Trifluoroacetic acid → HCID 117839396, compound

HRID 1477571Notes

Reaction equation

HRID 1477571 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[N:9][C:8]2=[O:26])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:9][C:8]2=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117840115HCID 117840115, compound

Product 1

HCID 117839396HCID 117839396, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (92 mL) of tert-butyl 4-[5-(4-chlorobenzyl)-4-oxo-4,5-dihydro-1,3,5-triazin-2-yl]piperazine-1-carboxylate (9.20 g, 22.7 mmol) synthesized in Reference Synthesis Example 8, trifluoroacetic acid (40 mL) was added and the resultant solution was stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and pH was adjusted to 7 by adding water and saturated sodium bicarbonate aqueous solution. Extraction with ethyl acetate from the resultant liquid was performed three times, and the organic layer was washed with brine. A deposited solid was collected by filtration, washed with water and ethyl acetate, and dried under reduced pressure to obtain the title compound (3.18 g, yield 46%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure and pH
  4. additionby adding water and saturated sodium bicarbonate aqueous solution
  5. extractionExtraction with ethyl acetate from the resultant liquid
  6. washthe organic layer was washed with brine
  7. filtrationA deposited solid was collected by filtration
  8. washwashed with water and ethyl acetate
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-8ad5db770a234f65a645b2e023c4a8ba
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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