Category: pyrrolines

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.

General procedure: Acyl chloride (1.2 mmol, 1.2 equiv) was added to a solution of 4-dimethylaminopyridine (DMAP) (1.2 mmol, 1.2 equiv) in acetonitrile (1.0 mL) at 0 ¡ãC. The reaction was stirred at room temperature for 15 min. A solution of the 5-methyl-3,4-dihydro-2H-pyrrole (1.0 mmol) in acetonitrile (1.0 mL) was added and the reaction was stirred at room temperature for 3 h. p-Toluenesulfonic acid monohydrate (3.0 mmol, 3.0 equiv) was added at 0 ¡ãC under inert atmosphere. The reaction was then stirred at room temperature for 2 h. Arylhydrazine (1.5 mmol, 1.5 equiv) was added and stirred for an addition 5 min at room temperature. The reaction was then heated to 82 ¡ãC for 20 h. The reaction cools down to room temperature. The residue was then dissolved in ethyl acetate and washed with brine and a saturated aqueous solution of NaHCO3. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude solid, which was purified by column chromatography on silica gel., 872-32-2

872-32-2 2-Methyl-1-pyrroline 70103, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Article; Yeo, Se Jeong; Liu, Yongxiang; Wang, Xiang; Tetrahedron; vol. 68; 3; (2012); p. 813 – 818;,
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.31970-04-4,Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

Example 1.3: Benzyl 3,4-epoxypyrrolidine-i-carboxylate (5); NBS (5.47 g, 31 mmol) is added to a solution of olefin 4 (5.02 g, 25 mmol) in DMSO (65 mL) and water (3.4 mL) at 0 0C. The reaction mixture is warmed to room temperature, stirred for 1.5 h then further NBS (1.1 g, 6.2 mmol) is added. After stirring for a further 3.5 h the reaction is quenched by the addition of water (150 mL) then extracted into EtOAc (3 x 150 mL). The combined organic phase is washed with brine (3 x 100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue is dissolved in MeOH (80 mL), cooled to 0 0C and then an aqueous solution of NaOH (37 mL, 37 mmol, 1 M) is added in one portion. The reaction is warmed to room temperature, stirred for 5 h then the MeOH is removed under reduced pressure. The residue is diluted with water (100 mL) and extracted into EtOAc (3 x 200 mL). The combined organic phase is washed with brine (200 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Flash chromatography of the residue (3 : 7 then 4 : 6, EtOAc: Petrol) affords the title compound as a pale yellow oil (3.69 g, 68% over the 2 steps). 13C NMR (125 MHz, CDCI3): delta = 155.3, 136.6, 128.5, 128.0, 127.9, 67.0, 55.5, 54.9, 47.5 and 47.2 ppm; MS (ESI): 242 ([MNa]+, 100%); HRMS (ESI): found: 242.0791 , C12H13NO3Na ([MNa]+) requires: 242.0793. (Tetrahedron: Asymmetry, 2006, 17, 2876-2883).

31970-04-4, 31970-04-4 Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate 643471, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; ALBERT EINSTEIN COLLEGE OF YESHIVA UNIVERSITY; INDUSTRIAL RESEARCH LIMITED; EVANS, Gary Brian; LONGSHAW, Alistair Ian; SCHRAMM, Vern L.; TYLER, Peter, Charles; WO2011/8110; (2011); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

872-32-2, 2-Methyl-1-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

872-32-2, Intermediate 1: Methyl 3-chloro-lH-pyrrole-2-carboxylate At 55-60 ¡ãC with vigorous stirring to a mixture of NCS (107 g, 800 mmol) in THF (250 mL) in a 2 L flask was added 5-methyl-3,4-dihydro-2H-pyrrole (8.3 g, 100 mmol) in one-portion. After addition, the reaction spontaneously heated to reflux for about 5 min, then reacted at 60-70 ¡ãC for another 1.5 hours. After cooled to r.t., hexane (300 mL) and water (300 mL) were added to the mixture. The organic layer was separated, collected and concentrated. The residue was used in the next step without further purification. To a mixture of the crude 4,4-dichloro-5-(trichloromethyl)-3,4-dihydro-2H-pyrrole (240 g, 941 mmol) in MeOH (2 L) in an ice-bath was added a solution of NaOMe (324 g, 6 mol) in MeOH (1.5 L) drop-wise over an hour. After addition, the mixture was stirred at r.t. for another one hour. Then 2N HCl aq. was added to adjust its pH to 2 and the resulting was stirred at room temperature for 15 minutes. The mixture was concentrated and diluted with EtOAc (2.5 L) and water (2 L). The organic layer was separated, concentrated and purified by column chromatography eluting with EtOAc/PE and then crystallize upon standing. Methyl 3-chloro-lH-pyrrole-2-carboxylate was obtained as an orange solid (91.3 g, yield: 61percent). MS (m/z): 160.1 (M+H)+ . 1H NMR (400 MHz, DMSO-de) delta 12.05 (s, 1H), 6.98 (m, 1H), 6.21 (t, / = 2.6 Hz, 1H), 3.75 (s, 3H).

The synthetic route of 872-32-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15675; (2014); 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.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.

5-Methyl-3,4-dihydro-2H-pyrrole (60.2 mmol, 1.0 equiv.) was dissolved in CCl4 (100 ml); at 0¡ã C., N-chlorosuccinimide (8.0 equiv.) was added in portions, and the mixture was heated for 72 h at boiling temperature. The reaction mixture was cooled to 0¡ã C., and the resulting solid was filtered out and washed with cooled (0¡ã C.) CCL4 (2.x.50 ml). The filtrate was concentrated to dryness under reduced pressure. Yield: 90percent, 872-32-2

The synthetic route of 872-32-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gruenenthal GmbH; US2010/222324; (2010); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

55750-48-6, Methyl 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,55750-48-6

A solution of amine 6 (17.8 mg, 0.04 mmol) in 1 M aqueous solution of NaHC03 (1 mL) was treated with methoxycarbonylmaleimide (37.94 mg, 0.24 mmol) at 0 [C.] After 5 min, the mixture was diluted with water [(1] mL) and acetonitrile (2 [ML),] and then stirred at room temperature for 4 h. After adding [CH2C12] (50 [ML),] the organic layer was separated and washed with brine [(3X10] mL). The organic layer was then dried [(NA2SO4),] filtered, and concentrated. The oily residue was purified by flash chromatography (CH2Cl2/MeOH 95: 5) to give maleimide 7 (23.2 mg, 76%); Rf 0. 42 [(CH2CI2/MEOH] 95: 5) [; IH-NMR (CDCL3/TMS)] : [No.6. ]70 (s, 2 H, CH=CH), 6.69 (s, 4 H, CH=CH), 6.68 (s, 2 H, CH=CH), 4.98 (d, [1] H, [J=3.] 4 Hz, H-1), 3.95-3. 82 (m, 2 H, H-4, and [OCHHCH2CH2N),] 3. [80No.3. ] 35 (m, 22 H, H-2, H-3, H-5, H-6, H-6′, [OCH2CH2CH2N,] [OCH2CH2CH2N,] and [OCH2CH3),] 1.96-1. 78 (m, 8 H, [OCH2CH2CH2N),] 1.25 (t, 3 H, J=7.1 Hz, [OCH2CH3)] ; ES-MS: 779.28 (M+Na) [+,] 401.29 (M+2Na) [2+.]

55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE; WO2004/802; (2003); A2;,
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.872-32-2,2-Methyl-1-pyrroline,as a common compound, the synthetic route is as follows.

872-32-2, 5-methyl-3,4-dihydro-2H-pyrrole (4 g, 0.05 mol) was dissolved in THF (120 mL) and N-chlorosuccinimide (51.4 g, 0.39 mol) was slowly added at 0 ¡ã C and refluxed for 15 minutes. The reaction mixture was stirred at 70 & lt; After stirring for two and a half hours, the THF was removed under reduced pressure, extracted three times with dichloromethane and washed with brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain 4,4-dichloro-5- (trichloromethyl) -3,4-dihydro-2H-pyrrole.It was used immediately for the next reaction without further purification. 4,4-Dichloro-5- (trichloromethyl) -3,4-dihydro-2H-pyrrole (2 ) (12 g, 0.05 mol) To methanol (100 mL) was added And dissolved in sodium methoxide (NaOMe) (28 wtpercent methanol) (16 g, 0.29 mol) is slowly added dropwise at 0 . The reaction mixture was reacted at room temperature for 2 hours, extracted three times with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The reaction mixture was purified by flash column chromatography (n-hexane: ethyl acetate = 5: 1) Purification yielded 6.5 g (0.04 mol, 77percent yield) of brown solid compound methyl 3-chloro-lH-pyrrole-2-carboxylate.

As the paragraph descriping shows that 872-32-2 is playing an increasingly important role.

Reference£º
Patent; Korea Research Institute of Chemical Technology; Lee, Gay Hyung; Lim, Hee Jong; Cho, Hee Young; Park, Woo Kyu; Jung, Dae Young; (40 pag.)KR2017/74381; (2017); 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.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/(2S)-2-amino-4-[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]-N-{2-[(2-{[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl]amino}ethyl)sulphonyl]ethyl}butanamide (1:1) The title compound was prepared from Intermediate L81 by coupling with Intermediate C58 in the presence of HATU and N,N-diisopropylethylamine. In the next step, the Z protective group was removed by hydrogenation over 10% palladium on activated carbon in DCM/methanol 1:1 at RT under hydrogen standard pressure for 30 min. The deprotected intermediate was then converted by coupling with (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid in the presence of HATU and N,N-diisopropylethylamine and finally by deprotection with zinc chloride into the title compound. LC-MS (Method 1): Rt=0.83 min; MS (ESIpos): m/z=785 (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; 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

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, In a Biotage Initiator 2-5 mL vial, nitrone 1 (392 mg, 1.64 mmol) and N-benzyl-3-pyrroline 2 (314 mg, 1.97 mmol, 1.2 eq) were introduced. The vial was flushed with argon and 2.5 mL of anhydrous toluene was added (c = 0.66 mM). The vial was sealed with a septum cap and was sonicated for 20 s. The resulting mixture was irradiated by microwaves (temperature: 140 C). TLC monitoring (EtOAc) showed full conversion after 2 h. After the crude mixture was concentrated, the crude product was purified by flash silica gel column chromatography (EtOAc) to afford cycloadduct 3 (625 mg, 1.57 mmol, 96%) with no traces of other isomer. Monocrystals ofcompounds 3 were obtained from a saturated Et2O solution cooledin a freezer. Rf 0.48 (EtOAc). [a]D 40.4 (c 1.1, CH2Cl2). 1H NMR(400 MHz, CDCl3) d 7.37e7.20 (m, 5H, CH-ar), 4.59 (td,1H, J 7.0 Hz,J 3.0 Hz, H-4), 3.71e3.49 (m, 3H, NCH2Ph, H-6), 3.42 (dd, 1H,J 10.3 Hz, J 6.6 Hz, H-3), 2.78 (dd, 1H, J 10.3 Hz, J 3.0 Hz, H-5), 2.75e2.69 (m, 4H, NCH3, H-2), 2.65 (dd, 1H, J 9.4 Hz, J 3.7 Hz,H-20), 2.58 (dd, 1H, J 9.9 Hz, J 6.6 Hz, H-50), 2.14e2.08 (m, 1H, H-9), 2.00 (dtt, 1H, J 12.9 Hz, J 6.5 Hz, J 3.3 Hz, H-10), 1.90e1.78(m, 2H, H-11, H-12), 1.68e1.59 (m, 1H, H-120), 1.48 (dt, 1H,J 13.5 Hz, J 6.7 Hz, H-15), 1.38 (dd, 1H, J 12.1 Hz, J 3.2 Hz, H-13), 1.18 (t, 1H, J 12.3 Hz, H-90), 0.95e0.85 (m, 10H, H-11?, H-14, H-16). 13C NMR (100 MHz, CDCl3) d 172.8 (C]O), 138.9 (C-ar), 128.6(CH-ar), 128.3 (CH-ar), 127.1 (CH-ar), 88.0 (C-8), 79.6 (C-4), 71.9 (C-6), 59.6 (NCH2Ph), 59.4 (C-5), 59.3 (C-2), 49.1 (C-3), 48.2 (C-13), 41.0(C-9), 35.0 (C-11), 29.0 (C-10), 25.9 (NCH3), 24.5 (C-15), 24.2 (CH3),22.6 (C-12), 22.4 (CH3), 18.7 (CH3). HR-ESI-QToF MS (positivemode): m/z calcd for C24H36N3O2 [MH]: 398.2802, found:398.2806.

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

Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
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

[0573] N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide (28 mg, 0.146 mmol, 1 eq) was added to a solution of 95 (203 mg, 0.146 mmol) and maleimide-PEGs 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/10% methanol] gave 96 as a pale yellow solid (205 mg, 72%). LC/MS, System 1: RT 5.75 min; MS (ES+) m/z (relative intensity) 982.90 (100), 1963.70 (5)., 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; MEDIMMUNE LIMITED; LLOYD, Christopher O.; MARWOOD, Rose; HOWARD, Philip; HARPER, III, John W.; HOLLINGSWORTH, Robert; KAMAL, Adeela; DIMASI, Nazzareno; GAO, Changshou; TOADER, Dorin; WANG, Fengjiang; GINGIPALLI, Lakshmaiah; WO2015/155345; (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.151038-94-7,6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide 2,2,2-trifluoroacetate,as a common compound, the synthetic route is as follows.

[00250] Acetoxycisplatin(4-acetylphenyl)carboxylate (178 mg, 0.341 mmol, 1 equiv) was dissolved in DMF (0.05 M, 6.8 mL) and treated with 6-(2,5-dioxo-2,5- dihydro-1 H-pyrrol-1 -yl)hexanehydrazide TFA salt (139 mg, 0.409 mmol, 1 .2 equiv). The reaction mixture was stirred at room temperature for 5 hours. MTBE was added to the reaction mixture until a suspension was obtained and a yellow solid was filtered to afford compound 17 (159 mg, 64%, 97% pure). 1H NMR (500 MHz, DMF-d7) delta 10.48 (s, 0.3H), 10.40 (s, 0.6H), 7.97-7.92 (m, 2H), 7.91 -7.86 (m, 2H), 7.24-6.77 (m, 6H), 7.02 (s, 2H), 3.50-3.44 (m, 2H), 2.77-2.72 (m, 1 .4H), 2.44-2.38 (m, 0.6H), 2.40 (s, 2H), 2.37 (s, 1 H), 1 .94 (s, 3H), 1 .73-1 .64 (m,2H), 1 .63-1 .54 (m, 2H), 1 .42-1 .29 (m, 2H); HPLC-MS 98%, m/z for CziHzgC NsOyPt [(M+H)+] = 730.2.

151038-94-7, 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 fields.

Reference£º
Patent; BLEND THERAPEUTICS, INC.; MOREAU, Benoit; BILODEAU, Mark T.; WHALEN, Kerry; MEETZE, Kristan; SINGH, Sukhjeet; WOOSTER, Richard; LEMELIN, Charles-Andre; (139 pag.)WO2015/200250; (2015); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem