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Chemical Structure| 1094544-66-7 Chemical Structure| 1094544-66-7

Structure of 1094544-66-7

Chemical Structure| 1094544-66-7

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Product Details of [ 1094544-66-7 ]

CAS No. :1094544-66-7
Formula : C10H15NO
M.W : 165.23
SMILES Code : NC1=CC=C(OC(C)C)C(C)=C1
MDL No. :MFCD11214161

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Application In Synthesis of [ 1094544-66-7 ]

* 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 [ 1094544-66-7 ]

[ 1094544-66-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1171919-75-7 ]
  • [ 1094544-66-7 ]
  • tert-butyl (3R)-3-[(2-sulfanylacetyl)amino]piperidine-1-carboxylate [ No CAS ]
  • (R)-tert-butyl 3-(3-amino-4-((4-isopropoxy-3-methylphenyl)amino)thieno[2,3-b]pyridine-2-carboxamido)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% To a microwave vial containing a stir bar were added <strong>[1171919-75-7]2-chloro-4-iodonicotinonitrile</strong> (1441 mg, 5.449 mmol), 4-isopropoxy-3- methylaniline (907 mg, 5.49 mmol), DPEPhos (144 mg, 0.268 mmol), Pd(OAc)2(58.0 mg, 0.258 mmol), and CS2CO3(1775 mg, 5.448 mmol). To the vial was added with dioxane (10 mL) via syringe and the mixture was degassed under a vacuum for 1 minute, then vented to nitrogen. The reaction was heated in the microwave at 150 C for 30 minutes. The reaction was cooled to room temperature, treated with (R)-tert-buty 3-(2-mercaptoacetamido)piperidine-1-carboxylate (Intermediate 22) (0.49 M in dioxane, 10 mL, 4.9 mmol) via syringe, evacuated and flushed with nitrogen, and stirred at 150 C for 20 min. The reaction was then cooled to room temperature. The reaction mixture was treated with solid CDI (2230 mg, 13.75 mmol) in one portion under air, resealed, evacuated and flushed with nitrogen, and stirred at 150 C for 20 min. The CDI reaction did not go, so the intermediate was purified. The reaction was then diluted with EtOAc (100 mL) and saturated aqueous sodium bicarbonate (100 mL) and separated. The aqueous layer was extracted again with EtOAc (100 mL), and the combined organics were dried over anhydrous MgSC>4, concentrated to dryness, and purified by flash column chromatography to yield the title compound (558 mg, 19.0% yield). MS (ESI): mass calcd. for C28H37N5O4S, 539.70; m/z found, 540.2 [M+H]+.
 

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