, Mihaly; Batta, Gyula; Nemes-Nikodem, Eva; Ostorhazi, Eszter; Rozgonyi, Ferenc; Borbas, Aniko; Herczegh, Pal; Journal of Antibiotics; vol. 68; 9; (2015); p. 579 – 585;,
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Little discovery in the laboratory: a new route for 25021-08-3

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid. We look forward to the emergence of more reaction modes in the future.

25021-08-3, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular.25021-08-3, name is 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid. A new synthetic method of this compound is introduced below.

1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-oxo-6,9,12,15,18,21,24,27-octaoxa-3-azatriacontan-30-oic acid Tert-Butyl 1-amino-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-oate (100 mg, 201 mumol) was initially charged in 1.0 ml of DMF and (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid (46.8 mg, 301 mumol), 1-hydroxy-1H-benzotriazole hydrate (76.9 mg, 502 mumol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (77.0 mg, 402 mumol) were added. The reaction mixture was stirred overnight at RT and then ethyl acetate was added. The organic phase was washed twice with 5% citric acid solution, with sat. sodium hydrogen carbonate solution and then with sat. sodium chloride solution. The organic phase was dried over magnesium sulfate. The solvents were evaporated under vacuum and the residue purified by prep. RP-HPLC (column: Reprosil 125*30; 10mu, flow: 50 mL/min, MeCN/water/0.1% TFA). The solvents were evaporated under vacuum and the residue dried under high vacuum. This gave 19.1 mg (13% of theory) of the compound tert-Butyl 1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-oxo-6,9,12,15,18,21,24,27-octaoxa-3-azatriacontan-30-oate. LC-MS (Method 1): Rt=0.87 min; MS (ESIpos): m/z=635 [M+H]+, 25021-08-3

Fun Route: New Discovery of N-(2-Aminoethyl)maleimide Hydrochloride

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A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.134272-64-3, name is N-(2-Aminoethyl)maleimide Hydrochloride. An updated downstream synthesis route of 134272-64-3 as follows., 134272-64-3

(DM 1 -GMB- Ala-Gly-Gly)2-Lys-b-Ala-OH (5.3 mg, 0.0022 mmol) was dissolved in anhydrous dimethylformamide (0.25 mL) to which was added EDC (2.0 mg, 0.014 mmol). After 2 min 2-amino-ethyl-maleimide HC1 salt (1 mg, 0.0057 mmol) was added and the solution was stirred at room temperature for 15 min. The reaction mixture was purified by HPLC on a XB-C18 21.2×150 mm, 5muiotaeta column with a flow rate of 21.2mL/min. eluting with deionized water containing 0.1% formic acid using a gradient of acetonitrile 5% for 4 min then a linear gradient of 5% – 95% over 17 min. Fractions containing desired product were combined, frozen and lyophilized to give 2 mg (35 % yield) of white solid. MS [M + Na]+ calcd. 2537.0; found 2537.3.

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Reference£º
Patent; IMMUNOGEN, INC.; WIDDISON, Wayne, C.; CHARI, Ravi, V.J.; WO2014/194030; (2014); A2;,
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Derivation of elementary reaction about 872-32-2

An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.872-32-2, name is 2-Methyl-1-pyrroline. Here is a downstream synthesis route of the compound 872-32-2. 872-32-2

General procedure: Keeping the temperature at about 0 ¡ãC, trifluoroacetic acid (0.95 mL, 12.5 mmol), KHF2 (585 mg, 7.5 mmol), and trifluoromethyltrimethylsilane (1.9 mL, 12.5 mmol) were successively added to a solution of the corresponding imine 1, 2 or 3 (10 mmol) in dry acetonitrile (50 mL). After stirring for 12 h at rt, the solvent was gently evaporated under reduced pressure, the residue was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ether (3.x.10 mL). The combined extract was dried over Na2SO4, the solvent was evaporated at reduced pressure and the residue was purified by column chromatography on silica gel eluting with a 20/1 mixture of hexane/ethyl acetate. This afforded the tagged amine. In the case of volatile amines 4a, 4d, 5a, 6a, 8a, and 8b the combined extract was mixed with hydrochloric acid (1.5 mL), evaporated to dryness, and the residue was washed with pentane. In this way the amines 4a, 4d, 5a, 6a were isolated as hydrochloride. For comparison to the reported data, the hydrochloride of 2-Tfm-pyrrolidine 8a and 2-Tfm-piperidine 8b were again treated with aqueous NaHCO3 and were analyzed as free bases.

Reference£º
Article; Shevchenko, Nikolay E.; Vlasov, Katja; Nenajdenko, Valentine G.; Ro?schenthaler, Gerd-Volker; Tetrahedron; vol. 67; 1; (2011); p. 69 – 74;,
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Fun Route: New Discovery of 1,10-Phenanthrolin-5-amine

55750-49-7, A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.55750-49-7, name is Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate. An updated downstream synthesis route of 55750-49-7 as follows.

55750-49-7, a) N-(tert.-butyloxycarbonyl)-2-(N-maleinimido)ethylamine 0.8 g (5 mmol) of the compound produced according to Example 1a is dissolved in 25 ml saturated sodium bicarbonate solution. The solution is filtered over a folded filter and cooled to 0 C. Subsequently 0.84 g (5 mmol) N-(ethoxycarbonyl)maleinimide (produced according to the method of O. Keller and J. Rudinger, Helv. Chim. Acta 58 (1975), 531-541) is added while stirring and it is left to stir for a further 15 min at room temperature. During this the N-(ethoxycarbonyl)maleinimide dissolves completely after a short time while the title compound precipitates during the course of the reaction. 40 ml THF is added and stirred for a further 45 min at room temperature. Afterwards it is adjusted to pH 6.0 with 1n HCl, extracted twice with 50 ml acetic ester and the extract is dried with 5 g Na2 SO4. After evaporation in a water-jet vacuum the title compound is obtained as a colourless, solid residue. Yield: 1.1 g (92% of the theoretical yield). TLC: silica gel, chloroform/acetic ester (66/33 v/v), spray with 0.1% KMnO4 solution; Rf =0.50.

Reference£º
Patent; Boehringer Mannheim GmbH; US5595741; (1997); A;,
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Little discovery in the laboratory: a new route for 1122-10-7

1122-10-7, A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.1122-10-7, name is 3,4-Dibromo-1H-pyrrole-2,5-dione. An updated downstream synthesis route of 1122-10-7 as follows.

The effect of 55750-48-6 reaction temperature change on equilibrium

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of 55750-48-6. We look forward to the emergence of more reaction modes in the future.

One of the major reasons is to use measurements of the macroscopic properties of a system, such as the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 55750-48-6, name is Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate, introduce a new downstream synthesis route., 55750-48-6

55750-48-6, Step 1 : t-Butyl (2-(2-(2-aminoethoxy)ethoxy)ethyl)carbamate(250 mg, 1 .0 mmol) and methyl 2,5-dioxo-2,5-dihydro-1 H-pyrrole-1 -carboxylate (156 mg, 1 .0 mmol) were combined in saturated aqueous NaHC03 (10 ml) and stirred for 1.5 h at 0C. The reaction mixture was acidified to pH 2 with hydrochloric acid (2 M) and extracted with EtOAc. The organic phase was washed with brine, dried with MgS04, and concentrated. The crude was purified by ISCO using 0-4% MeOH/DCM to give t-butyl (2-(2-(2-(2,5- dioxo-2,5-dihydro-1 H-pyrrol-1 -yl)ethoxy)ethoxy)ethyl)carbamate as a colorless oil. MS m/z 229.2(M+1 -Boc). Retention time 0.963 min.1H NMR (400 MHz, Chloroform-d) delta 6.71 (s, 2H), 5.04 (bs, 1 H), 3.74 (t, J = 5.4 Hz, 2H), 3.64 (t, J = 5.4 Hz, 2H), 3.61 -3.59 (m, 2H), 3.56-3.54 (m, 2H), 3.50 (t, J = 5.2 Hz, 2H), 3.31 -3.26(m, 2H), 1.44 (s, 9H).

This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of 55750-48-6. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; IRM LLC; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; JIN, Yunho; WO2015/95301; (2015); A2;,
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Flexible application of 33454-82-9 in synthetic route

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A balanced equation for a chemical reaction indicates what is reacting and what is produced, but it reveals nothing about how the reaction actually takes place. The reaction mechanism is the process, or pathway, by which a reaction occurs.872-32-2, name is 2-Methyl-1-pyrroline. An updated downstream synthesis route of 872-32-2 as follows., 872-32-2

Example 6 5-(5-(4-Fluorophenyl)-4-(pyridin-2-ylmethylamino)pyrrolo[1,2-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide The commercially available methyl 3-chloro-1H-pyrrole-2-carboxylate (1.50 g, 94.0percent, yellow solid) was synthesized according to Fang et al., J. Med. Chem., 53:7967-7978 (2010) using 2-methyl-1-pyrroline (0.831 g, 10.0 mmol, commercial), NCS (10.7 g, 80.0 mmol) and NaOMe in MeOH (3M, 20 mL, 60.0 mmol). LCMS Condition B-41: retention time 1.71 min, [M+1]=160.10. 1H NMR (400 MHz, CDCl3) delta 3.90 (s, 3H), 6.25 (t, J=3.0 Hz, 1H), 6.86 (t, J=3.0 Hz, 1H), 9.17 (br s, 1H)., 872-32-2

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Patent; Finlay, Heather; Adisechan, Ashok Kumar; Dhondi, Naveen Kumar; Govindrajulu, Kavitha; Gunaga, Prashantha; Lloyd, John; Srinivasu, Pothukanuri; US2014/256719; (2014); A1;,
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