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Azetidines

Azetidines are a class of four-membered heterocyclic compounds containing a single nitrogen atom.
These versatile molecules have diverse applications in organic synthesis and medicinal chemistry.
Their unique structural features and reactivity make them valuable building blocks for the preparation of various nitrogen-containing compounds.
Azetidines exhibit a wide range of biological activities and have been explored for their potential therapeutic properties, such as in the development of novel pharmaceuticals.
Researchers in the field of Azetidines can leverage PubCompare.ai's AI-driven platform to optimise their research protocols, effortlessly locate the best protocols from literature, pre-prints, and patents, and identify the most effective products, streamlining their research process.
Experienec the future of Azetidines research today with PubCompare.ai.

Most cited protocols related to «Azetidines»

Ruthenium-Catalyzed Azetidine Synthesis

Cited 2 times

A screwcap pressure vessel, equipped with a magnetic stir bar, was charged with 1–5 (50 mg, 0.21 mmol) RuPhos (1 mg, 1 mol %) and RuPhos precatalyst (P1) (1.75 mg, 1 mol %). The vial was evacuated and backfilled with argon, and sealed with a Teflon screw cap. LiHMDS (1 M in THF, 2.4 equiv) was added via syringe, followed by azetidine (0.25 mmol, 1.2 equiv). The reaction mixture was heated at 90 °C for 96 h. Conversion for the reaction was low. The solution was allowed to cool to room temperature, and then quenched by the addition of 1 M HCl (1 mL), diluted with EtOAc and poured into sat. NaHCO₃. After being extracted with EtOAc, the combined organic layers were washed with brine, dried over MgSO₄, then concentrated and purified by flash column chromatography using MeOH/DCM (10/90) as eluent to afford compound 1–6a (6.5 mg, 31% based on 32 mg (64%), recovered starting material) as white solid. ¹H NMR (600 MHz, CDCl₃): δ 7.98 (m, 1H), 7.90 (d, 1H, J = 9 Hz), 7.30 (m,1 H), 6.94 (m,1 H), 6.89 (d, 1H, J = 8.4 Hz), 4.38 (t, 4 H, J = 7.2 Hz), 3.90 (s, H), 2.52 (m, 2 H); ¹³C NMR (150 MHz, DMSO-d₆): δ 159.83, 149.05, 141.87, 136.84, 128.30, 123.52, 122.33, 115.48, 109.56, 106.39, 95.22, 55.61, 51.82, 17.42; HRMS (ESI): m/z [M + H]+ calcd for C₁₅H₁₆N₃O⁺: 254.1288, found: 254.1284; purity > 95%.

Kumar K., Wang P., Sanchez R., Swartz E.A., Stewart A.F, & DeVita R.J. (2018). Development of Kinase-Selective, Harmine-Based DYRK1A Inhibitors that Induce Pancreatic Human β-Cell Proliferation. Journal of medicinal chemistry, 61(17), 7687-7699.

Publication 2018

1H NMR Argon Azetidines Bicarbonate, Sodium Blood Vessel brine Carbon-13 Magnetic Resonance Spectroscopy Chromatography Conversion Disorder Pressure Sulfate, Magnesium Sulfoxide, Dimethyl Syringes Teflon

Synthesis of Primary Alcohol from Azetidine

Cited 2 times

Azetidine 6a (14.1 g, 19.09 mmol, 1.0 equiv) was dissolved in CH₂Cl₂ (191 mL) and cooled to 0 °C. Trifluoroacetic acid (14.9 ml, 191 mmol, 10 equiv) was then added over approximately 10 min until the yellow color persisted. The mixture was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate and the aqueous layer extracted 2 additional times with CH₂Cl₂. The combined organic extracts were dried over MgSO₄, filtered and concentrated under reduced pressure to provide the crude product, which was purified by chromatography over silica gel using hexanes/EtOAc to provide the primary alcohol 7a (8.74 g, 92%) as a foam.

{[α]}_{D}^{20} = - 46.2

(c 0.59, CHCl₃); IR ν_max (film): 3335, 2873, 1538, 1346, 1166, 905; ¹H NMR (500 MHz, CDCl₃) δ 7.83 (dd, J = 7.8, 1.4 Hz, 1H), 7.79 (dd, J = 7.9, 1.3 Hz, 1H), 7.72 (td, J = 7.7, 1.5 Hz, 1H), 7.66 (td, J = 7.6, 1.3 Hz, 1H), 7.22 (m, 4H), 5.83 (m, 1H), 5.28 (d, J = 17.1 Hz, 1H), 5.17 (d, J = 10.1 Hz, 1H), 4.92 (s, 1H), 3.64 (s, 1H), 3.54 (s, 2H), 3.49–3.42 (m, 1H), 3.37 (m, 1H), 3.21 (s, 3H), 2.92 (t, J = 10.3 Hz, 1H); ¹³C NMR (125 MHz, CDCl₃) δ 147.6, 135.5, 133.8, 133.5, 132.7, 132.6, 132.2, 131.2, 130.9, 125.7, 121.4, 118.6, 67.3, 64.8, 61.4, 61.1, 42.8, 41.8; HRMS (ESI) calcd for C₂₀H₂₃BrN₃O₅S [M + H]⁺: 496.0542, found: 496.0545.

Lowe J.T., Lee MD I.V., Akella L.B., Davoine E., Donckele E.J., Durak L., Duvall J.R., Gerard B., Holson E.B., Joliton A., Kesavan S., Lemercier B.C., Liu H., Marié J.C., Mulrooney C.A., Muncipinto G., Welzel-O’Shea M., Panko L.M., Rowley A., Suh B.C., Thomas M., Wagner F.F., Wei J., Foley M.A, & Marcaurelle L.A. (2012). Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-Like Libraries. The Journal of organic chemistry, 77(17), 7187-7211.

Publication 2012

1H NMR Azetidines Bicarbonate, Sodium Carbon-13 Magnetic Resonance Spectroscopy Chloroform Chromatography Ethanol Hexanes Pressure quinoline yellow Silica Gel Sulfate, Magnesium Trifluoroacetic Acid

Synthesis of Nicotinate Derivative

Cited 1 time

Ethyl 6-chloro-5-cyano-2-methylnicotinate (1; 0.33 g, 1.49 mmol) and 3-(Boc-amino)-azetidine (0.31 g, 1.80 mmol) were dissolved in 1,2-dichloroethane (4 mL) and N,N-diisopropylethylamine (DiPEA; 0.6 mL, 3.4 mmol) was added. After stirring at 60 °C for 1 h, the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (EtOAc; 10 mL) and washed twice with saturated aqueous NaHCO₃ (8 mL). The organic layer was dried over Na₂SO₄ and concentrated in vacuo. Flash column chromatography (EtOAc/n-hexane 1:6) was performed to obtain ethyl 6-(3-((tert-butoxycarbonyl)amino)azetidin-1-yl)-5-cyano-2-methylnicotinate (2) in 32% yield (0.17 g, 0.47 mmol).
R_f value: 0.14 (EtOAc/n-hexane 1:6), 0.64 (CH₂Cl₂/MeOH 95:5); ¹H NMR (250.13 MHz, CDCl₃) δ 8.27 (s, 1H, CH_Ar), 5.28-5.33 (m, 1H, CH_azetidine), 4.68-4.75 (m, 2H, CH_{2 (azetidine)}), 4.31 (q, 2H, J = 7.1 Hz, CH_{2 (ester)}), 4.21-4.27 (m, 2H, CH_{2 (azetidine)}), 2.71 (s, 3H, CH_{3 (pyridine)}), 1.48 (s, 9H, 3x CH₃), 1.39 (t, 3H, J = 7.1 Hz, CH_{3 (ester)}); ¹³C NMR (125.80 MHz, CDCl₃) δ 208.68, 165.38, 164.86, 161.23, 164.86, 146.20, 117.17, 104.83, 86.65, 60.89, 59.25, 41.40, 28.29, 25.72, 14.29; ESI-HRMS: calculated for C₁₈H₂₄N₄O₄: 360.18; found 383.1712 [M+Na]⁺.

Villa A., Klein B., Janssen B., Pedragosa J., Pepe G., Zinnhardt B., Vugts D.J., Gelosa P., Sironi L., Beaino W., Damont A., Dollé F., Jego B., Winkeler A., Ory D., Solin O., Vercouillie J., Funke U., Laner-Plamberger S., Blomster L.V., Christophersen P., Vegeto E., Aigner L., Jacobs A., Planas A.M., Maggi A, & Windhorst A.D. (2018). Identification of new molecular targets for PET imaging of the microglial anti-inflammatory activation state. Theranostics, 8(19), 5400-5418.

Publication 2018

1H NMR Azetidines Bicarbonate, Sodium Carbon-13 Magnetic Resonance Spectroscopy Chromatography DIPEA Esters ethyl acetate Ethylene Dichlorides methylnicotinate n-hexane pyridine Salvelinus TERT protein, human

Synthesis of 4-Fluorobenzylideneazetidine

Cited 1 time

To a solution of 4-fluorobenzaldehyde (2.00 g, 16.1 mmol) in DMSO (80.5 mL) was added anhydrous K₂CO₃ (6.66 g, 3.0 eq) followed by the addition of azetidine hydrochloride (2.24 g, 24.0 mmol, 1.50 eq) with stirring at 110 °C overnight. The mixture was then cooled to room temperature, diluted with water (200 mL), and extracted with ethyl acetate (3 × 100 mL). The organic layer was washed with brine (50 mL) and dried over sodium sulfate, then concentrated in vacuo. Purification by flash chromatography (20% ethyl acetate/hexanes) afforded 5 as a pale yellow solid (1.81 g, 70% yield). ¹H-NMR (500 MHz, CDCl₃): δ 9.76 (s, 1H), 7.74 (d, J = 8.6 Hz, 2H), 6.46 (d, J = 8.2 Hz, 2H), 4.08 (t, J = 7.4 Hz, 4H), 2.60 – 2.37 (m, 2H). LCMS: 162.1 (M+H).

Mofford D.M., Liebmann K.L., Sankaran G.S., Reddy G.S., Reddy G.R, & Miller S.C. (2017). Luciferase activity of insect fatty acyl-CoA synthetases with synthetic luciferins. ACS chemical biology, 12(12), 2946-2951.

Publication 2017

1H NMR Azetidines brine Chromatography ethyl acetate Hexanes Lincomycin potassium carbonate sodium sulfate Sulfoxide, Dimethyl

Synthesis and Characterization of Sazetidine-A

Cited 1 time

Sazetidine-A (6-(5-(S)-azetidin-2-yl)methoxypyridine-3-yl)hex-5-yn-1-ol) was synthesized according to published methods (Kozikowski et al. 2009 (link)). Mecamylamine hydrochloride, methyllycaconitine citrate hydrate (MLA), dihydro-beta-erythroidine hydrobromide (DHβE), and desipramine hydrochloride were purchased from Sigma (St. Louis, MO), sertraline hydrochloride from Toronto Research Chemicals (Ontario, Canada), varenicline tartrate from Allichem (Savage, MD) and 5-Iodo-A-85380 (5-I-A85380) dihydrochloride from Tocris Bioscience (Ellisville, MO). All drugs were dissolved in either saline, phosphate buffered saline, or injectable water and injected intraperitoneally (i.p) in a volume of 10 ml/kg. All doses are expressed as salt except for varenicline, which is expressed as the freebase.

Caldarone B.J., Wang D., Paterson N.E., Manzano M., Fedolak A., Cavino K., Kwan M., Hanania T., Chellappan S.K., Kozikowski A.P., Olivier B., Picciotto M.R, & Ghavami A. (2011). Dissociation between duration of action in the forced swim test and nicotinic acetylcholine receptor occupancy with sazetidine, varenicline, and 5-I-A85380. Psychopharmacology, 217(2), 199-210.

Publication 2011

Azetidines beta-erythroidine hydrobromide Citrates Hydrochloride, Desipramine Iodine Mecamylamine methyllycaconitine Pharmaceutical Preparations Phosphates Saline Solution Sertraline Hydrochloride Sodium Chloride Varenicline Varenicline Tartrate

Most recents protocols related to «Azetidines»

Synthesis of Quinoline-4-Carboxylic Acid Derivative

Not available on PMC !

Example 182

[Figure (not displayed)]

6-(3-Fluoro-3-phenylazetidin-1-yl)quinoline-4-carboxylic acid Intermediate 343 (22 mg, 0.07 mmol), HATU (39 mg, 0.10 mmol) and DIPEA (48 μL, 0.27 mmol) were mixed in MeCN (1 mL) and EtOAc (1 mL). (R)-3-Glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (17 mg, 0.08 mmol) was added and the reaction mixture was stirred at rt for 1 h. DCM (8 mL) and NaHCO₃(5 mL, aq) were added, and the reaction mixture was stirred, filtered through a phase separator and evaporated under reduced pressure. The crude compound was purified by preparative SFC, PrepMethod SFC-E, (gradient: 30-35%), to give the title compound (2.4 mg, 7%); HRMS (ESI) m/z [M+H]⁺ calcd for C₂₅H₂₃FN₅O₂S: 476.1550, found: 476.1560.

US11858924B2. N-(2-(4-cyanothiazolidin-3-yl)-2-oxoethyl)-quinoline-4-carboxamides (2024-01-02). AstraZeneca AB [SE]. Inventors: Jonas Brånalt [SE], Maria Johansson [SE], Anneli Nordqvist [SE], Marianne Swanson [SE].

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Patent 2024

Azetidines Bicarbonate, Sodium DIPEA Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid

Synthesis of Novel Quinoline-Thiazolidine Compound

Not available on PMC !

Example 187

[Figure (not displayed)]

6-(3-(4-Chlorobenzyl)azetidin-1-yl)quinoline-4-carboxylic acid Intermediate 353 (80 mg, 0.23 mmol), HATU (129 mg, 0.34 mmol) and DIPEA (158 μL, 0.91 mmol) were mixed in MeCN (2 mL) and EtOAc (2 mL). (R)-3-Glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (56 mg, 0.27 mmol) was added and the reaction mixture was stirred at rt for 3 h. DCM (15 mL) and NaHCO₃(15 mL, aq) were added, and the reaction mixture was stirred, filtered through a phase separator and evaporated under reduced pressure. The crude compound was purified by preparative HPLC, PrepMethod F, (gradient 5-95%) to give the title compound (18 mg, 16%); HRMS (ESI) m/z [M+H]⁺ calcd for C₂₆H₂₅C₁N₅O₂S: 506.1412, found: 506.1428; ¹H NMR (600 MHz, DMSO-d₆) δ 8.89 (t, 1H), 8.57 (d, 1H), 7.82 (d, 1H), 7.36 (d, 1H), 7.33-7.29 (m, 2H), 7.25 (d, 2H), 7.11-7.03 (m, 2H), 5.27-5.21 (m, 1H), 4.82 (d, 1H), 4.66 (d, 1H), 4.24 (d, 2H), 3.99 (q, 2H), 3.66-3.59 (m, 2H), 3.35-3.28 (m, 2H), 2.99 (dt, 1H), 2.90 (d, 2H).

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Patent 2024

1H NMR Azetidines Bicarbonate, Sodium DIPEA High-Performance Liquid Chromatographies Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid Sulfoxide, Dimethyl

Synthesis of a Quinoline-Thiazolidine Conjugate

Not available on PMC !

Example 137

[Figure (not displayed)]

DIPEA (372 μL, 2.13 mmol) was added to a stirred suspension of 6-(3-ethyl-3-methylazetidin-1-yl)quinoline-4-carboxylic acid Intermediate 262 (115 mg, 0.43 mmol), (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (177 mg, 0.85 mmol), HOBt (172 mg, 1.28 mmol) and EDC (245 mg, 1.28 mmol) in MeCN (6 mL) and EtOAc (6 mL) at 20° C., and the reaction mixture was stirred at 50° C. for 2 h. The solvent was removed under reduced pressure, and the residue was dissolved in NaHCO₃(30 mL, aq) and EtOAc (80 mL). The phases were separated and the aqueous layer was extracted with EtOAc (4×75 mL). The combined organic layer was washed with water (3×50 mL), dried over Na₂SO₄, filtered and evaporated at reduced pressure. The crude product was purified by preparative HPLC, PrepMethod I, (gradient: 60-78%) to give the title compound (0.110 g, 61%) as a yellow solid; HRMS (ESI) m/z [M+H]⁺ calcd for C₂₂H₂₆N₅O₂S: 424.1802 found: 424.1802; ¹H NMR (400 MHz, DMSO-d₆) δ 9.02-8.90 (m, 1H), 8.61 (d, 1H), 7.87 (d, 1H), 7.39 (d, 1H), 7.17 (d, 1H), 7.10 (dd, 1H), 5.32 (dd, 1H), 4.89 (d, 1H), 4.71 (d, 1H), 4.30 (d, 2H), 3.70 (dd, 2H), 3.62 (d, 2H), 3.43-3.34 (m, overlapping with solvent), 1.63 (q, 2H), 1.27 (s, 3H), 0.90 (t, 3H).

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Patent 2024

1-hydroxybenzotriazole 1H NMR Azetidines Bicarbonate, Sodium DIPEA High-Performance Liquid Chromatographies Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid Solvents Sulfoxide, Dimethyl

Synthesis of Fluorinated Imidazopyridine Derivative

Not available on PMC !

Example 4

[Figure (not displayed)]

To a solution of (S)-2-(6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-indazol-3-yl)-5-propyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid, TFA (30 mg, 0.052 mmol), N,N-dimethylazetidin-3-amine, 2HCl (27.0 mg, 0.156 mmol), and DIPEA (0.064 mL, 0.364 mmol) in DMF (1.5 mL), was added HATU (29.6 mg, 0.078 mmol) and the reaction mixture was stirred at RT overnight. Hydrazine (5 eq) was added, the reaction mixture was stirred at RT for 10 min, concentrated and purified by preparative HPLC to provide the TFA salt of the title compound (29.6 mg, 74% yield). (m/z): [M+H]⁺ calcd for C₃₀H₃₆FN₇O₂546.29 found 546.6.

US11878977B2. JAK inhibitors containing a 4-membered heterocyclic amide (2024-01-23). THERAVANCE BIOPHARMA R&D IP, LLC [US]. Inventors: Paul R. Fatheree [US], Gary E. L. Brandt [US], Cameron Smith [US], Steven D. E. Sullivan [US], Lori Jean Van Orden [US], Melanie A. Kleinschek [US], Glenn D. Crater [US].

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Patent 2024

Amines Azetidines Carboxylic Acids DIPEA High-Performance Liquid Chromatographies hydrazine Indazoles pyridine Sodium Chloride

Synthesis of Novel Quinoline-Thiazolidine Compound

Not available on PMC !

Example 186

[Figure (not displayed)]

6-(3-(m-Tolyl)azetidin-1-yl)quinoline-4-carboxylic acid Intermediate 351 (90 mg, 0.28 mmol), HATU (161 mg, 0.42 mmol) and DIPEA (197 μL, 1.13 mmol) were mixed in MeCN (2 mL) and EtOAc (2 mL). (R)-3-Glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (70 mg, 0.34 mmol) was added and the reaction mixture was stirred at rt for 3 h. DCM (15 mL) and NaHCO₃(15 mL, aq) were added, and the reaction mixture was stirred, filtered through a phase separator and evaporated under reduced pressure. The compound was purified by preparative HPLC, PrepMethod F, (gradient 5-95%) to give the title compound (58 mg, 51%); HRMS (ESI) m/z [M+H]⁺ calcd for C₂₆H₂₆N₅O₂S: 472.1802, found: 472.1792: 471.18; ¹H NMR (600 MHz, DMSO-d₆) δ 8.97 (t, 1H), 8.64 (d, 1H), 7.89 (d, 1H), 7.43 (d, 1H), 7.27 (d, 1H), 7.23-7.12 (m, 4H), 7.03 (d, 1H), 5.28 (dd, 1H), 4.84 (d, 1H), 4.67 (d, 1H), 4.38 (t, 2H), 4.27 (d, 2H), 3.99-3.88 (m, 3H), 3.37-3.26 (m, 2H), 2.27 (s, 3H).

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Patent 2024

1H NMR Azetidines Bicarbonate, Sodium DIPEA High-Performance Liquid Chromatographies Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid Sulfoxide, Dimethyl

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More about "Azetidines"

Azetidines are a fascinating class of four-membered heterocyclic compounds that contain a single nitrogen atom.
These versatile molecules have garnered significant attention in the realms of organic synthesis and medicinal chemistry due to their unique structural features and diverse reactivity.
As a key building block for the preparation of various nitrogen-containing compounds, azetidines have been extensively explored for their potential therapeutic applications.
One of the unique aspects of azetidines is their ability to exhibit a wide range of biological activities, making them a valuable target for drug discovery and development.
Researchers in the field of azetidines can leverage the power of PubCompare.ai's AI-driven platform to optimize their research protocols, effortlessly locate the best protocols from literature, preprints, and patents, and identify the most effective products, streamlining their research process.
In addition to their medicinal applications, azetidines have also found use in the preparation of other important compounds.
For instance, the 21.2×250 mm Luna Axia C18 column, XBridge C18, Gemini C18, Xbridge C18 150, and Lux Cellulose-4 columns have been employed in the analysis and purification of azetidine-containing molecules.
Furthermore, related compounds such as nicotine hydrogen tartrate salt, HPLC-grade acetonitrile, acetylcholine chloride (ACh), and cyclohexane (ACS) have also been utilized in azetidine-related research.
Experienec the future of azetidines research today with PubCompare.ai and unlock the full potential of this versatile class of compounds.
Discover new applications, optimize your research protocols, and stay ahead of the curve in the ever-evolving field of azetidines.