Heterocyclic Building Blocks-Pyrrolines

6913-92-4,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.

N-Benzyl-3-pyrroline 2 (504 muL, 2.64 mmol) was added to a solution of ethyl chlorooximidoacetate (1 g, 6.62 mmol, 2.5 eq) in toluene (20 mL). The flask was heated to 110 C (oil bath) while a solution of Et3N (276.8 muL, 19.8 mmol, 7.5 eq) in toluene (15 mL) was added over 16 hh using a syringe pump. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography (4:1 petroleum ether/EtOAc) to afford compound (+-)-20 (370 mg, 1.35 mmol, 51%). Yellow oil Rf = 0.52 (7:3 petroleum ether/EtOAc). 1H NMR (400 MHz, CDCl3): delta 7.26 (m, 5H, phenyl), 5.20 (dd, 1H, J5,4 = 4.5 Hz, J3,4 = 9.6 Hz, H-4), 4.31 (2 complex q, 2H, J = 7.2 Hz, diastereotopic OCH2), 3.91 (dt, 1H, J2′,3 = 1.0 Hz, J2,3 = 7.1 Hz, J3,4 = 9.5 Hz, H-3), 3.68 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.55 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.24 (d, 1H, 2J = 11.2 Hz, H-5′), 3.19 (d, 1H, 2J = 9.9 Hz, H-2′), 2.44 (dd, 1H, J2,3 = 7.2 Hz, 2J = 9.8 Hz, H-2), 2.37 (dd, 1H, J5,4 = 4.6 Hz, 2J = 11.2 Hz, H-5), 1.31 (t, 3H, J = 7.2 Hz, Me). 13C NMR (100 MHz, CDCl3): delta 160.7, 152.2 (C=N, C=O), 137.8 (C-ar), 128.5 (2CH-ar), 128.2 (2CH-ar), 127.1 (1CH-ar), 87.4 (C-4), 61.9 (OCH2), 61.1 (C-5), 58.3 (CH2 benzyl), 56.9 (C-2), 51.0 (C-3), 14.1 (CH3). MS m/z = 274.13 for C15H18N2O3; MS-ESI positive mode: 275.1 [M+H]+, 297.1 [M+Na]+.

The synthetic route of 6913-92-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
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.205444-34-4,(S)-tert-Butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

Boron tribromide (BBr3 12 ml; 1 M in CH2Cl2) was slowly added to a stirred solution of 3-Iodo-5-methoxypyridine (10, 471 mg; 2 mmol) in CH2Cl2 (10 ml) at -40 C (dry ice bath) and reaction mixture was left overnight stirring with gradual warming to ambient temperature. MeOH (7 ml) was slowly added and the reaction mixture was refluxed for 2 h. After removal of solvent, water was added and pH was adjusted to 7-8 by adding Na2CO3. The reaction mixture was extracted with EtOAc, dried over Na2SO4 and concentrated to yield crude product which was purified by prep-TLC using EtOAc/hexanes (1:3) to furnish 3-iodo-5-hydroxypyridine, 11 (300 mg, 68%) as a solid compound. To a solution of 6 (0.20 g, 1.0 mmol), 3-iodo-5-hydroxypyridine (11, 0.24 g, 1.1 mmol) and triphenylphosphine (0.40 g, 1.5 mmol) in THF (10 mL), stirred under argon and cooled at 0 C, was added diisopropyl azodicarboxylate (DIAD; 0.3 mL, 1.5 mmol). The reaction mixture was allowed to come up to ambient temperature over a period of 2 h and was stirred overnight. The reaction mixture was evaporated to dryness and the residue was purified by preparative TLC (30% EtOAc in hexane) to give pure product 12 (0.20 g, 50%) as an oil. 1H NMR (500 MHz, CDCl3) delta ppm: 8.41(d, J = 15.0, 1H, PyH), 8.25 (d, J = 2.0, 1H, PyH), 7.56 (d, J = 18.5, 1H, PyH), 5.88 (m, 2H, olefinic), 4.80 (m, 1H, CH-CH2), 4.34-3.95 (m, 4H, O-CH2, N-CH2), 1.48 (s, 9H, Boc). MS, m/z, 403 (100%, [M+H]+).

205444-34-4, As the paragraph descriping shows that 205444-34-4 is playing an increasingly important role.

Reference£º
Article; Pandey, Suresh K.; Pan, Shawn; Kant, Ritu; Kuruvilla, Sharon A.; Pan, Min-Liang; Mukherjee, Jogeshwar; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7610 – 7614;,
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.

23.0 mL (2216.4 mmol) of toluene, 5.0 g (22.8 mmol) of 4-maleimidebenzoic acid, 2.2 mL (30.4 mmol) of thionyl chloride, and 4 mL of toluene were placed in a 100 mL three-necked flask equipped with a stirrer and a cooling tube,0.36 mL (4.6 mmol) of N, N-dimethylformamide was added,And the mixture was stirred at 80 DEG C for 1 hour in a nitrogen atmosphere to complete the chlorination reaction. Thereafter, the volatile components were removed by distillation under reduced pressure,Maleimide benzoic acid chloride was obtained as yellowish white crystals.Then, 5.4 g (22.8 mmol) of the obtained 4-maleimide benzoic acid chloride,40.0 mL (353.7 mmol) of O-dichlorobenzene,2.0 g (5.7 mmol) of the compound (1)3.2 mL (22.8 mmol) of triethylamine was stirred for 1 hour while heating at 80 DEG C under a nitrogen atmosphere to complete the esterification reaction. Thereafter, the reaction solution was cooled to room temperature, the precipitate was collected, washed with methanol, and dried to obtain 4.1 g (5.5 mmol) of the compound (2) as yellowish white crystals. The obtained compound (2) was identified by chemical analysis to have a chemical structure represented by the following formula (1-1) (molecular weight: 748.7). It was also confirmed that the compound (2) exhibited thermotropic liquid crystallinity by observation under a polarizing microscope. Further, it was confirmed that the compound (2) showed good solubility in DMSO, DMF and NMP.

17057-04-4, The synthetic route of 17057-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Da I Sel Co., Ltd.; Na Ka-ta-ni-, -go-u-ji; I No-u-e-, -ge-i-jo; (17 pag.)KR2018/130526; (2018); A;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

17057-04-4, 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Equimolar quantities of maleimide (2) and nitrones (5a-k and 6a-k) were refluxed in toluene (20 ml) and ethyl alcohol (5 ml) for 8-10 h (TLC monitoring using petroleum ether and hexane 1:1) followed by cooling with addition of dry ether. The products (7a-k and 8a-k) were separated out after filtration and recrystallized from toluene and petroleum ether mixture (1:1) to yield cis-isomers (7aa-7ka and 8aa-8ka). The mother liquor on further work up provided trans-isomers which were recrystallized from ethanol and diethyl ether mixture (1:1) (7aa’-7ka’ and 8aa’-8ka’) (Fig. 3).7 These stereoisomers were characterized by their 1H NMR, IR and mass spectra in addition to their melting points and elementary analysis. These stereoisomers have identical IR spectra and elemental analysis but differ in their melting points, 1H NMR and mass spectra.

17057-04-4, As the paragraph descriping shows that 17057-04-4 is playing an increasingly important role.

Reference£º
Article; Anand, Preet; Singh, Baldev; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 521 – 530;,
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,1122-10-7

The 2,3-dibromomaleimide (2.55 g, 10.0 mmol) was placed in a 100 mL three-necked flask,Dissolved in 30 mL of dry DMF,Nitrogen protection, down to 0 C,Sodium hydride was added in two portions(480 mg, 12 mmol, 60% mass fraction in paraffin). After 1 h, 10 mL of dry DMF dissolved chloromethylbenzyl ether (2.08 mL, 15 mmol) was added,Rose to room temperature reaction 2h.After the drop to 0 C, adding 20 mL of saturated ammonium chloride solution to stop the reaction,Ethyl acetate, and the organic phase was dried over anhydrous sodium sulfate and concentrated.Column separation by petroleum column: Ethyl acetate = 50: 1 (v / v) eluting the compound4-benzyloxymethyl-2,3-dibromomaleimide 3.55 g, 94% yield.Magnesium wire (432 mg, 18.0 mmol) was placed in 100 mL dry three-necked flask,Add 4 mL of dry tetrahydrofuran, replace with argon,After the introduction of ethyl bromide (1.35 mL, 18.0 mmol)After reaction at room temperature for 15 min, the reaction was brought to 40 C for 30 min.The indole (2.11 g, 18.0 mmol) was introduced via a catheter for 1 h.Followed by the addition of N-benzyloxymethyl-2,3-dibromomaleimide (3.29 g, 8.9 mmol)Room temperature reaction 4h.The reaction was terminated by the addition of 20 mL of saturated ammonium chloride solution, extracted with ethyl acetate,The organic phase was dried over anhydrous sodium sulfate and concentrated. The column was separated by column chromatography,Petroleum ether: ethyl acetate = 4: 1 (v / v) to give 3.46 g of compound 185a in 94% yield.

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

Reference£º
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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.

Piperidine (0.2 mL) was added to a solution of 90 (77 mg, 63.4 mumomicronIota) in DMF (1 mL). The reaction mixture was allowed to stir for 20 minutes. The reaction mixture was carefully diluted with DCM (50 mL) and washed with water (50 mL). The organic layers was washed with brine (100 mL), dried over MgSO4, filtered and evaporated under reduced pressure to provide the unprotected valine intermediate. The crude residue was immediately redissolved in chloroform (5 mL). Mal(Peg)8-acid (56 mg, 95 mumomicronIota) and EDCI (18 mg, 95 mumomicronIota) were added, followed by methanol (0.1 mL). The reaction was allowed to stir for 3 hours at room temperature at which point completion was observed by TLC and LC/MS (1 .19 min (ES+) m/z (relative intensity) 784.25 (([M + 2H] 2+)/2, 100)). The reaction mixture was diluted with chloroform (50 mL), washed with water (100 mL), dried (MgS04), filtered and evaporated in vacuo, followed by high vacuum drying, to provide the crude product. Purification by flash chromatography (gradient elution: HPLC grade 96:4 v/v CHCl3/MeOH to 90:10 v/v CHCl3/MeOH) gave 91 as a yellow solid (43 mg, 43%). 1H NMR (400 MHz, CDCI3) delta 8.73 (s, 1 H), 7.88 (dd, J = 7.6, 3.9 Hz, 2H), 7.75 (d, J = 8.6 Hz, 2H), 7.52 (d, J = 2.0 Hz, 2H), 7.44 (s, 1 H), 7.40 – 7.28 (m, 4H), 6.91 (d, J = 8.8 Hz, 2H), 6.81 (s, 2H), 6.69 (s, 2H), 6.48 (s, 1 H), 4.72 – 4.63 (m, 1 H), 4.46 – 4.34 (m, 2H), 4.25 – 4.03 (m, 6H), 3.95 (s, 4H), 3.84 (dd, J = 17.2, 10.1 Hz, 4H), 3.72 – 3.46 (m, 30H), 3.44 – 3.32 (m, 4H), 3.30 – 3.20 (m, 4H), 2.75 – 2.63 (m, 1 H), 2.59 (s, 4H), 2.55 – 2.43 (m, 3H), 2.37 (s, 3H), 2.29 (dd, J = 12.7, 6.7 Hz, 1 H), 2.03 – 1 .89 (m, 4H), 1 .72 (d, J = 22.7 Hz, 8H), 1 .46 (d, J = 7.2 Hz, 3H), 1 .01 (dd, J = 1 1 .5, 6.9 Hz, 6H). MS (ES+) m/z (relative intensity) 784.25 (([M + 2H] 2+)/2, 100)., 1334177-86-4

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

Reference£º
Patent; VAN BERKEL, Patricius Hendrikus Cornelis; HOWARD, Philip Wilson; (281 pag.)WO2016/166341; (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.17057-04-4,4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid,as a common compound, the synthetic route is as follows.

A mixture of 4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)benzoic acid (30mg, 0.128mmol) and thionyl chloride (10mL) was refluxed overnight at 80C. Unreacted thionyl chloride was evaporated to yield the residual product N-[4-(chlorocarbonyl) phenyl] maleimide (4) which was used directly.

17057-04-4, 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 fields.

Reference£º
Article; Shu, Hai; Wu, Xiaolei; Zhou, Baojing; Han, Yingbin; Jin, Mingjie; Zhu, Jing; Bao, Xiaofeng; Dyes and Pigments; vol. 136; (2017); p. 535 – 542;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

134272-64-3, N-(2-Aminoethyl)maleimide Hydrochloride is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(0436) (0437) To a suspension of the free thiol, 3a (88 mg, 0.105 mmol) and 1-((2,5-dioxopyrrolidin-1-yl)oxy)-1-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid (64.0 mg, 0.158 mmol) in anhydrous dichloromethane (2.10 mL) was added DIPEA (55.0 muL, 0.315 mmol) under nitrogen at room temperature. The mixture stirred for 16 hours and then 1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride (55.6 mg, 0.315 mmol), anhydrous dichloromethane (1.0 mL) and DIPEA (0.055 mL, 0.315 mmol) were added. The mixture stirred for an additional 5 hours at room temperature upon which the reaction was concentrated in vacuo. The resulting residue was purified by RP-HPLC (C18, CH3CN/H2O). Fractions containing desired product were frozen and lyophilized to give maleimide, compound D3 (20 mg, 16% yield) as a white solid. LCMS=4.92 min (8 min method). MS (m/z): 1158.6 (M+1)+.

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

Reference£º
Patent; IMMUNOGEN, INC.; Hilderbrand, Scott A.; Hutchins, Benjamin M.; (94 pag.)US2018/208562; (2018); 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.

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., 1122-10-7

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

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;,
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

General procedure: Dibromomaleimide 1a, 2.0 g (7.84 mmol), was dissolved in 15 mL of anhydrous DMF, and 0.9 mL (9.51 mmol) of 4-fluoroaniline and 2 mL (11.5 mmol) of DIPEA were added. The mixture was stirred for 24 h at 50C and poured into a mixture of water and ethyl acetate. The organic layer was separated, washed with dilute aqueous HCl, and evaporated under reduced pressure, and the residue was purified by column chromatography using petroleum ether-ethyl acetate (5 : 1) as eluent.

1122-10-7, As the paragraph descriping shows that 1122-10-7 is playing an increasingly important role.

Reference£º
Article; Panov; Simonov, A. Yu.; Korolev; Russian Journal of Organic Chemistry; vol. 55; 12; (2019); p. 1847 – 1852; Zh. Org. Khim.; vol. 55; 12; (2019); p. 1850 – 1856,7;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem