Heterocyclic Building Blocks-Pyrrolines

50609-01-3,50609-01-3, 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound (9a) (0.89 g, 4.6 mmol), DMAP (0.24 g), and EDCI (1.46 g, 7.6 mmol) were added in sequence to a solution of (6) (1.16 g, 3.8 mmol) in anhydrous THF (100 mL). An excess of triethylamine (5 mL) was added dropwise and the mixture was stirred at room temperature for 8 h. Then the reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with HCl (1 M), brine, saturated NaHCO3 solution and dried over Na2SO4. After filtration and concentration of the organic phase, crude (10) (1.19 g, 65%) was obtained. To a solution of (10) (1.19 g, 2.47 mmol) in methanol (60 mL) was added Pd/C (0.20 g), stirred for 24 h at room temperature under the atmosphere of hydrogen. The mixture was filtered to remove Pd/C, and the residue was purified by column chromatography yielding (17a) (0.92 g, 95%) as a white solid.

50609-01-3 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline 6493749, apyrrolidine compound, is more and more widely used in various fields.

Reference£º
Article; Lu, Wen; Li, Pengfei; Shan, Yuanyuan; Su, Ping; Wang, Jinfeng; Shi, Yaling; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1044 – 1054;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

114676-93-6, (2R,4R)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Compound 10 (0.70 g, 3.48 mmol) and PPh3 (1.37 g, 5.22 mmol) in CH2Cl2 (7 mL) was added DEAD (0.91 mL, 5.22 mmol) at 4 C. [Zhao et al., Eur. J. Med. Chem. 2005, 40, 231]. The resulting mixture was stirred for 10 min and then 4-nitrobenzoic acid (1.62 g, 5.22 mmol) was added. This mixture was allowed to warm up to room temperature and stirred for 16 hours. The reaction mixture was quenched with 2 N NaOH solution and extracted with AcOEt. The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash column chromatography to give Compound 15 (0.885 g, 73%) as a pale yellow solid. Compound 15: 1H NMR (400 MHz, CDCl3): delta 1.38 (d, J=0.4 Hz, 3H), 1.48 (s, 9H), 1.96 (d, J=14.4 Hz, 1H), 2.47 (m, 1H), 3.64-3.83 (m, 2H), 4.11 (m, 1H), 5.55 (m, 1H), 8.21 (d, J=8.0 Hz, 2H), 8.31 (d, J=8.0 Hz, 2H).

114676-93-6, The synthetic route of 114676-93-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tanaka, Fujie; Barbas, Carlos F.; Zhang, Haile; US2007/117986; (2007); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

163457-23-6, 3,3-Difluoropyrrolidine hydrochloride is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5.107 3-{4-[4-(3,3-DIFLUORO-PYRROLIDIN-1-YLMETHYL)-BENZYLOXY]-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE To the stirred mixture of 3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (350 mg, 0.8 mmol) and 3,3-difluoropyrrolidin hydrochloride (136 mg, 0.8 mmol) in DCM (10 mL) was added DIPEA (0.28 ml, 1.6 mmol). The resulting mixture was stirred at room temperature for 22 hrs and the reaction mixture was diluted by DCM (30 mL). The mixture was washed with water (20 mL) and brine (20 mL). Organic layer was dried by MgSO4 and concentrated. The residue was purified by ISCO to give 3-{-4-[4-(3,3-Difluoro-pyrrolidin-1-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione as a white solid (256 mg, 69% yield. HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, 20/80, (CH3CN/0.1% H3PO4), 3.59 min (98.6%); mp: 126-128 C.; 1H NMR (DMSO-d6) delta 1.91-2.04 (m, 1H, CHH), 2.15-2.34 (m, 2H, CH2), 2.35-2.44 (m, 1H, CHH), 2.60 (br. s., 1H, CHH), 2.69 (t, J=7.0 Hz, 2H, CH2), 2.76-3.01 (m, 3H, CHH, CH2), 3.62 (s, 2H, CH2), 4.20-4.32 (m, J=17.6 Hz, 1H, CHH), 4.42 (d, J=17.4 Hz, 1H, CHH), 5.11 (dd, J=5.1, 13.2 Hz, 1H, CHH), 5.23 (s, 2H, CH2), 7.22-7.37 (m, 4H, Ar), 7.39-7.63 (m, 3H, Ar), 10.97 (s, 1H, NH); 13C NMR (DMSO-d6) delta 22.33, 31.16, 34.92, 35.55 (t, JC-F=22.50 Hz), 51.30, 51.56, 58.24, 60.99 (t, JC-F=27.57 Hz), 69.35, 114.97, 115.22, 127.69, 128.62, 129.78, 129.93, 130.38, 133.30, 135.44, 137.63, 153.46, 167.97, 170.95, 172.80; LCMS MH=470; Anal. Calcd for C25H25F2N3O4+0.2H2O: C, 63.47; H, 5.41; N, 8.88; Found: C, 63.41; H, 5.46; N, 8.78., 163457-23-6

The synthetic route of 163457-23-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.186550-13-0,1-Boc-3-Aminopyrrolidine,as a common compound, the synthetic route is as follows.

2-Chloro-5-((6-fluoro-2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)benzoic acid (700 mg,2.00mmol),EDC (770 mg, 4.00 mmol),HOBt (540 mg, 4.00 mmol), DIEA (0.9 mL, 5.00 mmol) and compound 1-Boc-3-aminopyrrolidine (400 mg, 2.08 mmol) were dissolved in anhydrous DMF (20 mL).The reaction was carried out overnight at room temperature under argon gas protection. Stop the reaction,The reaction was diluted with DCM / MeOH (10:1, 60 mL).The organic phase was saturated with sodium bicarbonate (30 mL).Wash with saturated ammonium chloride (30 mL) and saturated brine (30 mL¡Á3).Drying over MgSO 4, EtOAc (EtOAc)Recrystallization from DCM/PE gave a pale yellow solid 890mg.The yield is 85.6%.

186550-13-0, As the paragraph descriping shows that 186550-13-0 is playing an increasingly important role.

Reference£º
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Zhao Hailong; Ji Ming; Zhou Jie; Wang Liyuan; Yao Haiping; Jin Jing; (107 pag.)CN108727343; (2018); A;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

99724-19-3, 3-Boc-Aminopyrrolidine is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a. [1-(6-Amino-5-formyl-pyrimidin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester To a suspension of 4-amino-6-chloro-pyrimidine-5-carbaldehyde (239 mg, 1.52 mmol) in CH3CN (2 mL) was added 3-(tert-butoxycarbonylamino)pyrrolidine (312 mg, 1.67 mmol), followed by DIEA (392.9 mg, 3.04 mmol). The mixture was stirred at 90 C. for 1 h. It was cooled to room temperature and the precipitate was filtered off, washed with CH3CN and dried in vacuo to afford the product as a white solid (290.6 mg, 62.2%). 1H NMR (DMSO-d6) delta 9.92 (s, 1H), 8.58 (br, 1H), 7.95 (s, 1H), 7.68 (br, 1H), 7.22 (d, J=6.16 Hz, 1H), 4.02 (m, 1H), 3.80 (m, 2H), 3.66 (m, 1H), 3.45 (m, 1H), 2.03 (m, 1H), 1.82 (m, 1H), 1.38 (s, 9H); LC/MS (ESI) calcd for C14H22N5O3 (MH)+ 308.2, found 308.3., 99724-19-3

The synthetic route of 99724-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gaul, Michael David; Xu, Guozhang; Baumann, Christian Andrew; US2006/281764; (2006); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

945217-60-7, (3R,4S)-rel-tert-Butyl 3,4-diaminopyrrolidine-1-carboxylate is a pyrrolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,945217-60-7

A vial was charged with 4-(2-(ethoxymethoxy)-6-fluorobenzoyl)benzoic acid (32 mg, 0.099 mmol), Et3N (14 mu, 0.099 mmol) and DMF (1 .0 mL) at room temperature. To this solution was then added HATU (38 mg, 0.099 mmol) and the mixture was stirred for 5 min. This solution was then added to a second vial containing a freshly prepared mixture of tert- butyl (3R,4S)-3,4-diaminopyrrolidine-1 -carboxylate (20 mg, 0.099 mmol) and HCI (4.0 M dioxane solution, 50 mu) in DMF (0.5 mL). The resulting solution was stirred at room temperature for 18 h to give tert-butyl (3R,4R)-3-amino-4-(4-(2-(ethoxymethoxy)-6- fluorobenzoyl)benzamido)pyrrolidine-1 -carboxylate which could be directly used in situ. To this solution was added isonicotinic acid (12 mg, 0.099 mmol), Et3N (42 mu, 0.298 mmol) and HATU (38 mg, 0.099 mmol). The mixture was stirred at room temperature for 1 h, then quenched with water and extracted with EtOAc. The organic portion was concentrated in vacuo and then redissolved in THF (1 .0 mL) and aqueous HCI (1 .0 M, 0.5 mL). The solution was warmed to 65C and stirred until the carbamate and acetal protecting groups were fully removed by LCMS. The solution was then purified via HPLC to give N-((3R,4R)-4-(4-(2- fluoro-6-hydroxybenzoyl)benzamido)pyrrolidin-3-yl)isonicotinamide as a formate salt. 1 H NMR (500 MHz, Methanol-^) delta 8.78 – 8.69 (m, 2H), 8.50 (s, 1 H), 7.97 (d, J = 7.3 Hz, 2H), 7.91 (d, J = 7.8 Hz, 2H), 7.82 (d, J = 4.5 Hz, 2H), 7.39 (d, J = 8.0 Hz, 1 H), 6.82 – 6.76 (m, 1 H), 6.72 (t, J = 9.0 Hz, 1 H), 4.73 – 4.65 (m, 2H), 3.75 (d, J = 1 1 .1 Hz, 2H), 3.32 (s, 2H). LCMS (ESI+) for C24H21 FN4O4 [M+H] expected = 449.16, found = 449.26.

The synthetic route of 945217-60-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF MIAMI; AL-ALI, Hassan; LEMMON, Vance; BIXBY, John; (103 pag.)WO2019/89729; (2019); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.383127-22-8,2-(4-Bromophenyl)pyrrolidine,as a common compound, the synthetic route is as follows.

A mixture of 2-(4-bromophenyl)pyrrolidine (50.0 mg, 221 pmol, 1.00 equiv), di-/er/- butyl dicarbonate (57.9 mg, 265 pmol, 1.20 equiv) and dimethylaminopyridine (2.70 mg, 22.1 pmol, 0.10 equiv) in tetrahydrofuran (1.00 mL) was purged with nitrogen and then was stirred at 25 C for 2 h. The mixture was filtered and concentrated under reduced pressure. The resultant residue was purified by prep-TLC (Si02, petroleum ether/ethyl acetate = 10/1) to afford tert- butyl 2-(4-bromophenyl)pyrrolidine-l-carboxylate (55.0 mg, 163 pmol, 73.6% yield, 96.5% purity) as a yellow oil. LC-MS [M-55]: 272.1.

383127-22-8, As the paragraph descriping shows that 383127-22-8 is playing an increasingly important role.

Reference£º
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyrrolidine – Wikipedia
Pyrrolidine | C4H9N – PubChem