Heterocyclic Building Blocks-Pyrrolines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.766-36-9,3-Ethyl-4-methyl-2,5-dihydro-1H-pyrrol-2-one,as a common compound, the synthetic route is as follows.

766-36-9, Compound A is added in a reaction vessel at a mass ratio of 1:6:3-Ethyl-4-methyl-2-pyrrolinone and n-heptane,The mixture was heated to 70¡ãC to dissolve all the solids, and the temperature was controlled at 90-100¡ãC. Compound B: phenylethyl isocyanate was slowly added dropwise with a molar ratio of Compound B to Compound A of 1.5:1, at which temperature the reaction 7 hour,In the HPLC system, the content of compound A was less than 5.0percent. The heating was stopped, and the temperature was lowered to 15¡ã C. with stirring. The second step:Methyl tert-butyl ether and n-heptane were added dropwise to the mixture, and the mixture was stirred at this temperature for 5 hours. The mixture was filtered and the filter cake was mixed with n-heptane:methyl tert-butyl ether ( The mass ratio of 1:1) was washed twice. Each time the amount of compound A was 1 times the mass, and the compound C was dried under vacuum at 45¡ãC.The yield was 90.0percent or more, and the HPLC purity of compound C was greater than 99.5percent.

As the paragraph descriping shows that 766-36-9 is playing an increasingly important role.

Reference£º
Patent; Yangzijiang Pharmaceutical Group Jiangsu Haici Biological Pharmaceutical Co., Ltd.; Guo Weijun; Wang Qinghui; Niu Mingyu; Ma Lijin; Shi Dengjian; (5 pag.)CN107382813; (2017); A;,
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69778-83-2, 4-Methoxy-1H-pyrrol-2(5H)-one is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,69778-83-2

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]

As the paragraph descriping shows that 69778-83-2 is playing an increasingly important role.

Reference£º
Patent; GEMIN X BIOTECHNOLOGIES INC.; WO2006/89397; (2006); A1;,
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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: Synthetic routes of the target compound, pyrene-bisindolylmaleimide (PBM), are outlinedin Scheme 1. The synthesis of PBMstarted from dibromomaleimide (1), whichwas coupledwith two equivalents of 2-methylindole-MgBr and yielded bis-2-methylindolylmaleimide(BM) [10, 11]. Followed by the hydrolysis of 2 in KOH aqueous solution, bis-2-methylindolylmaleic acid anhydride was obtained with the nitrogen atom replaced byoxygen atom [12]. Subsequent imidization of bis-2-methyindolemaleic anhydride with1-aminopyrene yielded the target compound PBM. Bis-2-methylindolylmaleic acid anhydride (50 mg, 0.14 mmol) and 1-aminopyrene(35 mg, 0.16 mmol) dissolved in 2-methoxyethanol (25 mL). Three drops of triethylaminewas added to the solution. The mixture was heated to reflux for about 24 h. The reactionprocess was monitored by TLC. After the bis-2-methylindolylmaleic acid anhydride wasdisappeared. The reactionmixture was cool to ambient temperature and poured to water (25mL). The mixture was extracted with ethyl acetate (25 mL¡Á3). The collected organic phasewas dried over MgSO4. After filtration, the solvent was evaporated in vacuum. The crudeproduct was purified by silica gel column chromatography with ethyl acetate/petroleumether (1:2) as the eluant, affording dark red solid of PBM (61 mg, yield, 78%)., 1122-10-7

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

Reference£º
Article; Li, Xiaochuan; Son, Young-A; Molecular Crystals and Liquid Crystals; vol. 601; 1; (2014); p. 182 – 189;,
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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

Reaction of commercially available Boc-Gly-Gly-Gly-OH (compound 8) with Nhydroxyxuccinimide and EDC coupling agent affords compound 9. Reaction of compound 9 with 1-(2-aminoethyl)-maleimide HC1 in the presence of a base such as diisopropyl ethyl amine (DIPEA) followed by Boc deprotection with HC1 in methoxymethyl ether gives compound 10. Reaction of compound 10 with glutamic anhydride gives compound 11. Reaction of compound 11 with DM? using EDC as coupling agent will give the desired product compound 12.

134272-64-3, The synthetic route of 134272-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; WIDDISON, Wayne, C.; WO2014/134457; (2014); A2;,
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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

MeVal-Val-Dil-Dap-Phe-OtBu (compound 1, 35 mg, 0.044 mmol) was suspended in DMF (0.250 mL). 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid (11 mg, 0.049 mmol) and HATU (17 mg, 0.044 mmol) were added followedby DIEA (0.031 mL, 0.17 mmol). This reaction mixture was allowed to stir for 2.0 hr. HPLC analysis indicated completeconsumption of starting compound 1.[0565] Product was isolated via preparatory RP-HPLC, using a Phenomenex C12 Synergi Max-RP 80A Column (250x 21.20 mm). Eluent: linear gradient 10% to 80% MeCN/0.05% TFA (aq) over 8 minutes, then isocratic 80% MeCN/0.05%TFA (aq) for an additional 12 minutes. A total of 20 mg of pure product (14) was isolated (0.02 mmol, 46% yield). ESMSm/z 987.85 [M+H]+; 1019.41 [M+Na]+; 985.54 [M-H]-., 17057-04-4

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

Reference£º
Patent; Seattle Genetics, Inc.; Doronina, Svetlana O.; Senter, Peter D.; Toki, Brian E.; Ebens, Allen J.; Kline, Toni Beth; Polakis, Paul; Sliwkowski, Mark X.; Spencer, Susan D.; EP2486933; (2015); B1;,
Pyrroline – Wikipedia
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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.

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% 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)+.

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 fields.

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
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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 (0.594 mmol) of tert-butyl (14-amino-3,6,9,12-tetraoxatetradec-1-yl)carbamate, 111 mg (0.713 mmol) of (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid and 410 mul (2.4 mmol) of N,N-diisopropylethylamine were dissolved in 6 ml of dimethylformamide, and 339 mg (0.892 mmol) of HATU were added. The reaction mixture was stirred at RT for 1 h and purified directly by preparative RP-HPLC (column: Reprosil 250*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 130 mg (43% of theory) of tert-butyl [17-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-16-oxo-3,6,9,12-tetraoxa-15-azaheptadec-1-yl]carbamate. LC-MS (Method 1): Rt=0.71 min; MS (ESIpos): m/z=474 (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; 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

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.

EDCI .HCI (0.13 g, 0.66 mmol, 1 .1 eq.) was added to a cloudy solution of compound 21 (0.61 g, 0.6 mmol, 1 .0 eq.) and Mal-dPEG8-OH (0.393 g, 0.66 mmol, 1 .1 eq.) in CHCI3 (25 mL). The clear solution was stirred at room temperature for 1 .5h., diluted with CHC (100 mL) washed with brine (2 x 100 mL), dried (MgS04) and evaporated under reduced pressure to give a yellow foam. Purification by flash column chromatography [CHCb/MeOH 0% to 6% in 1 % increments gave the product as a white foam (0.786 g, 82%). Analytical Data: RT 1 .44 min; MS (ES+) m/z (relative intensity) 1586 {[M + H]+ ,40), 1609 {[M + Na]+ , 100)

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

Reference£º
Patent; MEDIMMUME LIMITED; HOWARD, Philip Wilson; DUNNY, Elizabeth; MASTERSON, Luke; (151 pag.)WO2017/137553; (2017); A1;,
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1193-54-0, 3,4-Dichloro-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 2-(7-methoxynaphthalen-1-yl)ethanamine (compound 3, 101 mg, 0.5 mmol), sodium acetate (82 mg, 1.0 mmol) and cyclic anhydrides 1.0 mmol) in 5mL acetic acid was heated to reflux for 3 h in a round bottomed flask. After the completion of reaction (as evidenced by TLC), the resulting mixture was concentrated under reduced pressure and washed with ethyl acetate (10 mL¡Á3), then the concentrated organic layer was purified by column chromatography on silica gel to obtain pure product., 1193-54-0

As the paragraph descriping shows that 1193-54-0 is playing an increasingly important role.

Reference£º
Article; Chang, Ying; Pi, Weiyi; Ang, Wei; Liu, Yuanyuan; Li, Chunlong; Zheng, Jiajia; Xiong, Li; Yang, Tao; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1672 – 1676;,
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1-Pyrroline | C4H7N – PubChem

6913-92-4,6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Cyanonitrone 13 (550 mg, 3.44 mmol) and N-benzyl-3-pyrroline2 (1.3 mL, 6.83 mmol) were dissolved in toluene (4 mL) and themediumwas stirred for 2 h at 80 C under micro-waves irradiation.The solvent was removed under reduced pressure before purificationby silica gel column chromatography (eluent: EtOAc/toluene 1/10). This allowed the separation of a minor more mobileregioisomer (60 mg, 6%) from the main racemic cycloadduct expected(¡À)-17 (500 mg, 45%). Compound (¡À)-17: Yellowish oil.Rf 0.4 (1:4 EtOAc/toluene). 1H NMR (500 MHz, 80 C, toluene-d8)d 7.4e7.0 (m, 10H, HeAr), 4.28 (ddd, 1H, J 3.4 Hz, J 6.0 Hz,J 7.5 Hz, H-4), 4.15 (d, 1H, J 13.4 Hz, H-8), 3.80 (d, 1H, J 13.4 Hz,H-8), 3.29 (d, 1H, J 13.1 Hz, H-9), 3.23 (d, 1H, J 13.1 Hz, H-9), 3.07(d, 1H, J 3.6 Hz, H-6), 2.79 (ddd, 1H, J 4.0 Hz, J 7.8 Hz,J 11.6 Hz, H-3), 2.48 (dd, 1H, J 3.1 Hz, J 10.1 Hz, H-50), 2.22 (br s,1H, H-5), 2.17 (br m, 1H, H-20), 2.09 (br m, 1H, H-2). 1D NOE experimentswith selective irradiations (H-3, H-4, or H-6), showedsignals enhancements as follows: H-3 irradiation: enhancements ofH-2: 2.5%, H-2?: 1.9%, H-4: 2%, H-6: 1.1%; irradiation of H-4: enhancementsof H-3: 2.1%, H-5: 1.9%, H-5?: 1.4%; irradiation of H-6:enhancements of H-2: 2%, H-2?: 1.8%. 13C NMR (126 MHz, 80 C,toluene-d8): d 139.8 (Caear), 137.2 (Ca?-ar), 130.2, 129.5, 129.4,129.3, 128.6, 128.1 (10C-ar), 116.9 (C-7), 81.9 (C-4), 60.0 (C-9), 59.9(C-6), 59.8, 59.7 (C-5, C-8), 57.5 (C-2), 53.6 (C-3). HRMS-ESI, positivemode: m/z calcd for C20H22N3O [MH]: 320.1757; found:320.1767.Compound (¡À)-18: yellow clear oil. Rf 0.6 (1/4 EtOAc/toluene).1H NMR (500 MHz, toluene-d8) d 7.5e7.0 (m, 10H, HeAr), 4.40 (dd,1H, J 4.7 Hz, J 7.7 Hz, H-4), 3.71 (d, 1H, J 8.1 Hz, H-6), 3.39 (s,2H, H-9), 3.20 (d, 1H, J 17.2 Hz, H-7), 3.01 (d, 1H, J 10.8 Hz, H-50),2.77 (d, 1H, J 17.2 Hz, H-7), 2.71 (d, 1H, J 9.7 Hz, H-20), 2.64 (app.q, 1H, J 7.3 Hz, H-3), 1.73 (m, 2H, H-2, H-5). 13C NMR (126 MHz,toluene-d8) d 140.02 (Caear), 138.41 (Ca?-ar), 129.84,129.35, 129.35,129.31, 128.93, 128.02 (10C-ar), 115.00 (C-8), 82.19 (C-4), 76.02 (C-6), 59.54 (C-9), 59.28 (C-5), 58.04 (C-3), 56.60 (C-2), 42.16 (C-7). 2DNMR (HMBC) showed correlations between H-6 and aromaticcarbons, as well as correlations between methylene H-7 and C-8 inthe nitrile group. 1D NOE experiments with selective irradiations(H-3, H-4, or H-6), showed signals enhancements as follows: H-3irradiation: enhancements of H-2: 4.6%, H-4: 4.2%, H-6: 1.1%, HeAr:3.5%; irradiation of H-4: enhancements of H-3: 3.8%, H-5: 4.1%, H-5?: 1.2%; irradiation of H-6: enhancements of H-2?: 2.9%, H-5?: 0.3%,HeAr: 5.4%. HRMS-ESI, positive mode: m/z calcd for C20H22N3O[MH]: 320.1757; found: 320.1750.

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

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;,
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