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Chemical Structure| 474417-44-2 Chemical Structure| 474417-44-2

Structure of 474417-44-2

Chemical Structure| 474417-44-2

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Product Details of [ 474417-44-2 ]

CAS No. :474417-44-2
Formula : C10H15N3
M.W : 177.25
SMILES Code : C[C@@H]1CN(C2=NC=CC=C2)CCN1

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Application In Synthesis of [ 474417-44-2 ]

* 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 [ 474417-44-2 ]

[ 474417-44-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 6557-86-4 ]
  • [ 474417-44-2 ]
  • [ 1443748-20-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; General procedure: (R)-4-N-Boc-2-methyl piperazine (490 mg, 2.44 mmol), 2-bromopyridine (257 lL, 2.69 mmol), Xantphos (212 mg, 0.366 mmol), Pd2(dba)3 (112 mg, 0.112 mmol), and NaOtBu(705 mg, 7.34 mmol) were added to 5.0 mL of dioxanes in a microwave reaction vial. The reaction was heated for 10 min in the microwave at 120 C and monitored by LCMS. Upon completion, the mixture was cooled and filtered through a pad of celite and concentrated in vacuo. The crude material was purified by flash chromatography and immediately dissolved in 1.0 mL of MeOH with stirring. 4 N HCl in dioxanes (4.0 mL, 16 mmol) was added. Once the protecting group had cleaved as judged by LCMS, an aqueous solution of saturated sodium bicarbonate was added until the pH was basic. The mixture was extracted with dichloromethane, and the organic layers were concentrated in vacuo to afford 260 mg (60%) of (R)-2-methyl-1-(pyridin-2-yl)piperazine as a colorless liquid. (R)-2-Methyl-1-(pyridin-2-yl)piperazine(260 mg, 1.47 mmol), 1-adamantoyl chloride (437 mg, 2.20 mmol), and DIEA (508 lL, 2.93 mmol) were dissolved in 1.0 mL of dichloromethane and monitored by LCMS. Upon completion, 5.0 mL of MeOH was added, and the mixture was concentrated in vacuo. The crude product was purified via reverse phase chromatography (0.1% TFA in H2O/MeCN). The fractions containing the product were combined and neutralized by the addition of aqueous saturated sodium bicarbonate. The mixture was extracted with dichloromethane, and the organic layers were combined and concentrated in vacuo to afford 200 mg (40% yield) of the product as a white solid.
 

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