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Chemical Structure| 16814-08-7 Chemical Structure| 16814-08-7

Structure of 16814-08-7

Chemical Structure| 16814-08-7

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Product Details of [ 16814-08-7 ]

CAS No. :16814-08-7
Formula : C11H18NO3P
M.W : 243.24
SMILES Code : NC(P(OCC)(OCC)=O)C1=CC=CC=C1
MDL No. :N/A

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Application In Synthesis of [ 16814-08-7 ]

* 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 [ 16814-08-7 ]

[ 16814-08-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 16814-08-7 ]
  • [ 17823-69-7 ]
  • [ 1038997-47-5 ]
  • 2
  • [ 16814-08-7 ]
  • [ 56844-12-3 ]
  • [ 1610772-07-0 ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine; In 1,4-dioxane; at 100℃; for 24h;Sealed tube; Step 3: Displacement of the C-4 chloro of intermediate 14 (Scheme 4) with diethyl diethyl (amino(phenyl)methyl)phosphonate via an SNAr reaction under the same conditions as previously described for the conversion of intermediate 14 to 15 (Scheme 4) gave the diethyl (((6-bromothieno[2.3- djpyrimidin-4-yl)amino)(phenyl)methyl)phosphonate intermediateTo a pressure vessel, 6-bromo-4-chlorothieno[2,3-djpynmidine (13) (70 mg, 0.28 1 mmol, leq.) and diethyl (amino(phenyl)methyl)phosphonate (136.5 mg, 0.561 mmol, 2eq.) was dissolved in dioxane. Triethylamine (0.196 mL, 1.403 mmol, Seq.) was added dropwise to the reaction and the pressure vessel was sealed and stirred at 100C for 24 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (10 mL). The organic layer was washed with saturated sodium bicarbonate solution (5 mL), water (10 mL), brine (10 mL) and dried over Mg504. The product was purified by column chromatography (0% to 100% ethyl acetate/hexanes and 0% to 20% methanol/ethyl acetate) to give the desired product as a white solid in 36% yield (51 mg).?H NMR (300 MHz, CDC13) 8.42 (s, 1H), 8.11-8.07 (m, 1H), 7.70-7.67 (m, 3H), 7.27-7.22 (m, 2H),6.32 (dd, J= 22.4, 9.6 Hz, 1H), 4.31-4.07 (m, 3H), 3.93-3.84 (m, 1H), 1.28-1.19 (s, 6H). ?3C NMR(75 MHz, CDC13) 167.7, 155.0 (d, J = 9 Hz), 153.7, 128.49 (d, J = 2 Hz), 128.44 (d, J = 2 Hz), 127.99 (d, J 3 Hz), 121.7, 117.8, 111.3, 63.5 (d, J 7 Hz), 50.79 (d, J 156 Hz), 16.3 (dd, J 19, 6 Hz). MS (ESI+) calculated for C,7H20BrN3O3PS m/z [M + Hib: 456.01, found m/z 456.14After Suzuki cross-coupling reaction, followed by ester hydrolysis following the general protocols described before inhibitors such as Examples 36-1 and 37-1 were obtained.
 

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