Heterocyclic Building Blocks-Pyrrolines

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

First, in analogy to the synthesis described in Intermediate 75, by coupling of N-(tert-butoxycarbonyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-2-carboxy-1-methoxypropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Intermediate 26) and (1S,2R)-1-amino-2-phenylcyclopropanecarboxylic acid trifluoroacetate (Intermediate 207) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate and subsequent detachment of the Boc protecting group by means of trifluoroacetic acid, the amine compound N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-carboxy-2-phenylcyclopropyl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide was prepared as the trifluoroacetate. [2324] To 22 mg (0.026 mmol) of this compound in 10 ml of methanol were then added 17 mg (0.05 mmol) of 9H-fluoren-9-ylmethyl 6-oxohexyl carbamate (Intermediate 208) and 2.3 mg of acetic acid, and also 11.4 mg (0.12 mmol) of borane-pyridine complex. The reaction mixture was stirred at RT overnight. Then the same amounts of borane-pyridine complex and acetic acid, and also 8 mg of fluoren-9-ylmethyl 6-oxohexyl carbamate, were added once again and the reaction mixture was stirred at RT for a further 24 h. This was followed by concentration under reduced pressure, and the residue was purified by means of preparative HPLC. After concentration of the corresponding fractions, the product was used immediately in the next stage. 33 mg of the still contaminated intermediate were taken up in 5 ml of DMF, and 1 ml of piperidine was added. After stirring at RT for 15 min, the reaction mixture was concentrated and the resulting residue was purified by preparative HPLC. Thus, 11 mg (55% of theory over 2 stages) of the aminocarboxylic acid intermediate were obtained. [2325] HPLC (Method 12): Rt=1.7 min; [2326] LC-MS (Method 11): Rt=0.7 min; MS (ESIpos): m/z=843 (M+H)+. [2327] 6 mg (7.12 mumol) of this intermediate were taken up in 1 ml of dioxane and then admixed with 6.6 mg (42.7 mumol) of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate and with 5 mul of saturated aqueous sodium hydrogencarbonate solution. The reaction mixture was stirred at RT for 1 h. Then another 3 portions each of 50 mul of the saturated aqueous sodium hydrogencarbonate solution were added and the reaction mixture was stirred at RT for a further 30 min. Then the reaction mixture was acidified to pH 2 with trifluoroacetic acid and subsequently concentrated under reduced pressure. The remaining residue was purified by means of preparative HPLC. After lyophilization from acetonitrile/water, 4 mg (60% of theory) of the title compound were obtained as a foam. [2328] HPLC (Method 12): Rt=1.9 min; [2329] LC-MS (Method 11): Rt=0.88 min; MS (ESIpos): m/z=923 (M+H)+

The synthetic route of 55750-48-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lerchen, Hans-Georg; Hammer, Stefanie; Harrenga, Axel; Kopitz, Charlotte Christine; Nising, Carl Friedrich; Sommer, Anette; Stelte-Luowig, Beatrix; Mahlert, Christoph; Schuhmacher, Joachim; Golfier, Sven; Greven, Simone; Bruder, Sandra; US2015/23989; (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.31970-04-4,Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

Example 14; 8-(Y cis)-4-fluoropyrrol idin-3 -yloxy)-2-f 7-f 2-methoxyethoxy)imidazo fl,2-a1 pgammaridin-3 – yl)quinoline hydrochloride salt; Step A: Preparation of benzyl -oxa-S-azabicyclop.l.OJhexane-S-carboxylate:; Benzyl 2,5-dihydro-lH-pyrrole-l-carboxylate (11.0 g, 54.1 mmol, commercially available from Aldrich) and 3-chlorobenzoperoxoic acid (17.3 g, 70.4 mmol) were added to 150 mL of chloroform and heated to 46 0C for 20 hours. The mixture was cooled, dichloromethane was added, and the reaction was washed with a saturated solution OfNaHCO3 and Na2S2CO3. The combined organic layers were dried over MgSO4, filtered and concentrated to give 10.5 g (88% isolated yield) of the desired compound as an oil, which was used directly in the next step., 31970-04-4

As the paragraph descriping shows that 31970-04-4 is playing an increasingly important role.

Reference£º
Patent; ARRAY BIOPHARMA INC.; WO2008/124323; (2008); 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.,872-32-2

EXAMPLE 5Preparation of 6-{2-[2-(2-chlorophenyl)ethyl]pyrrolidin-1-yl}-9H-purine (“A5”)5.1 3 ml of 1-methylpyrroline are dissolved in 25 nil of THF and deprotonated at -78¡ã C. for 30 minutes using 22.6 ml of BuLi (1 M in hexane). 6.5 g of 2-chlorobenzyl bromide are dissolved in 25 ml of THF and added dropwise at the temperature indicated. After 30 minutes, the mixture is allowed to warm to RT for 12 hours. For work-up, 50 ml of water are added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are dried over sodium sulfate, evaporated and purified by chromatography on silica gel, giving 4.5 g of 5-[2-(2-chlorophenyl)ethyl]-3,4-dihydro-2H-pyrrole as a colourless oil, which is employed in the next reaction; Rt.: 1.303 min; [M+H]+208.

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

Reference£º
Patent; Merck Patent GmbH; US2011/263561; (2011); 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.5264-35-7,5-Methoxy-3,4-dihydro-2H-pyrrole,as a common compound, the synthetic route is as follows.

5264-35-7, To 1-(2,3-dichlorophenyl)-2-(pyridin-3-yl)ethanamine (258 mg, 0.97 mmol) in methanol (5 mL) was added 5-methoxy-3,4-dihydro-2H-pyrrole (96 mg, 0.97 mmol) followed by acetic acid (2 drops). The mixture was heated at 70¡ã C. for 16 hours. The mixture was cooled to room temperature and methanol was removed. Purification by chromatography on silica gel (5percent 7N NH3 in MeOH/CH2Cl2) gave N-(1-(2,3-dichlorophenyl)-2-(pyridin-3-yl)ethyl)-3,4-dihydro-2H-pyrrol-5-amine (161 mg, 50percent) as an off white solid.1H NMR (300 MHz, CD3OD) delta 1.79-1.90 (m, 2H), 2.41-2.49 (m, 2H), 2.87-2.94 (m, 1H), 3.14-3.21 (m, 1H), 3.34-3.41 (m, 2H), 5.28-5.33 (m, 1H), 7.30-7.47 (m, 4H), 7.77-7.81 (m, 1H), 8.36-8.42 (m, 1H), 8.43 (s, 1H).

As the paragraph descriping shows that 5264-35-7 is playing an increasingly important role.

Reference£º
Patent; ALLERGAN, INC.; US2010/145061; (2010); 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

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

31970-04-4, Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The title compound of Step 1 (3.0 g, 15 mmol) was dissolved in a mixture of acetonitrile (100 mL) and water (70 mL) containing ethylenediamine tetraacetate, disodium salt dihydrate (11 mg, 0.03 mmol). The solution was cooled to 0 C. and 1,1,1-trifluoroacetone (14.5 mL, 160 mmol) was added over 10 min. Potassium peroxymonosulfate (45 g, 74 mmol) was added portionwise over 40 min while maintaining the pH at 7 by adding sodium bicarbonate. The mixture was stirred at 0 C. for 1.5 hr then poured into water and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and concentrated to a colorless oil (3.45 g, 100%)., 31970-04-4

As the paragraph descriping shows that 31970-04-4 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2005/256310; (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.55750-48-6,Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

55750-48-6, Using a 40 mL vial, a solution of prop-2-yn-1 -amine (500 mg, 9.08 mmol) in 15 mL of sat. aqueous NaHC03 was cooled to 0 C with ice bath and then methyl 2,5-dioxo-2,5-dihydro-1 H- pyrrole-1 -carboxylate (1 .27 g, 8.17 mmol) was added. The reaction mixture was then stirred at the same temperature for 4 h and then extracted wtih 50 mL of CH2CI2 three times. The combined organic layers were dried over Na2S04, concentrated, purified by ISCO (24 g, silica gel) and concentrated to give 1 -(prop-2-yn-1 -yl)-1 H-pyrrole-2,5-dione (i-5). 1 H-NMR (CDCI3, 400 MHz) delta 6.76 (s, 2H), 4.29 (d, 2H, J = 2.8 Hz), 2.21 (t, 1 H, J=2.8 Hz).

The synthetic route of 55750-48-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; BURGER, Matthew T.; JIN, Yunho; UNO, Tetsuo; (202 pag.)WO2017/191579; (2017); 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.5264-35-7,5-Methoxy-3,4-dihydro-2H-pyrrole,as a common compound, the synthetic route is as follows.

5264-35-7, To a solution of ethyl N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]sulfamoylacetate dihydrochloride (0.52 g) obtained in example 59(a) in ethanol (5 ml) were added successively 5-methoxy-3,4-dihydro-2H-pyrrole (0.26 g), which was prepared from 2-pyrrolidinone according to the method described in Org. Prep. Proced. Int., 24, 147 (1992), and triethylamine (0.60 ml) at room temperature, and the resulting mixture was stirred at room temperature for 29 hours and then evaporated in vacuo.. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 25 percent acetonitrile/water).. Subsequently, to a solution of the amorphous solid obtained in ethanol (40 ml) was added a 4N solution of hydrogen chloride in dioxane (0.75 ml), and the resulting mixture was evaporated to dryness in vacuo.. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.43 g, yield: 77 percent) as a colorless amorphous solid. 1H NMR (400MHz, DMSO-d6) delta ppm: 1.23 (3H, t, J=7.0), 1.68-1.80 (2H, m), 2.00-2.14 (4H, m), 2.96 (2H, t, J=8.0), 3.46-3.87 (6H, m), 4.20 (2H, q, J=7.0), 4.34 (2H, s), 4.45 (2H, d, J=6.0), 4.67-4.73 (1H, m), 6.44 (1H, dt, J=16.0, 6.0), 6.55 (1H, d, J=16.0), 7.04 (2H, d, J=9.0), 7.39 (2H, d, J=9.0), 7.55 (1H, t, J=8.0), 7.68-7.73 (2H, m), 7.88 (1H, s); IR (KBr, cm-1): 1738, 1671, 1349, 1157.

As the paragraph descriping shows that 5264-35-7 is playing an increasingly important role.

Reference£º
Patent; Sankyo Company, Limited; EP1375482; (2004); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem

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

To a solution of 5-methyl-3,4-dihydro-2H-pyrrole (2.50 g, 30.0 mmol) in CCl4 (100 mL) was added N-chlorosuccinimide (32.00 g, 240 mmol), and the mixture was then heated to reflux for 72 hours. The reaction mixture was cooled to 0¡ã C. The formed precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (100 mL), followed by the addition of sodium methoxide (9.80 g, 180 mmol). The resulting suspension was heated to reflux and stirred for 1.5 h. The solvent was evaporated, and the residue was suspended in ether. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and 2 M HCl (100 mL). The biphasic solution was stirred for 10 min. The organic layer was separated, dried over MgSO4, filtered and evaporated. The crude oil was subjected to chromatography purification on silica gel eluting with EtOAc and Hexanes to afford the title compound (2.5 g, 52percent) as an orange solid. MS (ES+) C6H6ClNO2 requires: 159. found: 160 [M+H]+.

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

Reference£º
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (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.55750-48-6,Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.

55750-48-6, EXAMPLE 9; Method for Preparing a Water-soluble Biotinylation Regent that is Reactive with Sulfhydryls or Amines Biotin-4,7,10-trioxa-1,13-tridecanediamine (1.0 g, 2.2 mmol) was dissolved in 12 mL of saturated aqueous sodium bicarbonate and cooled with ice water. N-methoxycarbonyl-maleimide (4.5 mmol, 0.696 g) was added and the reaction stirred at 0 C. for 10 minutes. A 50 mL quantity of water was added to the reaction and the stirring was continued at room temperature for an additional 15 minutes. The solution was extracted with (4¡Á100 mL) chloroform. The combined chloroform extracts were washed with (2¡Á50 mL) water, dried over anhydrous sodium sulfate, and chloroform removed under vacuum. The product was triturated in 100 mL ether and filtered. The isolated product was dried under vacuum to yield 0.57 g (49%) of the compound 18 as a colorless solid; mp=112-114 C.; 1H NMR (MeOH, delta): 1.46 (m, 2H), 1.6-1.8 (m, 9H), 2.2 (t, 2H), 2.7 (d, 1H), 2.9 (dd, 1H), 3.2-3.3 (m, 4H), 3.5-3.6 (m, 15H), 4.3 (m, 1H), 4.5 (m, 1H), 6.8 (s, 2H); IR (KBr, cm-1): 3280, 2910, 2850, 1760, 1690, 1640, 1110, 940; HRMS: calculated for C24H38N4O7S (M+H) is 527.2539, found 527.2526.

As the paragraph descriping shows that 55750-48-6 is playing an increasingly important role.

Reference£º
Patent; Wilbur, D. Scott; Pathare, Pradip M.; Hamlin, Donald K.; Wan, Feng; US2006/228325; (2006); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem