Heterocyclic Building Blocks-Pyrrolines

5264-35-7, 5-Methoxy-3,4-dihydro-2H-pyrrole is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 2-(Dimethylaminoethylamino-1-pyrroline Into a solution of 4.4 gm. (0.05 mole) of N,N-dimethylethylene diamine in 15 ml. of methanol with cooling is added 3.6 gm. (0.1 mole) of hydrogen chloride gas and then at room temperature is added 5.6 gm. (0.05 mole) of 88percent 2-methoxy-1-pyrroline and let stir at ambient temperature for 221/2 hours. Removed the methanol, dissolved the residue in water, neutralized with sodium hydroxide and extracted with methylene chloride, dried and evaporated affording 8.0 gm. of 2-(dimethylaminoethylamino)-1-pyrroline.

5264-35-7 5-Methoxy-3,4-dihydro-2H-pyrrole 353443, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; Merck & Co., Inc.; US4241072; (1980); 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.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 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; WO2015/52534; (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.69778-83-2,4-Methoxy-1H-pyrrol-2(5H)-one,as a common compound, the synthetic route is as follows.

To a mixture of diethylformamide (3 eq, 5.8 mL) and chloroform (5 mL) at 00C was added dropwise a solution of phosphorus oxybromide (2.5 eq, 12.6 g) in chloroform (15 mL). The resulting suspension was stirred at 0 0C for 30 min, and the sol “vent was removed by rotary evaporation to obtain the Vilsmeier complex as a white solid. After drying in vacuo104USlDOCS 5506941vl EPO for 20 min, the solid was treated with chloroform (10 mL) and cooled to 0 0C. A solution of 4-methoxy-3-pyrrolin-2-one (A, 2 g, 17.7 mmol) in chloroform (20 mL) was added dropwise and the mixture was warmed to room temperature, then heated at 60 0C for 5h. The mixture was poured onto ice (75 mL), and the pH of the aqueous solution was adjusted to pH 7-8 by treatment with NaOH 2N. EtOAc (40 mL) was added to the resulting precipitate and the mixture was filtered over Celite.(R). to remove the black solid containing phosphorus salts.The two layers were separated and the aqueous layer was extracted with EtOAc (3 x 100 mL). The organic layers were combined, washed with brine (3 x 200 mL), dried over Na2SO4, filtered and the solvent was removed by rotary evaporation to furnish the crude enamine intermediate B’.The residue was filtered over a pad of silica gel (50 mL) using a 10percent EtOAC/Hexianes as eluent to obtain the enamine as an oil, which upon drying in vacuo lead to a beige solid.Yield: 3.20 g, 70percent. M/Z: 260.1 [M+l]RMNT 1H (300 MHz, CDCl3): delta (ppm) 1.24-1.37 (m, 6H); 3.31-3.46 (q, 2H); 3.76 (s, 3H), 4.03-4.18 (q, 2H); 5.58 (s, 3H); 6.98 (s, 3H).

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

Reference£º
Patent; GEMIN X BIOTECHNOLOGIES INC.; WO2006/89397; (2006); 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.6913-92-4,1-Benzyl-3-pyrroline,as a common compound, the synthetic route is as follows.

Example 16 2-benryl-5-tert butyl-1,2,3,3a-tetrahydrocyclopenta[c]pyrrol-4(6aH)-one. To a solution of 3,3-dimethyl-1-butyne (29 mg, 0.34 mmol) in 1,2-dichloroethane (1ml) cooled at 0C was added CO2(CO)8 (118 mg, 0.34 mmol) and the mixture was stirred 15 min at 0C and 40 minutes at room temperature. A solution of 1-benzyl-3-pyrroline (50 mg, 0.31 mmol) in 1,2-dichloroethane (1 ml) and dimethylsulfoxide (72 mul, 1.01 mmol) were added and the mixture was heated at 83C for 20 hours. The reaction mixture was filtered through celite and washed with CH2Cl2. The filtrate was concentrated and the crude was purified by flash chromatography: silica gel, dichloromethane, to afforded the product (11 mg, 13%) as yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 7.29-7.17 (m, 5H), 7.08 (d, J=3Hz, 1H), 3.59-3.47 (AB system, 2H), 3.17 (m, 1H), 3.04 (d, J=9Hz, 1H), 2.72 (m, 1H), 2.68 (d, J=9Hz, 1H), 2.35 (t, J=9Hz, 1H), 2.30 (t, J=9Hz, 1H), 1.20 (s, 9H). 13C NMR (75 MHz, CDCl3) delta (ppm) 209.28, 156.44, 154.52, 128.27, 128.19, 126.88, 58.69, 58.78, 56.15, 50.23, 42.00, 31.72, 28.33,. MS (El+) m/z: 269.17 (M+).

6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1849772; (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.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.

l-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI, 33 mg, 0.172 mmol) was added to a solution of crude 63 (0.172 mmol) and Mal-(PEG)g-acid (100 mg, 0.172 mmol) in dry dichloromethane (10 mL). The reaction was stirred for 2 hours and the presence ofstarting 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 64 (E) (60 mg, 25% over 3 steps).

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; 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

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 90 (77 mg, 63.4 mumomicronIota) in DMF (1 mL). The reaction mixture was allowed to stir for 20 minutes. The reaction mixture was carefully diluted with DCM (50 mL) and washed with water (50 mL). The organic layers was washed with brine (100 mL), dried over MgSO4, 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 mumomicronIota) and EDCI (18 mg, 95 mumomicronIota) 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 min (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 (MgS04), 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 CHCl3/MeOH to 90:10 v/v CHCl3/MeOH) gave 91 as a yellow solid (43 mg, 43%). 1H NMR (400 MHz, CDCI3) delta 8.73 (s, 1 H), 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, 1 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, 1 H), 4.72 – 4.63 (m, 1 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, 1 H), 2.59 (s, 4H), 2.55 – 2.43 (m, 3H), 2.37 (s, 3H), 2.29 (dd, J = 12.7, 6.7 Hz, 1 H), 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 = 1 1 .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; 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

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.HCI (46 mg, 0.24 mmol) was added to a solution of 145 and Mal-PEG8-acid (130 mg,0.22 mmol) in CHCI3 (10 mL) and stirred at room temperature for 2 hr. LC/MS shows 78%starting material present. A further 2 eq EDCI.HCI was added in portions to push the reaction to completion. The reaction mixture was washed with water (10 mL), dried (Biotage PS) and evaporated to dryness, under reduced pressure, to leave a yellow solid which was purified by prep HPLC to leave the product I as an off-white solid (90 mg, 34%yield). LC/MS (method B): retention time 1.47 mins, (ES+) rnlz 1445.9 [M+ H].

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

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 DM F (1 mL). The reaction mixture was allowed to stir for 20 minutes. The reaction mixture was carefully diluted with DCM (50 mL) and washed with water (50 mL). The organic layers was washed with brine (100 mL), dried over MgS04, 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 min (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 (MgS04), 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 CHCIs/MeOH) gave 26 as a yellow solid (43 mg, 43%). 1H NMR (400 MHz, CDCI3) delta 8.73 (s, 1 H), 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, 1 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, 1 H), 4.72 – 4.63 (m, 1 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, 1 H), 2.59 (s, 4H), 2.55 – 2.43 (m, 3H), 2.37 (s, 3H), 2.29 (dd, J = 12.7, 6.7 Hz, 1 H), 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 = 1 1 .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; HOWARD, Philip Wilson; TIBERGHIEN, Arnaud; CAILLEAU, Thais; WO2015/52321; (2015); A1;,
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

In 150 mL beaker, compound F1 (0.5 g, 0.0023 mmol), 20 mLof dimethyl sulfoxide (DMSO) and 0.034 mmol of SOCl2 weremixed and heated on hot plate using magnetic stirrer at 20 C,and then added triethylamine (1.815 g, 0.0179 mmol) after 20min. Finally, added sulfadiazine (0.575 g, 0.0023 mmol/chlorodizepoxide (0.688 g, 0.0023 mmol) into the mixture with constantstirring at 30 C for 30 min. The mixture was cooled on icebath and leave until the precipitate was formed, filtered and drythe product (Schemes II and III) [22]. The reaction processwas monitored by TLC.

As the paragraph descriping shows that 17057-04-4 is playing an increasingly important role.

Reference£º
Article; Mageed, Fatimah Abdul Razzak; Kareem, Mohanad Musa; Al-Baiati, Mohammad N.; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 569 – 574;,
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

5-methyl-3,4-dihydro-2H-pyrrole(1) (4 g, 0.05 mol) was dissolved in THF (120 ml), to which N-chlorosuccinimide (51.4 g, 0.39 mol) was slowly added at 0¡ã C. The mixture was stirred for 15 minutes, followed by reflux for 2.5 hours. THF was eliminated under reduced pressure. Extraction was performed with dichloromethane. The organic layer was washed with saturated brine, separated, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The obtained compound 4,4-dichloro-5-(trichloromethyl)-3,4-dihydro-2H-pyrrole(2) was used for the next reaction without purification. 4,4-dichloro-5-(trichloromethyl)-3,4-dihydro-2H-pyrrole(2) (12 g, 0.05 mol) was dissolved in methanol (100 ml), to which sodium methoxide (NaOMe) (28 wt percent methanol solution) (16 g, 0.29 mol) was slowly added at 0¡ã C., followed by reaction at room temperature for 2 hours. Extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, separated, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: hexane/ethyl acetate, 5/1) to give 6.5 g of the target compound methyl 3-chloro-1H-pyrrole-2-carboxylate(3) as a brown solid (0.04 mmol, yield: 77percent). 1H NMR (300 MHz, CDCl3) delta 9.11 ( br s, 1H, NH), 6.87 (t, J=2.7 Hz, 1H), 6.26 (t, J=2.7 Hz, 1H), 3.90 (s, 3H).

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

Reference£º
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem