Heterocyclic Building Blocks-Pyrrolines

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

511 mg (1.95 mmol) of triphenylphosphine was dissolved in 5 mL of anhydrous THF and stirred.0.38 mL (1.95 mmol) of azoxylene diisopropyl ester was added dropwise to the above solution, and stirred at -78 C for 5 min.After 0.25 mL (1.56 mmol) of triethylene glycol monomethyl ether was dissolved in 5 mL of anhydrous THF, the reaction mixture was added dropwise to the azoazolyl diisopropyl ester solution, and stirring was continued at -78 C for 5 min.Thereafter, neopentyl alcohol 121 mg (1.37 mmol) was dissolved in 2 mL of anhydrous THF, added to triethylene glycol monomethyl ether, and stirred at -78 C for 5 min.Finally, 497 mg (1.95 mmol) of dibromomaleimide was added to the above reaction solution, stirred at -78 C for 10 min, then transferred to room temperature, and magnetically stirred at room temperature for 20 h.The crude product was purified by column chromatography (volume ratio EA_PA=1:10-1:4), and then isolated by medium pressure to obtain the white target product, intermediate 1 325 mg, yield 52.2%.

1122-10-7, 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; Henan Normal University; Jiang Tao; Wang Zhiying; Wang Jie; Chi Yanwei; Dong Wenpei; Zhang Yue; Xin Pengyang; Chen Changpo; (11 pag.)CN109293683; (2019); 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

A cooled suspension (0 C) of molecule 3 (211 mg, 0.97 mmol) in methylene chloride (4.5 mL) was treated with triethylamine (190 mu, 1.36 mmol) and isobutyl chloroformate (175 mu, 1.34 mmol). The mixture was stirrred for 1 h at 0C 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 22C. The reaction mixture was diluted with ethyl acetate (55 mL) and methylene chloride (20 mL) and washed twice with saturated NaHC03(2 x 50 mL), twice with 0.1 N HCl (2 x 50 mL), twice with saturated NaCl (2 x 50 mL), and finally with H20 (50 mL). The organic phase was dried (MgS04) and evaporated to give crude derivative 4. The product was purified by flash chromatography, using a mixture of hexanes / acetone (3/2), to yield 173 mg (54%) of 4. The spectral data of this derivative correspond to those reported in the literature.10IR (v, cm”1): 3360-3240 (NH), 3087 (C=C), 2988 (CH, aliphatic), 1733 (C=0), 1706 (C=0); 1H NMR (acetone-d6, delta ppm): 9.05 (s, 1H, NH), 8.02 and 7.53 (2 x d, J=8.6 Hz, 4H, aromatic), 7.07 (s, 2H, maleimide), 2.84 (br s, 1H, NH), 1.45 (s, 9H, 3 x CH3);13C NMR (acetone-d6, delta ppm): 169.3 (2), 166.0, 155.7, 135.1, 134.6 (2), 131.6, 127.9 (2), 125.9 (2), 79.6, 27.5 (3); ESI+HRMS: (M+Na)+ calculated for C16H17N3NaO5 = 354.1060; found = 354.1072; (M -2-methylpropene +H)+ calculated for C12H11N3O5= 276.0620; found = 276.0627., 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
Patent; 3R VALO, S.E.C.; BERUBE, Gervais; REYES-MORENO, Carlos; (121 pag.)WO2017/177316; (2017); A1;,
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

To a solution of the NHS ester, 6b (12.3 mg, 0.011 mmol) and N-(2- aminoethyl)maleimide hydrochloride (2.0 mg, 0.011 mmol) in anhydrous dichloromethane (0.3 mL) was added DIPEA (0.0022 mL, 0.013 mmol). The mixture was stirred at room temperature for 3 hours then it was stripped under reduced pressure. The residue was purified by semi-preparative reverse phase HPLC (CI 8 column, CH3CN/H2O). The fractions that contained pure product were combined, frozen and lyophilized to give the desired maleimide, compound D6 (10 mg, 80% yield). LCMS = 8.3 min (15 min method). MS (m/z): 1181.8 (M + D+)., 134272-64-3

As the paragraph descriping shows that 134272-64-3 is playing an increasingly important role.

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

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/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.

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

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

First of all, 2-(trimethylsilyl)ethyl N6-(tert-butoxycarbonyl)-L-lysinate was prepared proceeding from N2-[(benzyloxy)carbonyl]-N6-(tert-butoxycarbonyl)-L-lysine by conventional methods of peptide chemistry. This intermediate was then coupled in the presence of HATU and N,N-diisopropylethylamine with the tripeptide unit N-[(benzyloxy) carbonyl]-L-valyl-L-alanyl-beta-alanine prepared by standard methods. The Z protecting group was then removed by hydrogenolysis in methanol and the intermediate obtained was coupled to (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N diisopropylethylamine. In the last step, the side-chain amino group was deprotected under gentle conditions by stirring in 10% trifluoroacetic acid in DMF at RT for 1 h. After concentration and freeze-drying from acetonitrile/water, the title compound was obtained. LC-MS (Method 1): Rt=0.64 min; MS (ESIpos): m/z=625 (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; 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

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

Piperidine (0.2 mL) was added to a solution of 25 (77 mg, 63.4 pmol) in DMF (1 mL). The reaction mixture was allowed to stir for 20 minutes. The reaction mixture was carefullydiluted with DCM (50 mL) and washed with water (50 mL). The organic layers was washed with brine (100 mL), dried over Mg504, 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 pmol) and EDCI (18 mg, 95 pmol) 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 mm (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 (MgSO4), 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 CHCI3/MeOH to 90:10 v/v CHCI3/MeOH) gave 26 as a yellow solid (43 mg, 43%). 1H NMR (400 MHz, CDCI3)58.73 (s, IH), 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, I 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, I H), 4.72 – 4.63 (m, I 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, I H), 2.59 (s, 4H), 2.55 – 2.43 (m, 3H), 2.37 (s, 3H), 2.29 (dd, J = 12.7, 6.7Hz, IH), 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 = 11 .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; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius, Hendrikus, Cornelis; WO2015/52535; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

55750-49-7, Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

55750-49-7, a) N-(tert.-butyloxycarbonyl)-2-(N-maleinimido)ethylamine 0.8 g (5 mmol) of the compound produced according to Example 1a is dissolved in 25 ml saturated sodium bicarbonate solution. The solution is filtered over a folded filter and cooled to 0 C. Subsequently 0.84 g (5 mmol) N-(ethoxycarbonyl)maleinimide (produced according to the method of O. Keller and J. Rudinger, Helv. Chim. Acta 58 (1975), 531-541) is added while stirring and it is left to stir for a further 15 min at room temperature. During this the N-(ethoxycarbonyl)maleinimide dissolves completely after a short time while the title compound precipitates during the course of the reaction. 40 ml THF is added and stirred for a further 45 min at room temperature. Afterwards it is adjusted to pH 6.0 with 1n HCl, extracted twice with 50 ml acetic ester and the extract is dried with 5 g Na2 SO4. After evaporation in a water-jet vacuum the title compound is obtained as a colourless, solid residue. Yield: 1.1 g (92% of the theoretical yield). TLC: silica gel, chloroform/acetic ester (66/33 v/v), spray with 0.1% KMnO4 solution; Rf =0.50.

As the paragraph descriping shows that 55750-49-7 is playing an increasingly important role.

Reference£º
Patent; Boehringer Mannheim GmbH; US5595741; (1997); 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.63468-63-3,2,5-Dihydro-1H-pyrrole hydrochloride,as a common compound, the synthetic route is as follows.

63468-63-3, To a solution of 2,5-dihydro-lH-pyrrole hydrochloride (12 g, 0.11 mol) in H2O (100 niL) was added EtOAc (100 niL) and K2CO3 (89 g, 0.64 mol). The mixture was stirred at RT for 30 min. Cbz-Cl (22 g, 0.13 mol) was added dropwise at 0C and the mixture was stirred for 1 h. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4. The solvent was removed in vacuo to afford the crude product (25 g, 95%), as a light oil, which was carried directly to the next step.

As the paragraph descriping shows that 63468-63-3 is playing an increasingly important role.

Reference£º
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); 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

Reference Example 18 Preparation of 3,4-Bis-(2-hydroxy-ethylsulfanyl)-pyrrole-2,5-dione To 2-mercaptoethanol (683.8 mul, 9.8 mmol) in buffer (100 ml, 150 mM NaCl, 100 mM sodium phosphate, pH 8.0, 5.0% DMF) was added di-bromomaleimide (1 g, 3.9 mmol) in DMF (2.5 ml, final concentration DMF 7.5%). The reaction was stirred for 30 min at RT and lithium chloride (20 g) was added. The aqueous reaction mixture was extracted with ethyl acetate (7*150 ml). The organic layers were combined, the solvent removed in vacuo and the residual material was purified by flash chromatography on silica gel (petroleum ether:ethyl acetate, gradient elution from 1:1 to 1:9). Fractions containing the product were collected and the solvent were removed in vacuo. The still impure product was purified by flash chromatography on silica gel (methanol:dichloromethane, gradient elution from 0.5-10.0% methanol) to afford the desired compound as a yellow solid (518 mg, 53%). lambdamax (50 mM sodium phosphate, pH 6.2, 40% MeCN, 2.5% DMF)/318 nm (epsilon/dm3 mol-1 cm-1 1855); 1H NMR (500 MHz, MeOD): delta=3.74 (t, 4H, J=6.4, 2*HO-CH2), 3.41 (t, 4H, J=6.3, 2*S-CH2) 13C NMR (125 MHz, MeOD): delta=168.5 (C), 137.2 (C), 62.3 (CH2), 34.4 (CH2); IR (solid, cm-1): 3344 (s), 2500 (m), 2078 (w); MS (EI) m/z, (%): 250 (M, 43), 232 (100), 161 (37); Mass calc. for C8H11O4NS2: 250.02077. Found: 250.02126; m.p. 46-50 C.

1122-10-7, 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

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 32 (92 mg, 0.1 mmol, 1.1 equiv.) was dissolved in CHC13 (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 wasleft 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 (CHC13 with 1% to 10% MeOH gradient) yielding 33 (8 1mg). The material was purified further by preparative HPLC to give 33 as a yellow solid (26.3 mg, 18%). Fast Formic run: LC/MS (1.39 mm(ES+) mlz (relative intensity) 1485.00 ([M + H]+., 64)., 1334177-86-4

The synthetic route of 1334177-86-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; STEM CENTRX, INC.; SPIROGEN SARL; TORGOV, Michael; HOWARD, Philip Wilson; WO2014/130879; (2014); A2;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem