Heterocyclic Building Blocks-Pyrrolines

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 a solution of 3,4-dibromomaleimide (1.00g, 3.9mmol) and N-methylmorpholine (0.43ml_, 3.90mmol) in THF (50ml_), methylchloroformate (0.30ml_, 3.90mmol) was added and the mixture was stirred for 20minutes at room temperature. To this mixture, dichloromethane (DCM, 40ml_) was added and the organic phase was washed with water (3x100ml_), dried with MgS04. The solvent was removed in vacuo to yield the titled product as a purple powder. 1H NMR (CDCIs, 300MHz) d (ppm): 4.01 (3H, s, COCH3). 13C NMR(CDCI3, 75MHz) d (ppm): 131 .4(C=C), 54.8 (COCH3).

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

Reference£º
Patent; UNILEVER PLC; UNILEVER N.V.; CONOPCO, INC., D/B/A UNILEVER; KHOSHDEL, Ezat; BATES, Susan; HAND, Rachel, Alice; HADDLETON, David, Mark; KIRBY, Gavin, William; (20 pag.)WO2019/201787; (2019); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

766-36-9, 3-Ethyl-4-methyl-2,5-dihydro-1H-pyrrol-2-one is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 12kg of toluene to the 50L glass reactor.5.0 kg of compound A, 7.06 kg of compound B; start stirring and heating,The temperature was raised to 120-130 ¡ã C for refluxing for 2 hours; the sample was sent to HPLC for control;At the end of the reaction, cool down to 20-25 ¡ã C,Filtration; the filter cake was vacuum dried to obtain 9.25 kg of solid intermediate 1,The HPLC purity was >99percent and the molar yield was 85percent.The filtrate is directly applied to the next batch of addition I reaction.Repeat the above operation,10.33 kg of Intermediate 1 was obtained with HPLC purity >99percent and molar yield of 97percent.

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
Patent; Jiangxi Learned Xinhe Pharmaceutical Co., Ltd.; Xie Xiping; Leng Zhi; Liu Yi; Yin Qinghua; Zhang Zuofang; Ye Gang; (13 pag.)CN108383768; (2018); A;,
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 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; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius Hendrikus Cornelis; WO2015/52532; (2015); 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

Example 2 Synthesis of 39-(3,4-dibromo-2,5-dioxopyrrolyl)-3,6,9,12,15,18,21,24,27,30,33,36-dodecaoxanonatriacontanoic acid A 100 mL two-necked round bottom flask was flame dried and cooled under nitrogen. The cooled flask was charged with 200 mg (0.296 mmol) of tert-butyl 39-hydroxy-3,6,9,12,15,18,21,24,27,30,33,36-dodecaoxanonatriacontanoate. Triphenylphosphine, 106 mg, was dissolved in about 5 mL anhydrous tetrahydrofuran in a vial, and the solution was added to the 100 mL flask via cannula under nitrogen. The 100 mL flask was cooled in an ice-water bath for 15 minutes. To the cooled solution was added 55 mg (0.217 mmol) 3,4-dibromopyrrole-2,5-dione with stirring until a clear solution was observed. DIAD, 58.3 muL, was added to the cooled reaction mixture, which was stirred in the ice bath for an additional 10 minutes. The reaction mixture was stirred and allowed to reach room temperature over about 20 hours, then concentrated on a rotary evaporator until dry, giving a yellow viscous oil, which was absorbed onto about 1 g silica gel and dry-loaded onto a Reveleris normal phase chromatography unit. The oil was eluted over a 12 g silica gel cartridge with a methanol:dichloromethane gradient from 1:0 to 9:1 over 28 column volumes. The fractions containing the desired product were pooled and concentrated to dryness. The purified product was suspended in 50:50 acetonitrile:water and lyophilized overnight to provide a clear light yellow viscous oil.

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

Reference£º
Patent; Igenica Biotherapeutics, Inc.; Jackson, David Y.; Ha, Edward; Probst, Gary D.; US2014/363454; (2014); 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

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)+.

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.73286-71-2,N-Boc-2-pyrroline,as a common compound, the synthetic route is as follows.

N-Boc pyrroline (270 mg; 1.60 mmol), chloro oxime 2f (470 mg; 3.00 mmol) and sodium bicarbonate (760 mg; 9.04 mmol) in isopropanol (10 mL) were heated at 40 C. overnight. An additional portion of chloro oxime and sodium bicarbonate was added and heating continued for 20 hours. After cooling, the volatiles were evaporated. The residue was dissolved in ethyl acetate (50 mL), and washed with water (50 mL). The organic layer was dried (MgSO4), filtered and evaporated. Cycloadduct 3f was isolated as a beige powder after chromatography with 70% ethyl acetate/hexanes.MS 290 (M+H).

73286-71-2 N-Boc-2-pyrroline 10844857, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; Macielag, Mark J.; Weidner-Wells, Michele A.; Lin, Shu-Chen; US2009/29980; (2009); 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 (56 mg, 0.29 mmol) was added to a stirred solution of MAL-dPEG8-acid (172 mg,0.29 mmol, Stratech Scientific Limited) and the amine 110 (261 mg, 0.26 mmol) in dry DCM(10 mL) at room temperature. The reaction mixture was stirred under an argon atmospherefor 2.5 hours at which point analysis by LC/MS showed complete conversion to desiredproduct at retention time 1 .38 minutes, ES+ mlz 1585 [M+ Na], 1563 [M+ H].Thereaction mixture was diluted with DCM (30 mL) and washed with H20 (20 mL), brine (2 x20 mL), dried (Mg504), filtered and evaporated in vacuo to provide the crude product. Purification by lsoleraTM (DCM/MeOH, SNAP Ultra 25 g, 75 mL per minute) gave the amideIll (eluting at 91% DCM/MeOH) as a white foam (277 mg, 67% yield).

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; MEDIMMUNE LIMITED; HOWARD, Philip Wilson; GREGSON, Stephen John; (207 pag.)WO2018/192944; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

151038-94-7, 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of acetate 4-(l-(2-(6-(2,5-dioxo-2H-pyrrol-l(5H)- l)hexanoyl)hydrazono)ethyl) phenyl carbamate oxaliplatin: Acetoxyoxalplatin(4- acetylphenyl)carbamate (228 mg, 0.36 mmol, 1.00 equiv.) was dissolved in DMF (0.05 M, 7 mL) and treated with 6-(2,5-dioxo-2,5-dihydro-lH-pyrrol-l-yl)hexanehydrazide TFA salt (158 mg, 0.47 mmol, 1.30 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was triturated with acetonitrile to precipitate the product as a yellow powder. This powder was triturated first with isopropyl alcohol (iPrOH) and then with DCM to afford the desired product (70 mg, 23%, 93.5% pure). HPLC-MS 93.5%, m/z for C29H38N60iiPt [(M+H)+] = 842.3. NMR (500 MHz, DMF-dv) delta 10.34-10.15 (m, 1H), 9.91-9.66 (m, 1H), 9.37- 9.24 (m, 1H), 8.88-8.66 (m, 2H), 8.59-8.48 (m, 1H), 7.80-7.73 (m, 2H), 7.61-7.53 (m, 2H), 7.04-6.98 (m, 2H), 3.50-3.43 (m, 2H), 3.14-3.02 (m, 1H), 2.75-2.70 (m, 1H), 2.43- 2.25 (m, 6H), 2.01-1.92 (m, 3H), 1.74-1.53 (m, 9H), 1.42-1.24 (m, 4H).

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; PLACON THERAPEUTICS, INC.; KADIYALA, Sudhakar; MOREAU, Benoit; BILODEAU, Mark T.; WHALEN, Kerry; SINGH, Sukhjeet; WOOSTER, Richard; LEMELIN, Charles-Andre; (151 pag.)WO2016/209935; (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.134272-64-3,N-(2-Aminoethyl)maleimide Hydrochloride,as a common compound, the synthetic route is as follows.

Step 2: To a solution of the NHS ester, compound 6a (12.3 mg, 0.011 mmol) and N-(2- aminoethyl)maleimide hydrochloride (2.0 mg, 0.011 mmol) in anhydrous dichloromethane (0.3 niL) was added DIPEA (0.0022 niL, 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 + 1)+.

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

Reference£º
Patent; IMMUNOGEN, INC.; KOVTUN, Yelena; TAVARES, Daniel; RUI, Lingyun; CHITTENDEN, Thomas; (386 pag.)WO2017/4026; (2017); 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

To a stirred solution of 2,3-dibromomaleimide (510 mg, 2.0 mmol) in CH2Cl2 (20 mL) Et3N(277 ml, 2.0 mmol) was added, then cooled to 0 C and n-propylmercaptan(186 ml, 2.0 mmol) dissolved in CH2Cl2 (10 mL) wasadded dropwise under an argon atmosphere and stirred for 5 h. Thereaction mixture was concentrated, and the crude product waspurified by flash chromatography (hexanes:ethyl acetate 9:1) togive the desired intermediate (261 mg, 52%) as a yellow powder. Toa stirred solution of the intermediate (261 mg,1.04 mmol) in CH2Cl2(20 mL) Et3N (160ml, 1.1 mmol) and n-dodecyl-mercaptan (264 ml,1.1 mmol) were added under an argon atmosphere and stirred for30 min. The reaction mixture was concentrated, and the crudeproduct was purified by flash chromatography (hexanes:ethyl acetate 95:5) to give compound 9a (273 mg, 71%) as a yellowpowder. 1H NMR (400 MHz, CDCl3): d 7.60 (s, 1H, NH), 3.34e3.22(m, 4H, 2x S-CH2), 1.74e1.59 (m, 4H), 1.45e1.37 (m, 2H), 1.30e1.21(m, 16H), 1.03 (t, J 7.4 Hz, 3H), 0.88 (t, J 6.8 Hz, 3H). 13C NMR(101 MHz, CDCl3): d 166.61, 166.40, (2C, 2 x CO) 136.98, 136.71,(2C, 2 x C-S) 33.79, 32.04, 31.95, 30.59, 29.76, 29.69, 29.60, 29.48,29.24, 28.62, 24.03, 22.82, (13C, 13 x CH2) 14.26, 13.23. (2C, 2 x CH3).MS (MALDI-TOF): m/z calculated for C19H33NO2S2 Na [M Na]:394.18. Found: 394.25. Compound 9a was converted into Nethoxycarbonylcompound according to general method A. Thecrude compound 9bwas used in further steps without purification.

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; Sz?cs, Zsolt; Kelemen, Viktor; Le Thai, Son; Csavas, Magdolna; R?th, Erzsebet; Batta, Gyula; Stevaert, Annelies; Vanderlinden, Evelien; Naesens, Lieve; Herczegh, Pal; Borbas, Aniko; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1017 – 1030;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem