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.

Dibromomaleimide 1a, 2.0 g (7.84 mmol), was dissolved in 15 mL of anhydrous DMF, and 0.9 mL (9.51 mmol) of 4-fluoroaniline and 2 mL (11.5 mmol) of DIPEA were added. The mixture was stirred for 24 h at 50C and poured into a mixture of water and ethyl acetate. The organic layer was separated, washed with dilute aqueous HCl, and evaporated under reduced pressure, and the residue was purified by column chromatography using petroleum ether-ethyl acetate (5 : 1) as eluent. Yield 503 mg (22%), pale yellow crystals, mp 208-210C; HPLC: tau = 11.09 min, 96%. 1H NMR spectrum, delta, ppm: 7.15-7.23 m (4H), 9.60 s (1H, 4-NH), 10.96 s (1H, N1H). 13C NMR spectrum, deltaC, ppm: 80.39, 114.83 d (J = 22.8 Hz), 126.64 d (J = 8.5 Hz), 132.89, 141.73, 159.63 d (J = 242.0 Hz), 167.04, 168.4. Mass spectrum: m/z 284.9703 [M + H]+. C10H6BrFN2O2. Calculated: M + H 284.9669.

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

Reference£º
Article; Panov; Simonov, A. Yu.; Korolev; Russian Journal of Organic Chemistry; vol. 55; 12; (2019); p. 1847 – 1852; Zh. Org. Khim.; vol. 55; 12; (2019); p. 1850 – 1856,7;,
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.541-59-3,Maleimide,as a common compound, the synthetic route is as follows.

541-59-3, Preparation 1: 3-(4-bromophenyl)-1H-pyrrole-2,5-dione (P1) A solution of hydrochloric acid (37percent, 27 ml.) in water (11 ml_) was added to 4-bromo aniline (15 g) at room temperature with vigorous stirring and the formed precipitate was allowed to stir for further 30 minutes. Temperature was reduced to 0 0C and a solution of sodium nitrite (6.60 g) in water (17 ml_) was added dropwise to the stirred suspension. At the end of diazotisation, a clear yellow solution was obtained. Maleimide (16.90 g) in acetone (70 mL) was added dropwise at 0 0C and then the pH of the solution was adjusted to 3-3.5 by adding sodium acetate. Copper (II) chloride (1.76 g) was added to the vigorously stirred mixture. The reaction mixture was allowed to stir at 0 0C for 1 h and overnight at room temperature. Acetone was removed in vacuo, the residue was filtered and dried overnight in vacuo to give the crude title compound (14.12 g) which was used without further purification.MS (mlz): 251 [M-H]”.

The synthetic route of 541-59-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/22935; (2007); 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.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 DBM (3.00 g, 11.7 mmol) and NMM (1.30 mL,11.7 mmol) in THF (135 mL), MCF (0.90 mL, 11.7 mmol) was added and the mixture was stirred for 1 h at room temperature. The solvent was removed in vacuo, and then DCM (100 mL) was added. The organic phase was sequentially washed with water and brine, and then dried over anhydrous MgSO4. After filtration, the solvent was removed in vacuo to generate the intermediate 1 as a pink powder in quantitative yield. The compound 1 was directly subjected to the next synthetic step without further purification., 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
Article; Li, Zi-Long; Sun, Linhao; Ma, Jimei; Zeng, Zhen; Jiang, Hong; Polymer; vol. 84; (2016); p. 336 – 342;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

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

6913-92-4, Was synthesised according to published methods:. To a solution of 1-benzyl-3-pyrroline (5.0 g, 31.40 mmol) in methanol (20 ml) cooled at 0C, water was added (5 ml) and H2S04 96% (2 ml). The solution was stirred 5 min. and 3-chloroperoxybenzoic acid (10.0 g, 40.56 mmol) was added in portions. The suspension was stirred at r.t. for 18 h. Methanol was evaporated and the aquose solution was neutralized with aq. NaOH 10 % until pH=7. The suspension was extracted with dichloromethane and the organic phase was washed with water and saturated solution of NaCl, dried over Na2SO4, filtered and concentrated to afford pure product (4.35 g, 80%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.49-7.23 (m, 5H), 3.81 (s, 2H), 3.66 (s, 2H), 3.23 (d, J=12Hz, 2H), 2.72 (d, J=12Hz, 2H).

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

Reference£º
Patent; Laboratorios del Dr. Esteve S.A.; EP1849781; (2007); 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

151038-94-7, The synthesis of DOXO-EMCH was accomplished using the procedure reported by Willner et al, with several changes to improve the yield (Willner, D., et al.,Bioconjugate Chem., 4:521-27, 1993). DOX’HCl (20 mg, 34 muiotaetaomicron) was dissolved in 6 mL of methanol. Pyridine (12.53 mu) was added to the solution, followed by 35.4 mgEMCH’TFA. The reaction was stirred at room temperature overnight. By HPLC, the reaction was 90% complete. The solvent was evaporated to dryness by rotary evaporation. A minimal amount of methanol was used to dissolve the solid, and six volumes of acetonitrile at 4 C were added to the solution. The resulting solution was allowed to sit undisturbed at 4 C for 48 h for crystallization. The precipitate was collected, and the crystallization method was repeated 4 times. The resulting solids were combined and washed three times with 1 : 10 methanokacetonitrile. The final yield of DOXO-EMCH was 11.59 mg, 58%. HPLC Method 1.1 was used. NMR spectra corresponded to those previously given by Willner (Bioconjugate Chem. 4:521-27. 1993).

As the paragraph descriping shows that 151038-94-7 is playing an increasingly important role.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; KOCH, Tad, H.; BARTHEL, Benjamin, L.; ROWAN, Alexander, R.H.; WO2012/167255; (2012); A1;,
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.69778-83-2,4-Methoxy-1H-pyrrol-2(5H)-one,as a common compound, the synthetic route is as follows.,69778-83-2

A. A solution of 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran (15 g) and 4-methoxy-3-pyrrolin-2-one (8.5 g) in dimethylsufoxide (40 ml) was stirred and sodium hydride (80percent dispersion in oil, 2.2 g) was added. The mixture was stirred at room temperature for 5 hours. Water (50 ml) was slowly added, and the resulting solution extracted with ethyl acetate (2*50 ml). After drying the organic layer with sodium sulfate the solvent was removed under reduced pressure and the residual oil chromatographed on silica gel (4percent methanol in methylene chloride). The product obtained was dissolved in diethylether and precipitated with pentane to afford 4 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-methoxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran, m.p. 256¡ã C.

69778-83-2 4-Methoxy-1H-pyrrol-2(5H)-one 574769, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; Researche Syntex France, S.A.; US4997846; (1991); A;,
Pyrroline – Wikipedia
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73286-71-2,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.

Anhydrous toluene (150 ml), N-Boc 2-pyrroline (1.5 g; 8.9 mmol) and anhydrous lithium fluoride (23 mg; 0.88 mmol) were mixed under argon, and the mixture was heated to reflux. After 30 min TFDA (3.88 g; 15.5 mmol) in toluene solution (10 ml mixture volume) was added by 1 ml portions to the reaction mixture over 140 min, while reflux was continued. The reaction mixture was refluxed for additional 5 h. The solvent was removed under reduced pressure and resulting crude material was purified on a silica gel column using hexane-ethyl acetate 2:1 mixture as an eluent (Rf = 0.4). 1.01 g of the product was obtained as orange oil (yield 52%). 1H NMR (CDCl3, 500 MHz), Boc-rotamers (ratio 3:2): 3.86 and 3.71 (two br m, 1H, N-CH) 3.68 (br m, 1H, N-CHH), 3.28 and 3.15 (two br m, 1H, N-CHH), 2.19 (m, 3H, CH-CH2), 1.45 (s, 9H, CH3). 13C NMR (CDCl3, 126 MHz), Boc-rotamers: 154.3 (s, C=O), 111.9 (dd, J = 293 and 302 Hz, CF2), 80.0 (s, CMe3), 46.6 (br s, major) and 46.0 (br s, minor, N-CH2), 41.4 (dd, J = 11 and 15 Hz, N-CH), 27.9 (s, CH3), 26.7 (m, major) and 25.3 (m, minor, CH), 22.9 (s, minor) and 22.2 (s, major, CH2). 19F NMR (CDCl3, 376 MHz), Boc-rotamers: -128.9 (dd, JF-F = 161, JF-H = 11 Hz, major) and -129.3 (dm, JF-F = 160 Hz, minor, exo-F), -153.9 (d, JF-F = 160 Hz, minor) and -154.4 (d, JF-F = 161 Hz, major, endo-F). IR: 3076, 2974, 1683. Mass-spectrum (m/z): 200, 164 [M-tBu+1]. CHN (found/calc.): 54.40/54.79 C, 6.86/6.90 H, 6.42/6.39 N.

The synthetic route of 73286-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Kubyshkin, Vladimir; Kheylik, Yurii; Mykhailiuk, Pavel K.; Journal of Fluorine Chemistry; vol. 175; (2015); p. 73 – 83;,
Pyrroline – Wikipedia
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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

(DM 1 -GMB- Ala-Gly-Gly)2-Lys-b-Ala-OH (5.3 mg, 0.0022 mmol) was dissolved in anhydrous dimethylformamide (0.25 mL) to which was added EDC (2.0 mg, 0.014 mmol). After 2 min 2-amino-ethyl-maleimide HC1 salt (1 mg, 0.0057 mmol) was added and the solution was stirred at room temperature for 15 min. The reaction mixture was purified by HPLC on a XB-C18 21.2×150 mm, 5muiotaeta column with a flow rate of 21.2mL/min. eluting with deionized water containing 0.1% formic acid using a gradient of acetonitrile 5% for 4 min then a linear gradient of 5% – 95% over 17 min. Fractions containing desired product were combined, frozen and lyophilized to give 2 mg (35 % yield) of white solid. MS [M + Na]+ calcd. 2537.0; found 2537.3.

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

Reference£º
Patent; IMMUNOGEN, INC.; WIDDISON, Wayne, C.; CHARI, Ravi, V.J.; WO2014/194030; (2014); A2;,
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1-Pyrroline | C4H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17057-04-4,4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid,as a common compound, the synthetic route is as follows.

General procedure: An oven-dried flask was cooled under a stream of nitrogen and charged with azomethine N-oxide 1 (5 mmol), maleimide 2 (5 mmol) and sodium dried toluene (25 mL). The flask was equipped with a reflux condenser and the mixture was refluxed for 6 hrs (Scheme 3) until the substrates were consumed as judged by TLC. On completion the reaction mixture was concentrated and the precipitated compound was filtered. The crude product consists of a mixture of cis and trans isomers which was subjected to column chromatography over silica gel (100-200 mesh) using hexane: ethyl acetate (9:1) mixture as eluent., 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
Article; Kaur, Anjandeep; Singh, Baldev; Jaggi, Amteshwar Singh; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 797 – 801;,
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.

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

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

Reference£º
Patent; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius Hendrikus Cornelis; WO2015/52533; (2015); A1;; ; Patent; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius Hendrikus Cornelis; WO2015/52534; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem