25021-08-3| - Heterocyclic Building Blocks-Pyrrolines

Analyzing the synthesis route of 25021-08-3

25021-08-3, The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

25021-08-3, 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Trifluoroacetic Acid/(2S)-2-amino-4-[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]-N-{2-[(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethyl)sulphonyl]ethyl}butanamide (1:1) The title compound was prepared from Intermediate L81 by coupling with Intermediate C58 in the presence of HATU and N,N-diisopropylethylamine. In the next step, the Z protective group was removed by hydrogenation over 10% palladium on activated carbon in DCM/methanol 1:1 at RT under hydrogen standard pressure for 30 min. The deprotected intermediate was then converted by coupling with (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N-diisopropylethylamine and finally by deprotection with zinc chloride into the title compound. LC-MS (Method 1): Rt=0.83 min; MS (ESIpos): m/z=785 (M+H)+.

25021-08-3, The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Pharma Aktiengesellschaft; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; MARX, Leo; STELTE-LUDWIG, Beatrix; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (684 pag.)US2018/169256; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Downstream synthetic route of 25021-08-3

As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25021-08-3,2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid,as a common compound, the synthetic route is as follows.

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 at RT overnight, and ethyl acetate was then added. The organic phase was washed twice with 5% citric acid solution, with saturated sodium hydrogencarbonate solution and once with saturated sodium chloride solution. The organic phase was dried over magnesium sulphate. The solvents were evaporated under reduced pressure and the residue was purified by preparative RP-HPLC (column: Reprosil 125*30; 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 19.1 mg (13% of theory) of 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

As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

Brief introduction of 25021-08-3

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

N-[(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]-beta-alanine The title compound was prepared from commercially available (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid by coupling to tert-butyl beta-alaninate hydrochloride (1:1) in the presence of EDCI/HOBt and N,N-diisopropylethylamine and subsequent deprotection with trifluoroacetic acid. LC-MS (Method 1): Rt=0.32 min; MS (ESIpos): m/z=227 (M+H)+., 25021-08-3

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; MARX, Leo; JOHANNES, Sarah Anna Liesa; STELTE-LUDWIG, Beatrix; DIETZ, Lisa; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (481 pag.)US2019/77752; (2019); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Simple exploration of 25021-08-3

25021-08-3 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid 319935, apyrrolines compound, is more and more widely used in various.

1-[(N-({(2S)-2-Amino-4-[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]butanoyl}-3-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) acetyl]amino}-D-alanyl)amino]-3,6,9,12-tetraoxapentadecan-15-oic Acid/Trifluoroacetic Acid (1:1) First, intermediate L91 was coupled with (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N-diisopropylethylamine, and the Boc protective group was then removed using 12.5% strength TFA in DCM. The resulting intermediate was coupled with intermediate C58 in the presence of HATU and N,N-diisopropylethylamine and then converted into the title compound by deprotection with zinc chloride. LC-MS (Method 1): Rt=0.84 min; MS (ESIpos): m/z=984 (M+H)+., 25021-08-3

25021-08-3 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid 319935, apyrrolines compound, is more and more widely used in various.

Downstream synthetic route of 25021-08-3

25021-08-3, As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

Trifluoroacetic acid/N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}-2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetamide (1:1) 200 mg (0.805 mmol) of tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate, 150 mg (0.966 mmol) of (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid and 560 mul (3.2 mmol) of N,N-diisopropylethylamine were dissolved in 10 ml of dimethylformamide, and 459 mg (1.21 mmol) of HATU were added. The reaction mixture was stirred at RT for 30 minutes. The solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed twice with 5% citric acid solution and dried over magnesium sulphate, and the solvent was evaporated under reduced pressure. The residue was purified using Biotage Isolera (silica gel, column 25 g SNAP, dichloromethane:methanol 98:2). This gave 276 mg (89% of theory) of tert-butyl {2-[2-(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethoxy)ethoxy]ethyl}carbamate. LC-MS (Method 1): Rt=0.67 min; MS (ESIpos): m/z=386 (M+H)+.

25021-08-3, As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

Downstream synthetic route of 25021-08-3

25021-08-3, As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

N-[(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]-L-valyl-N-{3-[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]propyl}-L-alaninamide The title compound was prepared from Example M9 first by coupling with N-[(benzyloxy)carbonyl]-L-valyl-L-alanine in the presence of HATU and N,N-diisopropylethylamine. In the next step, the Z protective group was removed by hydrogenating for 1 hour over 10% palladium on activated carbon at RT under hydrogen standard pressure and then converting the deprotected intermediate into the title compound by coupling with (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N-diisopropylethylamine. LC-MS (Method 1): Rt=1.21 min; MS (ESIpos): m/z=777 (M+H)+.

25021-08-3, As the paragraph descriping shows that 25021-08-3 is playing an increasingly important role.

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;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Simple exploration of 25021-08-3

25021-08-3, 25021-08-3 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid 319935, apyrrolines compound, is more and more widely used in various.

For synthesis of intermediate 1, 398 mg (1.875 mmol) of (E)-4,4?-(diazene-1,2-diyl)dianiline and 726.8 mg (4.7 mmol, 2.5 eq) of 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid were solubilized in a mixture of anhydrousDMF/acetonitrile. We then added 1.108 g (4.7 mmol, 2.5 eq) ofHATU and 0.65 mL of anhydrous triethylamine (4.7 mmol, 2.5 eq). Themixture was agitated at room temperature for 20 h. After extraction(NaHCO3, 3¡Á ethyl acetate), the crude product was washed with acetone.The supernatant was purified by flash-column chromatography (silica)with ethyl acetate and heptane (60:40). An orange product was obtained(compound 1, 51% yield): NMR 1H (acetone-d6):delta (ppm), 9.66 (1H, s), 7.78(2H, d, J = 9.3 Hz), 7.76 (2H, d, J = 9.3 Hz), 7.71 (2H, d, J = 8.9 Hz), 7.01 (2H,s), 6.78 (2H, d, J = 8.9 Hz), and 4.41 (2H, s); NMR 13C (DMSO-d6):delta (ppm),170.64, 165.11, 152.47, 139.70, 138.55, 136.20, 134.95, 128.15, 125.90,123.50, 122.23, 118.86, 112.85, 112.52, 68.49, 55.81, 32.08, and 29.58.For synthesis of MAM-2, 200 mg (0.5725 mmol) of intermediate 1 wasmixed with 112.3 mg (1.145 mmol, 2 eq) of maleic anhydride and heatedunder microwave conditions (110 C, 90 min) in acetone. The obtainedprecipitate was filtered and resuspended in acetone and then heated 5 minat 60 C with 0.12 mL of triethylamine (0.8588 mmol, 1.5 eq). We then added0.54 mL of acetic anhydride (5.725 mmol, 10 eq) with a catalytic amount ofmanganese acetate (III), and the mixture was heated under microwaveconditions (90 min, 110 C). After addition of water and filtration, 46.1 mg ofMAM-2 was obtained (19% yield): NMR 1H (DMSO-d6):delta (ppm), 10.66 (1H, s),7.97 (2H, d, J = 8.8 Hz), 7.92 (2H, d, J = 8.8 Hz), 7.79 (2H, d, J = 8.8 Hz), 7.58(2H, d, J = 8.8 Hz), 7.23 (2H, s), 7.16 (2H, s), and 4.34 (2H, s); NMR 13C (acetone-d6):delta (ppm), 171.30, 170.38, 166.17, 152.11, 149.51, 142.76, 135.71,135.60, 135.25, 127.78, 124.83, 123.80, 120.53, and 41.46; (ESI-HMRS):(m/z,[M+H]+), 429.1073 calculated for C22H15N5O5+; found, 429.1069.

25021-08-3, 25021-08-3 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid 319935, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Harkat, Mahboubi; Peverini, Laurie; Cerdan, Adrien H.; Dunning, Kate; Beudez, Juline; Martz, Adeline; Calimet, Nicolas; Specht, Alexandre; Cecchini, Marco; Chataigneau, Thierry; Grutter, Thomas; Proceedings of the National Academy of Sciences of the United States of America; vol. 114; 19; (2017); p. E3786 – E3795;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

Brief introduction of 25021-08-3

25021-08-3, The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

Trifluoroacetic acid/L-alanyl-N5-carbamoyl-N-(4-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}phenyl)-L-ornithinamide (1:1) The title compound was prepared from 1,4-phenylenediamine sequentially according to classical methods of peptide chemistry. In the first step, 942 mg (8.72 mmol) of 1,4-phenylenediamine were monoacylated with 0.8 g (2.9 mmol) of N2-(tert-butoxycarbonyl)-N5-carbamoyl-L-ornithine in the presence of HATU and N,N-diisopropylethylamine. In the second step, in an analogous manner, the second anilinic amino group was acylated with (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N-diisopropylethylamine. Deprotection with TFA, coupling with 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-alaninate and another deprotection with TFA then gave, in 3 further synthesis steps, the title compound, 148 mg of which were obtained by this route. LC-MS (Method 1): Rt=0.21 min; MS (ESIpos): m/z=474 (M+H)+. LC-MS (Method 4): Rt=0.2 min; MS (ESIpos): m/z=474 (M+H)+.

25021-08-3, The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

Brief introduction of 25021-08-3

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

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)+.

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

Analyzing the synthesis route of 25021-08-3

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.

25021-08-3, 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

200 mg (0.805 mmol) of tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate, 150 mg (0.966 mmol) of (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid and 560 mul (3.2 mmol) of N,N-diisopropylethylamine were dissolved in 10 ml of dimethylformamide, and 459 mg (1.21 mmol) of HATU were added. The reaction mixture was stirred at RT for 30 minutes. The solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed twice with 5% strength citric acid solution and dried over magnesium sulphate, and the solvent was evaporated under reduced pressure. The residue was purified using Biotage Isolera (silica gel, column 25 g SNAP, dichloromethane:methanol 98:2). This gave 276 mg (89% of theory) of tert-butyl {2-[2-(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethoxy)ethoxy]ethyl}carbamate. LC-MS (Method 1): Rt=0.67 min; MS (ESIpos): m/z=386 (M+H)+.

The synthetic route of 25021-08-3 has been constantly updated, and we look forward to future research findings.