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Chemical Structure| 864262-97-5 Chemical Structure| 864262-97-5

Structure of 864262-97-5

Chemical Structure| 864262-97-5

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Product Citations

Product Citations

Li, Kaixuan ; Wang, Mingqian ; Akoglu, Melike ; Pollard, Alyssa C. ; Klecker, John B. ; Alfonso, Patricia , et al.

Abstract: Bruton′s tyrosine kinase (BTK) is a target for treating B-cell malignancies and autoimmune diseases. To aid in the discovery and development of BTK inhibitors and improve clin. diagnoses, we have developed a positron emission tomog. (PET) radiotracer based on a selective BTK inhibitor, remibrutinib. [18F]PTBTK3 is an aromatic, 18F-labeled tracer that was synthesized in 3 steps with a 14.8 ± 2.4% decay-corrected radiochem. yield and ≥99% radiochem. purity. The cellular uptake of [18F]PTBTK3 was blocked up to 97% in JeKo-1 cells using remibrutinib or non-radioactive PTBTK3. [18F]PTBTK3 exhibited renal and hepatobiliary clearance in NOD SCID (non-obese diabetic/ severe combined immunodeficiency) mice, and the tumor uptake of [18F]PTBTK3 in BTK-pos. JeKo-1 xenografts (1.23 ± 0.30% ID/cc) was significantly greater at 60 min post injection compared to the tumor uptake in BTK-neg. U87MG xenografts (0.41 ± 0.11% ID/cc). In the JeKo-1 xenografts, tumor uptake was blocked up to 62% by remibrutinib, indicating the BTK-dependent uptake of [18F]PTBTK3 in tumors.

Keywords: PET imaging ; BTK ; tumor ; fluorine-18 ; Jeko-1 ; U87MG

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Product Details of [ 864262-97-5 ]

CAS No. :864262-97-5
Formula : C12H15BrFNO2
M.W : 304.16
SMILES Code : O=C(OC(C)(C)C)NCC1=CC=C(Br)C=C1F
MDL No. :MFCD08703144

Safety of [ 864262-97-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 864262-97-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 864262-97-5 ]

[ 864262-97-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 24424-99-5 ]
  • [ 112734-22-2 ]
  • [ 864262-97-5 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; In dichloromethane; at 20℃; for 72h;Cooling with ice; To a solution of <strong>[112734-22-2]4-bromo-2-fluorobenzylamine</strong> (1.0 g, 4.9 mmol) and triethylamine (743 mg, 7.4 mmol) in dichloromethane (30 mL) under ice bath conditions was added di-tert-butyl dicarbonate. Esters (1.1 g, 5.1 mmol).After stirring at room temperature for 3 days, the reaction solution was directly concentrated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10/1) to obtain N-Boc-<strong>[112734-22-2]4-bromo-2-fluorobenzylamine</strong> (1.4 g, yield: 94%) is a colorless oily liquid
71% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Product distribution / selectivity; To a solution of (4-bromo-2-fluorophenyl) methanamine (2.5 g, 12 mmol) in DCM (50 mL) at 0 C was added di-terf-butyl dicarbonate (4.01 g, 18 mmol) and triethylamine (2.6 mL, 18 mmol). The mixture was allowed to warm to room temperature and stirred for 2h. Water was added (50 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuum. The crude product was purified by flash silica column chromatography (heptane:ethyl acetate) (1 :0 to 4:1 ) to afford the title compound as a colorless oil. (2.7 g, 71 %).1 H NMR (400 MHz, DMSO-d6) delta ppm 7.21 -7.26 (m, 3 H), 4.90 (br s, H), 4.27-4.33 (m, 2 H), 1 .44 (s, 9 H).
71% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; To a solution of (4-bromo-2-fluorophenyl) methanamine (2.5 g, 12 mmol) in CH2Cl2 (50 mL) at 0 C was added di-tert-butyl dicarbonate (4.01 g, 18 mmol) and triethylamine (2.6 mL, 18 mmol). The mixture was allowed to warm to room temperature and stirred for 2h. Water was added (50 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash silica column chromatography (heptane:ethyl acetate) (1:0 to 4:1) to afford the title compound as a colorless oil. (2.7 g, 71%). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.21-7.26 (m, 3 H), 4.90 (br s, H), 4.27-4.33 (m, 2 H), 1.44 (s, 9 H).
With dmap; triethylamine; In dichloromethane; at 15℃; for 12h; Boc20 (106.96 mg, 490.10 muiotaetaomicron) and DMAP (5.99 mg, 49.01 muiotaetaomicron) were added to a solution of Compound BD2-2 (100.00 mg, 490.10 muiotaetaomicron) and TEA (148.78 mg, 1.47 mmol) in DCM (4.00 mL). The mixture was stirred at 15C for 12 hours. LCMS showed the reaction was completed. The mixture was concentrated to get crude residue. The residue was purified by prepatory-TLC (S1O2, Petroleum ether:Ethyl acetate mixture with a ratio of 5: 1) to afford Compound BD2-3 (90.00 mg, crude) as a yellow oil.

 

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