Heterocyclic Building Blocks-Pyrrolines

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.

6913-92-4, A mixture of 0.675 g (3.14 mMol) 7-bromo-5-fluorobenzofuran, 5.0 g (31.40 mMol)1-benzyl-3-pyrroline, 2.19 mL (12.56 mMol), N,N-diisopropylethylamine, 0.399 g (9.42 mMol) LiCl, 0.154 g (0.66 mMol) tri-2-furylphosphine, and 0.070 g (0.314 mMol) palladium diacetate in 10 mL N,N-dimethylformamide was heated under nitrogen at 100C for 48 hours. The mixture was diluted with 10 mL diethyl ether and filtered through celite. The filtrate was concentrated under reduced pressure and the oily residue was submitted to kugelrohr distillation to remove most of the pyrrole and pyrrolidine side-products. Flash chromatography of the residue (Et3N/Et2O/hexane 1:39:60) yielded 1-benzyl-3-(5-fluorobenzofur-7-yl)pyrrolidine (173 mg, 19%) as a colorless oil. HRMS calculated for C19H19FNO: 296.1450; found: 296.1437

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

Reference£º
Patent; ELI LILLY AND COMPANY; EP1204659; (2003); B1;,
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.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, In a 500 mL round bottom flask, diethyl pyrrole aldehyde 5 (2.53 g, 9.04 mmol) and 3-ethyl-4-methyl-1H-pyrrol-2-one (1.12 g, 9.04 mmol) were dissolved in 4 M KOH (100 mL) and methanol (25 mL). The reaction mixture was heated at reflux for 4 h, then stirred overnight at room temperature. The solution was chilled in an ice bath and acidified with HCl (conc.) until red on pH paper. The resulting precipitate was collected by vacuum filtration, washed with water, and dried. The crude product was recrystallized from methylene chloride and hexanes to afford pure product (2.71 g, 7.54 mmol, 83percent). Mp 213?216 ¡ãC; 1H NMR (400 MHz, CDCl3, 30 ¡ãC): delta (ppm) 14.40 (s, 1H), 11.76 (s, 1H), 10.19 (s, 1H), 5.98 (s, 1H), 3.63 (q, J=6.9 Hz, 2H), 3.26 (q, J=6.9 Hz, 2H), 2.39 (q, J=7.5 Hz, 5H), 2.08 (s, 1H), 1.29 (t, J=7.5 Hz, 3H), 1.13 (t, J=7.8 Hz, 3H), 1.06 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3, 30 ¡ãC): delta (ppm) 175.8, 166.0, 142.3, 134.7, 133.1, 127.9, 127.1, 123.4, 98.5, 43.1, 39.0, 16.7, 14.3, 13.2, 13.1, 11.5, 9.52; IR (KBr) (cm?1): 1129.3, 1178.8, 1278, 1506, 1654.8, 1724.2, 2879.5, 2939, 2963.8, 3063, 3097.6, 3236.5, 3500; MS (EI+) 243, 269, 287, 315, 359 m/z; HRMS (ESI+) C19H25N3O4 calcd: 359.1845 amu; found: 359.1854 amu.

766-36-9 3-Ethyl-4-methyl-2,5-dihydro-1H-pyrrol-2-one 854146, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Jarvis, Tia; Saint-Louis, Carl Jacky; Fisch, Alexander R.; Barnes, Korry L.; Dean, Dolan; Flores, Luis A.; Hunt, Thomas F.; Munro, Lyndsay; Simmons, Tyler J.; Catalano, Vincent J.; Zhu, Lei; Schrock, Alan K.; Huggins, Michael T.; Tetrahedron; vol. 74; 14; (2018); p. 1698 – 1704;,
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

1334177-86-4, 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/i0% methanol] gave 106 as a pale yellow solid (205 mg, 72%). LC/MS: RT 5.75 mm; 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; (290 pag.)WO2016/166299; (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.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 (56 mg, 0.29 mmol, 3 eq.) was added to a stirred solution of bis-amine (9) (0.123 g, 98 IJmol, 1.0 eq.) and MaldPEGOH (0.128 g, 0.22 mmol, 2.2 eq.) in CHCb (15 ml). 15 The reaction mixture was stirred at room temperature for 30 min then diluted with CHCb (50 ml) washed with H20 (1 00 ml), saturated brine (1 00 ml), dried (MgS04) and evaporated under reduced pressure. Purification by preparative HPLC followed by lyophilisation gave the product as a white foam (0.047 g, 20%). Analytical Data: LC/MS, RT 6.61 min; MS (ES+) m/z (relative intensity) 1205 ([M + 2Ht¡¤, 55).

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

Reference£º
Patent; MEDIMMUNE LIMITED; DIMASI, Nazzareno; HOWARD, Philip Wilson; MASTERSON, Luke; TIBERGHIEN, Arnaud Charles; VIJAYAKRISHNAN, Balakumar; WHITE, Jason; (135 pag.)WO2019/34764; (2019); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

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

EXAMPLE 2 (Z)-4-methoxy-5-(cyclohexylmethylene)-3-pyrrolin-2-one (IV, R2 =H, R3 =Me, R4 =cyclohexyl) 23.9 g of 4-methoxy-3-pyrrolin-2-one (94.6 percent) in 1360 ml of 4 n sodium hydroxide solution and 27.5 g of cyclohexanecarbaldehyde (90 to 95 percent) in 330 ml of methanol were reacted as described in Example 1. Data for the product was: Yield: 39.8 g (96.1 percent) Melting point: 134¡ã to 136¡ã C., colorless crystals 1 H-NMR: delta=9.07 (br.s, 1H), 5.32 (d, 1H), 5.14 (d, 1H), 3.83 (s, 3H), 2.40 (m, 1H), 1.09-1.81 (m, 10H)

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

Reference£º
Patent; Lonza, Ltd.; US4983743; (1991); 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.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

6913-92-4, Cycloaddition of cyanonitrone 10 on 2 in order to obtain the heterobicycle 11: Cyanonitrone 10 (550 mg, 3.44 mmol) and benzyl-3-pyrroline 2 (13 ml, 6.83 mmol) are dissolved in toluene (4 ml) and stirred for 2 h at 80 C. under microwave irradiation (display temperature: 80 C.). The solvent is then evaporated before purification and separation on a silica column (eluent: AcOEt/toluene 1/10) of a regioisomer (60 mg, 6%) in order to obtain the expected racemic cycloadduct 11 (500 mg, 45%). Aspect: yellow oil. Rf=0.4 (EtOAc/toluene 1/4). 1H NMR (400 MHz, 60 C., toluene-D8): delta 7.3-7.0 (m, 10H), 4.28 (ddd, 1H, J=3.4 Hz, J=6.0 Hz, J=7.5 Hz, H-4), 4.17 (d, 1H, J=13.4 Hz, H-9), 3.81 (d, 1H, J=13.4 Hz, H-9?), 3.30 (d, 1H, J=13.1 Hz, H-8), 3.23 (d, 1H, J=13.1 Hz, H-8?), 3.06 (d, 1H, J=3.6 Hz, H-6), 2.79 (ddd, 1H, J=3.8 Hz, J=7.9 Hz, J=11.6 Hz, H-3), 2.47 (ddd, 1H, J=3.0 Hz, J=10.0 Hz, H-5), 2.24 (br m, 1H, H-5?), 2.16 (br m, 1H, H-2), 2.07 (br m, 1H, H-2?) ppm. 13C NMR (100 MHz, 60 C., toluene-D8): delta 139.3, 136.7, 129.7, 129.7, 129.0, 129.0, 128.8, 128.8, 128.8, 128.8, 128.1, 127.6, 116.5 (C-7), 81.4 C-4), 59.5 (C-8), 59.3 (3C, C-5, C-6, C-9), 57.0 (C-2), 53.0 (C-3) ppm. HRMS: m/z calcul. for C20H22N3O [M+H]+: 320.1757. found: 320.1767.

As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.

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.

To a suspension of the free thiol, 4a (88 mg, 0.105 mmol) and l-((2,5- dioxopyrrolidin-l-yl)oxy)-l-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 mu, 0.315 mmol) under nitrogen at room temperature. The mixture stirred for 16 hours and then l-(2- aminoethyl)-lH-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 (CI 8, CH3CN/H2O). Fractions containing desired product were frozen and lyophilized to give maleimide, compound D4 (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.

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

541-59-3, Maleimide is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

541-59-3, Step 1: Preparation of 3-(4-bromophenyl)-1H-pyrrole-2,5-dioneA solution of hydrochloric acid (37percent, 13 mL) in water (5.5 mL) was added to 4-bromoaniline (7.48 g, 43.52 mmol) at r.t. with vigorous stirring and the formed precipitate was allowed to stir for 30 min. The reaction mixture was cooled to 0¡ã C. and a solution of sodium nitrite (3.30 g, 47.87 mmol) in water (9 mL) was added dropwise. At the end of diazotization, a clear yellow solution was obtained. Maleimide (8.45 g, 87.05 mmol) in acetone (35 mL) was added dropwise at 0¡ã C. and then the pH of the solution was adjusted to 3-3.5 by adding sodium acetate. CuCl2 (0.88 g, 6.57 mmol) was added to the vigorously stirred mixture. The reaction mixture was stirred at 0¡ã C. for 1 h and overnight at r.t. After completion of the reaction as confirmed by TLC, solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether) to afford the title compound as a yellow solid (5.8 g, 57percent).ESIMS (m/z): 252.3 (M+1)

As the paragraph descriping shows that 541-59-3 is playing an increasingly important role.

Reference£º
Patent; PANACEA BIOTEC LTD.; US2012/165320; (2012); 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.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.

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

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, In a 50 mL round bottom flask, compound 4 (0.56 g, 2 mmol) and 3-ethyl-4-methyl-1H-pyrrol-2-one (0.275 g, 2.2 mmol) were dissolved in anhydrous ethanol (10 mL) and then DBU (1.5 mL) was added. The reaction mixture was heated at reflux for 24 h. After refluxing, the reaction mixture was cooled in an ice bath, then acetic acid (1.5 mL) was added followed by water (10 mL). The solution was chilled at?5 ¡ãC overnight, and the precipitate formed was filtered, and dried to afford the desired product (0.36 g, 1.14 mmol, 57percent). Mp 315?320 ¡ãC: 1H NMR (400 MHz, CDCl3, 30 ¡ãC) delta (ppm) 9.08 (s. 1H), 6.37 (s, 1H), 4.40 (q, J=7.20Hz, 2H), 2.76 (s, 3H), 2.45 (m, 2H), 2.15 (s, 3H), 1.43 (t, J=7. 61 Hz, 3H), 1.16 (t, J=7.61Hz, 3H); 13C NMR (100 MHz, CDCl3, 30 ¡ãC): delta (ppm) 161.7142.2, 142.1, 140.3, 137.1, 134.9, 130.1, 122.7, 117.2, 106.2, 94.1, 61.1, 16.8, 14.4, 13.1, 11.2, 9.61; IR (ATR) (cm?1): 3284 (w), 3065 (w), 2985 (w), 2870 (w), 1736 (s), 1699 (s), 1665 (w), 1453 (w), 1286 (s), 1271 (s), 1212 (m), 1106 (m), 1028 (w), 884 (w); HR-MS (EI+) C17H18N2O4 calcd: 314.1267 amu; found: 314.1445 amu.

The synthetic route of 766-36-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jarvis, Tia; Saint-Louis, Carl Jacky; Fisch, Alexander R.; Barnes, Korry L.; Dean, Dolan; Flores, Luis A.; Hunt, Thomas F.; Munro, Lyndsay; Simmons, Tyler J.; Catalano, Vincent J.; Zhu, Lei; Schrock, Alan K.; Huggins, Michael T.; Tetrahedron; vol. 74; 14; (2018); p. 1698 – 1704;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem