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Chemical Structure| 198417-15-1 Chemical Structure| 198417-15-1

Structure of 198417-15-1

Chemical Structure| 198417-15-1

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Product Details of [ 198417-15-1 ]

CAS No. :198417-15-1
Formula : C15H17NO4
M.W : 275.30
SMILES Code : O=C(C1C(N(CC2=CC=CC=C2)CCC1=O)=O)OCC
MDL No. :MFCD00030997

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Application In Synthesis of [ 198417-15-1 ]

* 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 [ 198417-15-1 ]

[ 198417-15-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 658-27-5 ]
  • [ 198417-15-1 ]
  • 5-benzyl-2-(3-fluorophenyl)-1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-dione [ No CAS ]
  • 2
  • [ 658-27-5 ]
  • [ 198417-15-1 ]
  • C21H22FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In ethanol; at 25℃; for 18h;Inert atmosphere; Sealed tube; Ethyl 1-benzyl-2,4-dioxopiperidine-3-carboxylate (58.5 mg, 0.21 mmol) in EtOH (2 mL) was added to a biotage microwave vial under nitrogen containing 3-Fluorophenyl hydrazine (44.1 mg, 0.35 mmol) at RT. To this stirred reaction mixture was added AcOH (0.024 mL, 0.42 mmol) and then stirred at RT for 18 hours in a sealed microwave vial. The reaction was heated to 140 C for 10 hours in the microwave reactor and cooled to RT. The reaction mixture was evaporated in the Genevac and then redissolved in 2ml DMSO, filtered and the crude product was purified by flash RP chromatography (35g Puriflash, 15mu, HC column), using decreasingly polar mixtures of water (containing 1% NH4OH ) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 5-benzyl-2-(3-fluorophenyl)-1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-dione (40.0 mg, 50.3%) as a white solid.
  • 3
  • [ 7504-94-1 ]
  • [ 198417-15-1 ]
  • C19H21N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In ethanol; at 40℃; for 18h;Inert atmosphere; Sealed tube; <strong>[7504-94-1]2-hydrazinylpyrimidine</strong> (60.6 mg, 0.55 mmol) was added in one portion to ethyl 1-benzyl-2,4-dioxopiperidine-3-carboxylate (101 mg, 0.37 mmol) and acetic acid (42.0 mul, 0.73 mmol) in EtOH (2965 mul) at RT under nitrogen in a biotage microwave tube. The resulting mixture was sealed and heated at 40 C for 18 hours. UPLC-MS shows main product is uncyclised product, trace of cyclised product observed, addtional decarboxylated impurity present. The reaction was heated to 140 C for a total of 9 hours in the microwave reactor and cooled to RT. The reaction mixture was filtered and the crude product was purified by preparative HPLC (Waters XSelect CSH C18 column, 5mu silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH4OH) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 5-benzyl-2-(pyrimidin-2-yl)-1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-dione (15.8 mg, 13.4 %), as a cream solid.
 

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