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

Synthesis of 1-(2-(2-azidoethoxy)ethyl)-3,4-dibromo-1H-pyrrole-2,5-dione To 2.5 g of 3,4-dibromo-1H-pyrrole-2,5-dione (10 mmol) and 1 g of NMM in 60 mL of THF, MeOCOCl (10 mmol, 940 mg in 10 ml DCM) was added dropwise, stirred for 20 min, then the reaction solution was diluted with 6o mL of DCM, washed 3 time by water, the organic phase was stirred by sodium sulfate anhydrous, concentrated, 2.65 g of methyl 3,4-dibromo-2,5-dioxo-2H-pyrrole-1(5H)-carboxylate was obtained. 311 mg, 1 mmol of this compound, 2-(2-azidoethoxy)ethanamine (130 mg, 1 mmol) and 5 mL DCM was added, TLC shown the reaction finished in 20 min, then extracted by DCM and brine, washed by NH4Cl solution, dried on sodium sulfate anhydrous, and then concentrated for column purification, flashed by 2:1 hexane and ethyl ethylate, 230 mg of 1-(2-(2-azidoethoxy)ethyl)-3,4-dibromo-1H-pyrrole-2,5-dione obtained. 1HNMR: 3.32 ppm (t, J=5.0 Hz, 1H), 3.40 ppm (t, J=5.0 Hz, 1H), 3.50 ppm (q, J=5.0 Hz, 1H), 3.62 ppm (t, J=5.0 Hz, 1H), 3.63-3.69 ppm (m, 3H), 3.84 ppm (t, J=5 hz, 1H). Fw: 365.9, C8H8Br2N4O3; Mass Peaks (1:2:1): 366.9, 368.9, 370.9.

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

Reference£º
Patent; Sorrento Therapeutics, Inc.; Fu, Yanwen; Kaufmann, Gunnar F.; Jones, Bryan; Toughiri, Rahaleh; (27 pag.)US2016/326266; (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.541-59-3,Maleimide,as a common compound, the synthetic route is as follows.

General procedure: To a solution of N-R-maleimide (10 mmol) in CCl4 (15 mL) was added dropwise a solution of Br2 (0.57 mL, 11 mmol) in CCl4 (10mL) at rt After the addition is completed, the reaction mixture was refluxed for 1 h and then cooled to room temperature. The solvent was evaporated in vacuo to give the crude trans-2,3-Dibromo-N-R-succinimide as pale-yellow solid. The crude succinimide was dissolved in THF (30 mL) and triethylamine (1.40 mL, 11 mmol) in THF (5 mL) was added dropwise at 0 oC.The resulting mixture was allowed to warm to room temperature and stirred for two h before concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine. The organic layer was dried with anhydrous Na2SO4 and evaporated in vacuo to give bromo-N-R-maleimide (1)as pale-yellow solid with good yields.

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

Reference£º
Article; Li, Xiangmin; Li, Hongxian; Yang, Wei; Zhuang, Jinchen; Li, Hao; Wang, Wei; Tetrahedron Letters; vol. 57; 24; (2016); p. 2660 – 2663;,
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.

Ac-Arg-Arg-Arg-Arg-Cys-Pro-Leu-Tyr-Ile-Ser-Tyr-Asp-Pro-Val-Cys-Arg-Arg-Arg-Arg-NH2 (2 mg) was dissolved in Dulbecco’s phosphate buffered saline (5 mL, without Ca, Mg) and acetonitrile (5 mL). 3,4-dibromomaleimide (0.2 mg, 1 eq.) was added to the solution, and the mixture was stirred for 1 h at room temperature. To the resulting mixture was added H2O (10 mL) and the solution was filtered and applied to the preparative HPLC, and linear density gradient elution (60 min) was then performed with eluents A/B: 75:25-65:35 using eluent A: 0.1% TFA in water and eluent B: 0.1% TFA-containing acetonitrile on preparative HPLC using YMC-Actus Triart Prep C8-S S-10mum 20 nm column (30 ¡Á 250 mm); flow rate: 15 mL/min. The fractions containing the product were collected and lyophilized to give 1.6 mg of peptide 15 as a yellow powder; mass spectrum: (M + H)+ 2655.54 (calcd 2655.38). Elution time on RP-HPLC: 8.05 min. Elution conditions: YMC Triart C8 column (4.6 ¡Á 100 mm), linear density gradient elution with eluents A/B = 80/20-30/70 (25 min), using 0.1% TFA in water as eluent A and 0.1% TFA-containing acetonitrile as eluent B; flow rate: 1 mL/min.

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

Reference£º
Article; Niida, Ayumu; Sasaki, Shigekazu; Yonemori, Kazuko; Sameshima, Tomoya; Yaguchi, Masahiro; Asami, Taiji; Sakamoto, Kotaro; Kamaura, Masahiro; Bioorganic and Medicinal Chemistry Letters; vol. 27; 12; (2017); p. 2757 – 2761;,
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.541-59-3,Maleimide,as a common compound, the synthetic route is as follows.

To a solution of maleimide 11 (3.0 g, 31 mmol) in ethyl acetate (120 mL) was added dropwise a solution of N-methyl morpholine (4.4 mL, 40.3 mmol) in ethyl acetate (15 mL) over 10 min at 0 oC. Then a solution of methyl chloroformate (3.1 mL, 40.3 mmol) in ethyl acetate (8.0 mL) was added dropwise, the solution was allowed to reach room temperature while stirring for 3 h. TLC showed that the starting material was consumed completely. The solution was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution, water, and saturated sodium chloride solution, successively. The organic layer was separated, dried over Na2SO4, and filtered. After the supernatant was concentrated under reduced pressure through rotary evaporation, the residue recrystallized from isopropyl ether to give compound 12 (4 g, 64.5 mmol, 84% yield) as a pale solid. 1H NMR (500 MHz, CDCl3) delta 6.89 (s, 2H), 4.01 (s, 3H); 13C NMR (126 MHz, CDCl3) delta 165.8, 148.2, 135.4, 54.4.

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

Reference£º
Article; Yue, Xuyi; Feng, Yue; Yu, Y. Bruce; Journal of Fluorine Chemistry; vol. 152; (2013); p. 173 – 181;,
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 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid 86925, apyrrolines compound, is more and more widely used in various.

Reference£º
Article; Anand, Preet; Singh, Baldev; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 521 – 530;,
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 hydrochloride (8 mg, 0.042 mmol) was added to a suspension of Maleimide-PEG8-acid (25 mg, 0.042 mmol) in dry CH2Cl2 (4 mL) under argon atmosphere. PBD 85 (42 mg, crude) was added straight away and stirring was maintained until the reaction was complete (3 hours). The reaction was diluted with CH2Cl2and the organic phase was washed with H2O and brine before being dried over MgS04, filtered and excess solvent removed by rotary evaporation under reduced pressure by rotary evaporation under reduced pressure. The product was purified by careful silica gel chromatography (slow elution starting with 100% CHCI3 up to 9:1 CHCl3/MeOH) followed by reverse phase HPLC to remove unreacted maleimide-PEG8-acid. The product 86 was isolated in 10% over two steps (6.6 mg). LC/MS 1 .16 min (ES+) m/z (relative intensity) 770.20 ([M + 2H]+ , 40%).

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

Reference£º
Patent; VAN BERKEL, Patricius Hendrikus Cornelis; HOWARD, Philip Wilson; (281 pag.)WO2016/166341; (2016); A1;; ; Patent; VAN BERKEL, Patricius Hendrikus Cornelis; HOWARD, Philip Wilson; (280 pag.)WO2016/166307; (2016); A1;; ; Patent; VAN BERKEL, Patricius Hendrikus Cornelis; HOWARD, Philip Wilson; (280 pag.)WO2016/166300; (2016); 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

250 mg (1.07 mmol) of tert-Butyl 3-[2-(2-aminoethoxy)ethoxy]propanoate, 151 mg (0.974 mmol) of 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid, 224 mg (1.46 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 224 mg (1.17 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in 5.0 ml of dimethylformamide. The reaction mixture was stirred at RT for 1 h. Ethyl acetate was added and the mixture was extracted twice with 5% strength citric acid solution and with saturated sodium bicarbonate solution. The organic phase was washed twice with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was evaporated under reduced pressure. The residue was purified by preparative RP-HPLC (column: Reprosil 250*40; 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 267 mg (64% of theory) of tert-Butyl 3-[2-(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethoxy)ethoxy]propanoate. LC-MS (Method 1): Rt=0.73 min; MS (ESIpos): m/z=371 (M+H)+.

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
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

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.

(d) 4-((2S, 5S) -37-(2, 5-dioxo-2, 5-dihydro- 1 H-pyrrol- 1 -yl) -5-isopropyl-2-methyl-4, 7, 35-trioxo- 10, 13, 16, 19, 22, 25, 28, 31 -octaoxa-3, 6, 34-triazaheptatriacontanamido)benzyl (3-(((S)-8-((5- (((S)- 7-methoxy-2-methyl-5-oxo-5, 11 a-dihydro- 1 H-benzo[e ]pyrrolo[1 , 2-a ][1 , 4 ]diazepin-8- yl)oxy)pentyl)oxy)-2-methyl-5-oxo-5, 11 a-dihydro-1 H-benzo[e]pyrrolo[1 ,2-a][1 ,4]diazepin-7- yl)oxy)propyl)carbamate (4) 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI, 15 mg, 0.080 mmol, 1.1 eq) was added to a solution of crude 3 (0.077 mmol) and Mal-(PEG)8-acid (48 mg, 0.080 mmol, 1 .1 eq) in dry dichloromethane (2 ml_). The reaction was degassed three times with Argon and stirred for 2 hours and the presence of starting material was no longer observed by LC/MS. The reaction was diluted with dichloromethane and washed sequentially with water and brine. The organic phase was dried over magnesium sulphate filtered and excess dichloromethane removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 100% chloroform to 10% methanol in chloroform). Pure fractions were collected and combined and excess eluent was removed by rotary evaporation under reduced pressure to give the desired product (40mg). This residue was then purified further by preparative HPLC (3.7 mg, 31 % over 2 steps). LC/MS 1.40 min, (ES+) m/z (relative intensity) 1521.95 [M + H]+. 1H NMR (400 MHz, CDCI3) delta 8.72 (s, 1 H), 7.83 (s, 1 H), 7.80 (d, J = 3.9 Hz, 1 H), 7.63 – 7.61 (m, 2H), 7.47 (d, J = 8.3 Hz, 2H), 7.26 (br, 2H), 6.77 – 6.75 (m, 4H), 6.69 (s, 2H), 5.02 (s, 2H), 4.64 – 4.62 (m, 2H), 4.24 – 4.21 (m, 4H), 4.19 – 3.95 (m, 4H), 3.89 (s, 2H), 3.86 – 3.75 (m, 4H), 3.63 (br, 32H), 3.53 – 3.33 (m, 8H), 3.18 – 3.14 (m, 2H), 2.98 – 2.94 (m, 2H), 2.53 – 5.49 (m, 3H), 2.03 (s, 2H), 1.83 (br, 10H), 1 .56 (br, 2H), 1.42 (s, 3H), 1.05 – 0.90 (m, 6H).

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

Reference£º
Patent; MEDIMMUNE LIMITED; HOWARD, Philip, Wilson; (203 pag.)WO2016/37644; (2016); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

7544-75-4, 3,4-Dihydro-2H-pyrrol-5-amine hydrochloride is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1) A DMA (35 ml) suspension containing Compound 1 (5.57 g, 28 mmol), Compound 2 (10 g, 83 mmol) and sodium carbonate (12 g, 113 mmol) was stirred at 80 C. for 15 hours under argon atmosphere. After cooling by allowing to stand, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:2) to give Compound 3 (2.02 g, 11 mmol, 39%) as a solid.

As the paragraph descriping shows that 7544-75-4 is playing an increasingly important role.

Reference£º
Patent; Kusama, Mari; Watanabe, Tatsuya; Hosaka, Toshihiro; Kubota, Yuko; US2008/9506; (2008); 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

(0435) To a solution of the NHS ester, 2b (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 (C18 column, CH3CN/H2O). The fractions that contained pure product were combined, frozen and lyophilized to give the desired maleimide, compound D2 (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.; Hilderbrand, Scott A.; Hutchins, Benjamin M.; (94 pag.)US2018/208562; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem