Heterocyclic Building Blocks-Pyrrolines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

Trifluoroacetic Acid/4-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]pyrrolidine-3-carboxamide (1:1) 40.5 mg (0.06 mmol) of 4-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (Intermediate C25) and 14.5 mg (0.08 mmol) of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (1:1) were initially charged in 1.0 ml of acetonitrile, and 64.4 mg (0.51 mmol) of N,N-diisopropylethylamine and 50.0 mg (0.08 mmol) of T3P were added and the mixture was stirred at RT for 16 h. The same amount of 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (1:1), N,N-diisopropylethylamine and T3P were added again, and the mixture was stirred at RT for a further 4 h. The reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 125*30; 10mu, flow rate: 50 ml/min, MeCN/water). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 7.2 mg (15% of theory) of the compound tert-butyl 3-{[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]methyl}-4-{[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamoyl}pyrrolidine-1-carboxylate. LC-MS (Method 1): Rt=1.30 min; MS (ESIpos): m/z=763 [M+H]+.

The synthetic route of 134272-64-3 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

1122-10-7, 3,4-Dibromo-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The reaction was carried out under strictly dry conditions.To triphenylphosphine (193.9 mg, 0.7 mmol) in THF (5 mL)was added drop-wise diisopropyl azodicarboxylate (145.6 jii,0.7 mmol) at -78 C. The reaction was stirred for 5 mm andPEG300 (200.0 mg, 0.6 mmol) in THF (4 mL) was addeddrop-wise. The reaction was stirred for 5 mm and neopentylalcohol (45.8 mg, 0.5 mmol) in THF (1 ml) was added. Thereaction was stirred for 5 mm and 3,4-dibromomaleimide(189.4mg, 0.7 mmol) in THF (2 ml) was added. The reactionwas stirred for 10 mm, the cold bath removed and stirred for20 h at ambient temperature. The solvent was removed invacuo and the residual material was purified by flash chromatography on silica gel (methanol:dichloromethane, gradientelution from 0.5-5.0% methanol). Fractions containing theproduct were collected and the solvent was removed in vacuo.The still impure product was purified by flash chromatograss phy on silica gel (petroleum ether: ethyl acetate, gradientelution from 7:3 to 2:8) to afford the desired compound as ayellow oil (137 mg, 40%) with 97.5% purity. ?H NMR (500MHz, CDC13): oe=3.76 (t, 2H, J=5.6, N-CH2), 3.64-3.52 (m,24H, 12xCH2-O), 3.49 (t, 2H, J=4.4, N-CH2—CH2), 3.32(s, 3H, O-CH3); ?3C NMR (125 MHz, CDC13): oe=163.8(2xC), 129.5 (2xC), 72.0 (CH2), 70.7-70.5 (9xCH2), 70.1(2xCH2), 67.5 (CH2), 59.1 (CH3), 39.0 (CH2); IR (solid,cm?): 3496 (w), 2869 (m), 1786 (m), 1720(s), 1594 (m); MS(CI) mlz, (%): 580 (8?M+H, 12), 578 (81 79M+H, 23), 576 (79M+H, 12), 279 (100), 84 (61); Mass calc. for C,9H3 ,7913r2O9N[+H]: 576.0444. Found: 576.0437.

The synthetic route of 1122-10-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCL Business Plc; Smith, Mark; Caddick, Stephen; Baker, James; Chudasama, Vijay; (80 pag.)US9295729; (2016); B2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1334177-86-4,1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16,19,22,25,28-octaoxa-4-azahentriacontan-31-oic acid,as a common compound, the synthetic route is as follows.

N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide (28 mg, 0.146 mmol, 1 eq) was added to a solution of 105 (203 mg, 0.146 mmol) and maleimide-PEG8 acid (87 mg, 0.146 mmol) in chloroform (5 mL). The reaction was stirred for 1 .5 h then diluted with chloroform (50 mL), washed with water (50 mL), brine (30 mL), dried over magnesium sulphate, filtered and evaporated. Flash chromatography [gradient elution 100% DCM to 90% DCM/10% methanol] gave 106 as a pale yellow solid (205 mg, 72%). LC/MS: RT 5.75 min; MS (ES+) m/z (relative intensity) 982.90 (100), 1963.70 (5).

1334177-86-4 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16,19,22,25,28-octaoxa-4-azahentriacontan-31-oic acid 51340955, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; VAN BERKEL, Patricius Hendrikus Cornelis; HOWARD, Philip Wilson; (283 pag.)WO2016/166298; (2016); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.151038-94-7,6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate,as a common compound, the synthetic route is as follows.

[00393] A solution of FK506 (1) (0.1 g, 124.4 mumol), 6-maleiimidocaproic hydrazide trifluoroacetate (2) (0.126 g, 373.2 mumol) and trifluoroacetic acid (catalytic, 1 muL) in anhydrous methanol (5 mL) was stirred at room temperature for 36 h. The reaction was monitored by thin layer chromatography that showed almost complete disappearance of the starting material. [TLC solvent system-dichloromethane (95): methanol (5), Rf=0.3]. The reaction mixture was concentrated to dryness and dissolved in ethyl acetate (20 mL). The organic layer was washed with water and 10% sodium bicarbonate solution and then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography using dichloromethane (96): methanol (4) as eluent to give the hydrazone 3 (0.116 g, 92%).

151038-94-7 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate 23509306, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; CellGate, Inc.; US6669951; (2003); B2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1122-10-7,3,4-Dibromo-1H-pyrrole-2,5-dione,as a common compound, the synthetic route is as follows.

A methanol solution (20 mL) of sodium acetate (360 mg,4.39 mmol) and propanethiol (304 mg, 4.00 mmol) was dropwisedinto a methanol solution (16 mL) of 2,3-dibromomaleimide (2.04 g,8 mmol)over 1 h. On completion of addition, the solution was stirredat room temperature for another 3 h. After that, the solutionwas concentrated and the crude product was purified by columnchromatography (SiO2, petroleum ether/ethyl acetate = 3/1) to producethe yellow solid product (520 mg) with a yield of 52%.

1122-10-7 3,4-Dibromo-1H-pyrrole-2,5-dione 14279, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Long, Shiyu; Tang, Qingquan; Wu, Ying; Wang, Luoxin; Zhang, Ke; Chen, Yongming; Reactive and functional polymers; vol. 80; 1; (2014); p. 15 – 20;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

Preparation of the Compound I.1: (alphaS,3R,4S) 4-hydroxy alpha-amino acetic 3-pyrrolidine acid or (alphaS,3R,4S) alpha-amino-(4-hydroxy-pyrrolidin-3-yl)acetic acid Cycloaddition of the nitrone 1 (corresponding to the compounds of formula (III)) on commercial N-Bn-3-pyrroline 2 (corresponding to the compounds of formula (IV)): synthesis of 3 (corresponding to the compounds of formula (II)): The nitrone 1 (392 mg, 1.64 mmol) [24, 25] and commercial N-Bn-3-pyrroline 2 in excess (314 mg, 1.97 mmol, 1.2 equiv.) are introduced into a flask adapted to a Biotage Initiator microwave reactor. After having filled the flask with argon, 2.5 ml of anhydrous toluene are poured therein. The flask, sealed with a septum and mounted in the microwave apparatus is irradiated with the instruction of maintaining a temperature of 140 C. for 2 h in order to totally convert the nitrone 1. Once the flask is cooled, the reaction crude product is concentrated and then purified by flash chromatography on a silica column (ethyl acetate) in order to lead to the cycloadduct 3 (625 mg, 1.57 mmol) with a yield of 96% and total stereoselectivity (the reaction was conducted on a scale of 5 grams with similar results). Single crystals of the compound 3 were obtained from a diethyl ether solution saturated with 3, left in the cold (freezer). Rf=0.48 (EtOAc). [alpha]D=+40.4 (c 1.1, CH2Cl2). 1H NMR (400 MHz, CDCl3): delta 7.37-7.20 (m, 5H, CH-ar), 4.59 (td, J=7.0 Hz, J=3.0 Hz, 1H, H-4), 3.71-3.49 (m, 3H, NCH2Ph, H-6), 3.42 (dd, J=10.3 Hz, J=6.6 Hz, 1H, H-3), 2.78 (dd, J=10.3 Hz, J=3.0 Hz, 1H, H-5), 2.75-2.69 (m, 4H, NCH3, H-2), 2.65 (dd, J=9.4 Hz, J=3.7 Hz, 1H, H-2′, 2.58 (dd, J=9.9 Hz, J=6.6 Hz, 1H, H-5′, 2.14-2.08 (m, 1H, H-9), 2.00 (dtt, J=12.9 Hz, J=6.5 Hz, J=3.3 Hz, 1H, H-10), 1.90-1.78 (m, 2H, H-11, H-12), 1.68-1.59 (m, 1H, H-12′), 1.48 (dt, J=13.5 Hz, J=6.7 Hz, 1H, H-15), 1.38 (dd, J=12.1 Hz, J=3.2 Hz, 1H, H-13), 1.18 (t, J=12.3 Hz, 1H, H-9′), 0.95-0.85 (m, 10H, H-11′, H-14, H-16) ppm. 13C NMR (100 MHz, CDCl3): delta 172.8 (C=O), 138.9 (CIV-ar), 128.6 (CH-ar), 128.3 (CH-ar), 127.1 (CH-ar), 88.0 (C-8), 79.6 (C-4), 71.9 (C-6), 59.6 (NCH2Ph), 59.4 (C-5), 59.3 (C-2), 49.1 (C-3), 48.2 (C-13), 41.0 (C-9), 35.0 (C-11), 29.0 (C-10), 25.9 (NCH3), 24.5 (C-15), 24.2 (CH3), 22.6 (C-12), 22.4 (CH3), 18.7 (CH3) ppm. HR-ESI-QToF MS (positive method): m/z calcul. for C24H36N3O2 [M+H]+ 398.2802. found 398.2806.

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; Praly, Jean-Pierre; Aouadi, Kaiss; Cecioni, Samy; Denoroy, Luc; Parrot, Sandrine; US2015/175537; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

NHS ester 5a (8.2 mg, 7.6 muiotaetaomicron) and l-(2-aminoethyl)- lH-pyrrole-2,5-dione hydrochloride (2.2 mg, 0.011 mmol) were dissolved in anhydrous dichloromethane (305 ) at room temperature. DIPEA (2.66 mu, 0.015mmol) was added and the reaction and was stirred for 3.5 hours. The reaction mixture was concentrated and was purified by RPHPLC (CI 8 column, CH3CN/H2O, gradient, 35% to 55%). The desired product fractions were frozen and lyophilized to give maleimide, compound D5 as a solid white powder (5.3 mg, 58% yield). LCMS = 5.11 min (8 min method). MS (m/z): 1100.6 (M + 1)+.

134272-64-3 N-(2-Aminoethyl)maleimide Hydrochloride 22118207, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; IMMUNOGEN, INC.; YODER, Nicholas, C.; BAI, Chen; MILLER, Michael, Louis; (179 pag.)WO2017/4025; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

1334177-86-4, 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16,19,22,25,28-octaoxa-4-azahentriacontan-31-oic acid is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The imine 17 (92 mg, 0.1 mmol, 1.1 equiv.) was dissolved in CHCI3 (6 ml.) with one drop of anhydrous MeOH to aid dissolution. Maleimide-PEG8-acid (53 mg, 0.09 mmol, 1 equiv.) was added followed by EEDQ (33 mg, 0.14 mmol, 1 .5 equiv.). This was left to stir vigorously at room temperature under Ar for 4 days until LC/MS analysis showed majority product formation. The solvent was removed in vacuo and the crude product was partially purified by silica gel column chromatography (CHCI3 with 1 % to 10% MeOH gradient) yielding 18 (81 mg). The material was purified further by preparative HPLC (method 2) to give 18 as a yellow solid (26.3 mg, 18%). Fast Formic run: LC/MS (method 3)(1 .39 min (ES+) m/z (relative intensity) 1485.00 ([M + H]+., 64).

As the paragraph descriping shows that 1334177-86-4 is playing an increasingly important role.

Reference£º
Patent; SPIROGEN SARL; HOWARD, Philip Wilson; WO2014/57072; (2014); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1122-10-7,3,4-Dibromo-1H-pyrrole-2,5-dione,as a common compound, the synthetic route is as follows.

To 2.5 g of 3,4-dibromo-1H-pyrrole-2,5-dione (10 mmol) and 1 g of NMM in 60 mE of THF, MeOCOC1 (10 mmol, 940 mg in 10 ml DCM) was added dropwise, stirred for 20 mm, then the reaction solution was diluted with 60 mE of DCM, washed 3 time by water, the organic phase was stirred by sodium sulfate anhydrous, concentrated, 2.65 g of methyl 3,4-dibromo-2,5-dioxo-2H-pyrrole-1 (5H)-carboxy- late was obtained. To 311 mg, 1 mmol of this compound, 2-(2-azidoethoxy)ethanamine (130 mg, 1 mmol) and 5 mE DCM was added, TEC shown the reaction finished in 20 mm, then extracted by DCM and brine, washed by NH4C1 solution, dried on sodium sulfate anhydrous, and then concentrated for column purification, flashed by 2:1 hexane and ethyl ethylate, 230 mg of 1 -(2-(2-azidoethoxy)ethyl)-3,4- dibromo-1 H-pyrrole-2,5-dione obtained. ?HNMR: 3.32 ppm (t, J=5.0 Hz, 1H), 3.40 ppm (t, J=5.0 Hz, 1H), 3.50 ppm (q, J=5.0 Hz, 1H), 3.62 ppm (t, J=5.0 Hz, 1H), 3.63-3.69 ppm (m, 3H), 3.84 ppm (t, J=5 hz, 1H). Fw: 365.9, C8H8Br2N403 Mass Peaks (1:2:1): 366.9, 368.9, 370.9

1122-10-7 3,4-Dibromo-1H-pyrrole-2,5-dione 14279, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; Sorrento Therapeutics, Inc.; Fu, Yanwen; Kaufmann, Gunnar F.; Patterson, James T.; (43 pag.)US2017/137539; (2017); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17057-04-4,4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid,as a common compound, the synthetic route is as follows.

Derivative 1 was synthesized using a modified procedure reported by Willner etal. [51] as it is also described by Lau etal. [31]. A cooled suspension (0 C) of molecule 4 (211 mg, 0.97 mmol) in methylene chloride (4.5 mL) was treated with triethylamine (190 muL, 1.36 mmol) and isobutyl chloroformate (175 muL, 1.34 mmol). The mixture was stirred for 1 h at 0 C and at room temperature (22 C) for about 1 h. Afterwards, tert-butyl carbazate (128 mg, 0.97 mmol) dissolved in methylene chloride (0.8 mL) was added dropwise to the mixture and stirred for an additional 12 h at 22 C. The reaction mixture was diluted with ethyl acetate (55 mL) and methylene chloride (20 mL) and washed twice with saturated NaHCO3 (2 ¡Á 50 mL), twice with 0.1 N HCI (2 ¡Á 50 mL), twice with saturated NaCl (2 ¡Á 50 mL), and finally with H2O (50 mL). The organic phase was dried (MgSO4) and evaporated to give crude derivative 1. The product was purified by flash chromatography, using a mixture of hexanes/acetone (3/2), to yield 173 mg (54 %) of 1.

17057-04-4 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid 86925, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Hamelin-Morrissette, Jovane; Cloutier, Suzie; Girouard, Julie; Belgorosky, Denise; Eijan, Ana Maria; Legault, Jean; Reyes-Moreno, Carlos; Berube, Gervais; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 259 – 268;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem