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Chemical Structure| 933784-97-5 Chemical Structure| 933784-97-5

Structure of 933784-97-5

Chemical Structure| 933784-97-5

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Product Details of [ 933784-97-5 ]

CAS No. :933784-97-5
Formula : C13H16FN5O
M.W : 277.30
SMILES Code : NC1=NC=C(F)C(C2=CN=C(C)N2C3CCOCC3)=N1

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Application In Synthesis of [ 933784-97-5 ]

* 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 [ 933784-97-5 ]

[ 933784-97-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 933784-97-5 ]
  • [ 837-12-7 ]
  • 5-fluoro-N-{4-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-4-[2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl]pyrimidin-2-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% General Method DDl (1.0 equiv.), D2 (0.85-1.24 equiv.) and sodium tert-butoxide (1.34-1.46 equiv.) were mixed in 1,4-dioxane and the mixture was flushed with argon for 5-10 minutes before Pd(OAc)2 (0.04-0.082 equiv.) and Pd(^-Bu3P)2 (0.044-0.06 equiv.) were added. The mixture was flushed with argon then heated in a sealed tube at +110-+ 120 C until the reaction was complete (as monitored by TLC or LC-MS). If the reaction was not complete after 24 h more Pd(OAc)2, Pd(t-Bu3P)2 and sodium tert-butoxide were added. The solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and water. After extraction the organic layer was dried (Na2SO4), filtered and evaporated. The crude of the free base was purified using preparative HPLC. MeCN was evaporated in vacuo and the aqueous phase was extracted with CH2Cl2. The organic phase was washed with water at pH 9 (diluted NaHCO3 solution), dried (Na2SO4), filtered and evaporated. The residue was dissolved in CH2Cl2 and the HCl-adduct of the product was precipitated from the solution by addition of 0.1M HCl in ether (1-5 equiv. HCl). The solvent was evaporated and the residue was dissolved in water and freeze dried.Example 7(f) 5-Fluoro-N-{4-[(4-methylpiperazin-l-yl)sulfonyl]phenyl}-4-[2-methyl-l- (tetrahydro-2H-pyran-4-yl)-lH-imidazol-5-yl]pyrimidin-2-amine hydrochlorideThe title compound was prepared in accordance with the general method D, with the exception that the base of the product was purified by flash chromatography(CHCl3/Me0H/NH3 aq. 200:10:1) before purification by preparative HPLC. Using 5- fluoro-4-[2-methyl-l-(tetrahydro-2H-pyran-4-yl)-lH'-imidazol-5-yl]pyrimidm-2 -amine (0.075 g, 0.27 mmol, obtained from Example 7(e)), l-(4-bromo-benzenesulfonyl)-4- methylpiperazine (described in WO 2003004472) (0.108 g, 0.338 mmol), sodium tert- butoxide (0.036 g, 0.38 mmol), Pd(OAc)2 (0.012 g, 0.054 mmol) and Pd(^-Bu3P)2 (0.14 g, 0.027 mmol), the title compound (0.018 g, 11%) was obtained as a yellow solid. 1H NMR (DMSO-rf* 300 MHz) δ 10.64 (br s, 1 H), 10.43 (s, 1 H), 8.90 (s, 1 H), 8.07 (s, 1 H), 7.96 (d, J= 8.4 Hz, 2 H), 7.70 (d, J= 8.4 Hz, 2 H), 5.03-4.93 (m, 1 H), 3.90-3.70 (m, 4 H), 3.36-3.15 (m, 4 H), 2.81 (s, 3 H), 2.74 (s, 3 H), 2.25-2.15 (m, 2 H), 2.00-1.92 (m, 2 H); MS (ESI) m/z 516 (M+l).
 

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