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[ CAS No. 1300737-69-2 ] {[proInfo.proName]}

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Chemical Structure| 1300737-69-2
Chemical Structure| 1300737-69-2
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CAS No. :1300737-69-2 MDL No. :
Formula : C23H23N5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 417.46 Pubchem ID :-
Synonyms :

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* 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.

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[ 1300737-69-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1300737-69-2 ]
  • [ 1300031-49-5 ]
YieldReaction ConditionsOperation in experiment
77% With [bis(acetoxy)iodo]benzene; potassium hydroxide In methanol for 1.33333 h; Cooling with ice 7-(3,5-Dimethyl-4-isoxazolyl)-6-(methyloxy)-4-[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide (45 g, 102 mmol) was dissolved in methanol (500 mL) and potassium hydroxide (7.47 g, 133 mmol) was added. The mixture was stirred in an ice bath, then iodobenzene diacetate (39.6 g, 123 mmol) was added in small portions over 20 min and the mixture stirred for a further 1 h. The solvent was evaporated in vacuo, the residue diluted with water (1 L), and the resulting gummy suspension extracted with DCM (2 x 300 mL). The solvent was dried (sodium sulphate) and loaded directly onto a silica column (750 g), which was then eluted with a 2M ammonia in methanol / DCM gradient (0-10percent). After evaporation of solvents in vacuo 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (32.7 g, 77percent yield) was obtained as a beige solid. 1H-NMR (600 MHz, DMSO-d6) d ppm 2.03 (d, J=6.5 Hz, 3 H), 2.04 (s, 3 H), 2.25 (s, 3 H), 3.46 (bs, 3 H), 6.26 (q, J=7.1 Hz, 1 H), 6.69 (bs, 1 H), 7.35 (dd, J=7.0, 5.1 Hz, 1 H), 7.41 (d, J=6.6 Hz, 1 H), 7.76-7.79 (m, 1 H), 7.79 (s, 1 H), 8.59-8.65 (m, 2 H), 11.77 (bs, 1H). 13C NMR (151 MHz, DMSO-d6) d ppm 10.3, 11.3, 17.6, 51.8, 55.5, 100.8, 112.0, 115.4, 120.2, 121.0, 122.7, 122.7, 128.1, 132.3, 132. 8, 137.6, 139.8, 149.3, 154.3, 154.5, 159.0, 159.2, 166.0. MS (Method HpH): MH+ 416, Rt 0.85 min. HRMS (m/z): [MH]+ calcd for C23H22N5O3 416.1723; found 416.1718.
33% With [bis-(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; The carboxamide intermediate (6 g) was treated with an excess of [bis(trifluoroacetoxy)iodo]benzene (19.35 g, 45 mmol) in CH3CN (100 ml), the mixture was stirred at room temperature overnignt.
The reaction mixture was concentrated in vacuo, the resulting residue was dissolved in DCM and washed with water.
The crude product was purified by flash chromatography on silica gel (DCM/MeOH, 95:5), the resulting compound was dissolved in DCM and precipitated from diethylether to give the title compound as an off-white powder (2.5 g, 33percent)
LC-HRMS ES+ exact mass calculated for C23H21N5O3: 416.1722 MH+.
Found 416.1736, Rt=2.22 min. (APCI-MS) m/z 415.97 MH+, Rt 2.5 min.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2963 - 2967
[2] Patent: US2012/232074, 2012, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2011/54846, 2011, A1, . Location in patent: Page/Page column 84
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