Category: pyrrolines

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.

N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide (28 mg, 0.146 mmol, I eq) was added to asolution of 42 (203 mg, 0.146 mmol) and maleimide-PEG8 acid (87 mg, 0.146 mmol) inchloroform (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/I0% methanol] gave 43 as a pale yellow solid (205 mg, 72%). LC/MS: RT 5.75 mm; MS (ES+)m/z (relative intensity) 982.90 (100), 1963.70 (5)., 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

2973-17-3, 1-Allyl-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A solution of 2.5 mmol of 3-N-methylcytisine 2 and 12.5 mmol of N-substituted maleimide in 10 ml of toluene was refluxed under AP until the starting reactant disappeared (TLC monitoring). Then the solvent was evaporated in vacuo. The crude product was chromatographed on SiO2 with a mixture of CHCl3 and CH3OH as the eluent to afford a-adduct and b-adduct. (3aS,4R,8S,12S,12aR,12bS)-2-allyl-10-methyloctahydro-1H- 4,12a-etheno-8,12-methanopyrrolo[3?,4′:3,4]pyrido[1,2-a][1,5] diazocine-1,3,5(4H)-trione 19a and 1(3aR,4S,8S,12S,12aS,12bR)-2- allyl-10-methyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo [3?,4′:3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione 19b. Compounds 19a (0.146 g) and 19b (0.122 g) were obtained from 0.2 g of 2 (1 mmol) and 0.68 g of 8 (5 mmol) in a 80% total yield. 19a: White crystals, m.p. 148-150 C (EtOAc), [a]20D = 11.0 (c 1.6, CHCl3). 13C NMR (CDCl3, d, ppm): 25.55 (C15); 26.76 (C8); 33.69 (C12); 40.99 (C10); 41.62 (C3a); 45.17 (C4); 46.56 (C100); 47.35 (C12b); 47.54 (C7); 58.11 (C11); 62.28 (C9); 63.71 (C12a); 118.58 (C30); 130.06 (C14); 130.27 (C20); 139.83 (C13); 172.56 (C5); 174.91 (C1); 175.40 (C3). 15N NMR (CDCl3, d, ppm): 124.94 (N6); 184.00 (N2). 1H NMR (CDCl3, d, ppm, J Hz): 1.72 (br.s, 2H, H-15); 2.16 (m, 1H, Hb-11); 2.17 (m, 1H, Hb-9); 2.20 (m, 1H, H-8); 2.23 (s, 3H, H-100); 2.49 (m, 1H, H-12); 2.80 (br.d, 1H, 2J = 11.5, Ha-9); 3.32 (dd, 1H, 2J = 13.2, 3J7b-8 = 7.1, Hb-7); 3.34 (dd, 1H, 3J3a-12b = 8.0, 3J3a-4 = 3.4, H-3a); 3.40 (br.d, 1H, 2J = 13.2, Ha-7); 3.67 (br.d, 1H, 2J = 12.3, Ha-11); 3.85 (d, 1H, 3J12b-3a = 8.0, H-12b); 3.89 (ddd, 1H, 3J4-14 = 6.0, 3J4-3a = 3.2, 4J4- 13= 1.4, H-4); 4.00 (dt, 2H, 3J1′-2′ = 6.0, 4J1′-3’A(3’B) = 1.6, H-1?); 5.16 (qd, 1H, 2J = 1.6, 3J3’A 2′ = 10.0, 4J3’A 1′ = 1.6, HA-3?); 5.19 (qd, 1H, 2J = 1.6, 3J3’B 2′ = 17.1, 4J3’B 1′ = 1.6, HB-3?); 5.67 (ddt, 1H, 3J2′-3’B = 17.1, 3J2′-3’A = 10.0, 3J2′-1′ = 6.0, H-2?); 6.22 (dd, 1H, 3J13-14 = 7.5, 4J13-4 = 1.4, H-13); 6.31 (dd, 1H, J14-13 = 7.5, J14-4 = 6.0, H-14).

2973-17-3, 2973-17-3 1-Allyl-1H-pyrrole-2,5-dione 18098, apyrrolines compound, is more and more widely used in various fields.

Reference£º
Article; Tsypysheva, Inna; Koval’skaya, Alena; Petrova, Polina; Lobov, Alexander; Borisevich, Sophia; Tsypyshev, Dmitry; Fedorova, Victoria; Gorbunova, Elisaveta; Galochkina, Anastasia; Zarubaev, Vladimir; Tetrahedron; vol. 75; 21; (2019); p. 2933 – 2943;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

766-36-9,766-36-9, 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

3-Ethyl-4-methyl-3-pyrrolin-2-one (300mg , 2.4mM), 2-Bromo-4-trifluoromethylpyridine (452 mg,2.0 mM), tris(dibenzylideneacetone)dipalladium (0) (37 mg, 0.04mM), xantphos (173 mg, 0.3mM) and caesium carbonate (978 mg, 3 mM) were dissolved in dioxane (5 mL), and heated in asealed vessel under nitrogen at 100 ¡ãC for 30 minutes in a microwave. The mixture was allowedto cool to ambient temperature, partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous phase was extracted with further ethyl acetate (2 x 20 mL). The ethyl acetate extracts were combined, washed with water (30 mL), dried over magnesium sulfate, filtered and evaporated to give N-(4-trifluoromethylpyrid in-2-yl )-3-m ethyl-4-ethyl-5-oxo-2 ,5-d ihyd ropyrrole asa yellow oil. This was purified by chromatography on silica to give 490 mg of a yellow oil that crystallised1H NMR (CDCI3), 8.80 (d, 1H), 8.45 (d, 1H), 7.19 (dd, 1H), 4.45 (s, 2h), 2.35 (q, 2H), 2.10 (s, 3H), 1.13 (t, 3H).

The synthetic route of 766-36-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SYNGENTA PARTICIPATIONS AG; MORRIS, James Alan; HENNESSY, Alan Joseph; BOEHMER, Jutta Elisabeth; (99 pag.)WO2016/71360; (2016); 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

EDCI hydrochloride (8 mg, 0.042 mmol) was added to a suspension of Maleimide-PEG8-acid(25 mg, 0.042 mmol) in dry CH2CI2 (4 mL) under argon atmosphere. PBD 19 (42 mg, crude)was added straight away and stirring was maintained until the reaction was complete (3hours). The reaction was diluted with CH2CI2 and the organic phase was washed with H20 and brine before being dried over MgSO4, 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 CHCI3/MeOH) followed by reverse phase HPLC to remove unreacted maleimide-PEG8-acid. The product 20 was isolated in 10% over two steps (6.6 mg). LC/MS 1.16 mm (ES+) m/z (relative intensity) 770.20 ([M + 2H], 40%).

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; WO2015/52535; (2015); 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

7544-75-4, 2-Phenyl-6,7-dihydro-5H-pyrrolo[1, 2-a] imidazole; Combine 2-iminopyrrolidine hydrochloride (6. 98 g, 57. 8 mmol) (Callahan, et al., (at) J. Med. Chem. 45, 999-1001 (2002)), 2-bromoacetophenone (3. 8 g, 19. 3 mmol), and sodium carbonate (8. 2 g, 77. 2 mmol) in dry dimethylformamide (25 mL). Heat at 80C for 18 hours. Cool to room temperature, add water (60 mL), and extract with ethyl acetate (3 x 100 mL). Concentrate the combined organic layers under reduced pressure. Dilute the residue with diethyl ether (100 mL), wash with cold water (3 x 80 mL), and concentrate under reduced pressure to provide the desired compound as a white solid (3. 2 g, 89 %). MS (ES) : m/z = 185. 1 (M++H)

The synthetic route of 7544-75-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/80380; (2005); 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.,73286-71-2

Reference Example 2; tert-Butyl (3aR*,4R*,9bR*)-4-phenyl-2,3,3a,4,5,9b-, hexahydro-lH-pyrrolo[3,2-c]quinoline-l-carboxylate and tert-butyl (3aR*,4S*,9bR*)-4-phenyl-2,3,3a,4,5,9b- hexahydro-1H-pyrrolo[3,2-c(at)quinoline-1-carboxylate; Benzaldehyde (2.92 g, 28 mmol), aniline (2.56 g, 28 mmol), tert-butyl 2,3-dihydro-lH-pyrrole-l-carboxylate (3.4 g, 25 mmol) and Dy (OTf)3 g, 1.38 mmol) were stirred in acetonitrile (50 ml) at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (anhydrous MgS04), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (150 g), and eluted with hexane-ethyl acetate (4: 1, v/v). The title compound (3aR*,4R*,9bR*) (2.7 g, 31%) was obtained as an amorphous form from the first eluted fraction. (at)H-NMR (CDCl3)No.: 1.42-1.62 (10H, m), 2.08-2.28 (1H, m), 2.52-2.59 (lH, m) , 3.32-3.49 (2H, m) , 3.92 (lH, m) , 4.74 (lH, m), 5.36 (lH, dd, J=42.8,7.0 Hz), 6.58 (1H, d, J=8.1 Hz), 6.78 (lH, m), 6.98-7.13 (lH, m), 7.23-7.49 (5H, m) , 7.55-7.72 (lH, m) . LC/MS (ESI) m/z: 351 (MH(at)). The title compound (3aR*,4S*,9bR*) (4.0 g, 46%) was obtained as an amorphous form from the second eluted fraction. ? H-NMR (CDCl3) No.: 1.49 (9H, s), 2.03-2.13 (2H, m), 2.54- 2.64 (lH, m), 3.31-3.39 (lH, m), 3.50 (lH, br s), 4.21- 4.24 (lH, m), 4.35-4.38 (lH, m), 4.83 (lH, br s), 6.57 (lH, d, J=7.6 Hz), 6.65-6.79 (lH, m), 7.05-7.34 (6H, m), 7.49 (lH, s). LC/MS (ESI) m/z: 351 (MH(at)).

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/105802; (2005); 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.17057-04-4,4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid,as a common compound, the synthetic route is as follows.

23.0 mL (2216.4 mmol) of toluene, 5.0 g (22.8 mmol) of 4-maleimidebenzoic acid, 2.2 mL (30.4 mmol) of thionyl chloride, and 4 mL of toluene were placed in a 100 mL three-necked flask equipped with a stirrer and a cooling tube,0.36 mL (4.6 mmol) of N, N-dimethylformamide was added,And the mixture was stirred at 80 DEG C for 1 hour in a nitrogen atmosphere to complete the chlorination reaction. Thereafter, the volatile components were removed by distillation under reduced pressure,Maleimide benzoic acid chloride was obtained as yellowish white crystals.Then, 5.4 g (22.8 mmol) of the obtained 4-maleimide benzoic acid chloride,40.0 mL (353.7 mmol) of O-dichlorobenzene,2.0 g (5.7 mmol) of the compound (1)3.2 mL (22.8 mmol) of triethylamine was stirred for 1 hour while heating at 80 DEG C under a nitrogen atmosphere to complete the esterification reaction. Thereafter, the reaction solution was cooled to room temperature, the precipitate was collected, washed with methanol, and dried to obtain 4.1 g (5.5 mmol) of the compound (2) as yellowish white crystals. The obtained compound (2) was identified by chemical analysis to have a chemical structure represented by the following formula (1-1) (molecular weight: 748.7). It was also confirmed that the compound (2) exhibited thermotropic liquid crystallinity by observation under a polarizing microscope. Further, it was confirmed that the compound (2) showed good solubility in DMSO, DMF and NMP.

17057-04-4, The synthetic route of 17057-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Da I Sel Co., Ltd.; Na Ka-ta-ni-, -go-u-ji; I No-u-e-, -ge-i-jo; (17 pag.)KR2018/130526; (2018); 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.205444-34-4,(S)-tert-Butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

Boron tribromide (BBr3 12 ml; 1 M in CH2Cl2) was slowly added to a stirred solution of 3-Iodo-5-methoxypyridine (10, 471 mg; 2 mmol) in CH2Cl2 (10 ml) at -40 C (dry ice bath) and reaction mixture was left overnight stirring with gradual warming to ambient temperature. MeOH (7 ml) was slowly added and the reaction mixture was refluxed for 2 h. After removal of solvent, water was added and pH was adjusted to 7-8 by adding Na2CO3. The reaction mixture was extracted with EtOAc, dried over Na2SO4 and concentrated to yield crude product which was purified by prep-TLC using EtOAc/hexanes (1:3) to furnish 3-iodo-5-hydroxypyridine, 11 (300 mg, 68%) as a solid compound. To a solution of 6 (0.20 g, 1.0 mmol), 3-iodo-5-hydroxypyridine (11, 0.24 g, 1.1 mmol) and triphenylphosphine (0.40 g, 1.5 mmol) in THF (10 mL), stirred under argon and cooled at 0 C, was added diisopropyl azodicarboxylate (DIAD; 0.3 mL, 1.5 mmol). The reaction mixture was allowed to come up to ambient temperature over a period of 2 h and was stirred overnight. The reaction mixture was evaporated to dryness and the residue was purified by preparative TLC (30% EtOAc in hexane) to give pure product 12 (0.20 g, 50%) as an oil. 1H NMR (500 MHz, CDCl3) delta ppm: 8.41(d, J = 15.0, 1H, PyH), 8.25 (d, J = 2.0, 1H, PyH), 7.56 (d, J = 18.5, 1H, PyH), 5.88 (m, 2H, olefinic), 4.80 (m, 1H, CH-CH2), 4.34-3.95 (m, 4H, O-CH2, N-CH2), 1.48 (s, 9H, Boc). MS, m/z, 403 (100%, [M+H]+).

205444-34-4, As the paragraph descriping shows that 205444-34-4 is playing an increasingly important role.

Reference£º
Article; Pandey, Suresh K.; Pan, Shawn; Kant, Ritu; Kuruvilla, Sharon A.; Pan, Min-Liang; Mukherjee, Jogeshwar; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7610 – 7614;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

6913-92-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

N-Benzyl-3-pyrroline 2 (504 muL, 2.64 mmol) was added to a solution of ethyl chlorooximidoacetate (1 g, 6.62 mmol, 2.5 eq) in toluene (20 mL). The flask was heated to 110 C (oil bath) while a solution of Et3N (276.8 muL, 19.8 mmol, 7.5 eq) in toluene (15 mL) was added over 16 hh using a syringe pump. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography (4:1 petroleum ether/EtOAc) to afford compound (+-)-20 (370 mg, 1.35 mmol, 51%). Yellow oil Rf = 0.52 (7:3 petroleum ether/EtOAc). 1H NMR (400 MHz, CDCl3): delta 7.26 (m, 5H, phenyl), 5.20 (dd, 1H, J5,4 = 4.5 Hz, J3,4 = 9.6 Hz, H-4), 4.31 (2 complex q, 2H, J = 7.2 Hz, diastereotopic OCH2), 3.91 (dt, 1H, J2′,3 = 1.0 Hz, J2,3 = 7.1 Hz, J3,4 = 9.5 Hz, H-3), 3.68 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.55 (d, 1H, 2J = 13.3 Hz, NCH2Ph), 3.24 (d, 1H, 2J = 11.2 Hz, H-5′), 3.19 (d, 1H, 2J = 9.9 Hz, H-2′), 2.44 (dd, 1H, J2,3 = 7.2 Hz, 2J = 9.8 Hz, H-2), 2.37 (dd, 1H, J5,4 = 4.6 Hz, 2J = 11.2 Hz, H-5), 1.31 (t, 3H, J = 7.2 Hz, Me). 13C NMR (100 MHz, CDCl3): delta 160.7, 152.2 (C=N, C=O), 137.8 (C-ar), 128.5 (2CH-ar), 128.2 (2CH-ar), 127.1 (1CH-ar), 87.4 (C-4), 61.9 (OCH2), 61.1 (C-5), 58.3 (CH2 benzyl), 56.9 (C-2), 51.0 (C-3), 14.1 (CH3). MS m/z = 274.13 for C15H18N2O3; MS-ESI positive mode: 275.1 [M+H]+, 297.1 [M+Na]+.

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

N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide (28 mg, 0.146 mmol, 1 eq) was added to a solution of 105 (203 mg, 0.146 mmol) and maleimide-PEG8 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 106 as a pale yellow solid (205 mg, 72%). LC/MS: RT 5.75 min; MS (ES+) m/z (relative intensity) 982.90 (100), 1963.70 (5).

1334177-86-4, As the paragraph descriping shows that 1334177-86-4 is playing an increasingly important role.

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