Trifluoroacetic acid → 2-Piperazin-1-yl-4-thiophen-3-yl-[1,3,5]triazine

HRID 910668Notes

Reaction equation

HRID 910668 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:11]1([C:14]2[N:19]=[C:18]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[N:17]=[CH:16][N:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673878084-(4-Thiophen-3-yl-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673880172-Piperazin-1-yl-4-thiophen-3-yl-[1,3,5]triazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-(4-thiophen-3-yl-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (60 mg, 0.17 mmol) in CH2Cl2 (2 mL) was added TFA (1 mL) dropwise. The resulting solution was allowed to warm to room temperature and stirred overnight. The resulting mixture was concentrated, then re-dissolved in CH2Cl2 and concentrated. The residue was dissolved in a mixture of CH2Cl2/MeOH (4:1, 5 mL), neutralized with Na2CO3, and stirred at room temperature for 30 min. The resulting solid was filtered, washed with CH2Cl2, and the filtrate was concentrated to yield a yellow gummy solid, which was used without purification.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. dissolutionre-dissolved in CH2Cl2
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of CH2Cl2/MeOH (4:1, 5 mL)
  5. stirringstirred at room temperature for 30 min
  6. filtrationThe resulting solid was filtered
  7. washwashed with CH2Cl2
  8. concentrationthe filtrate was concentrated
  9. customto yield a yellow gummy solid, which
  10. customwas used without purification

Sources & evidence

ORD record
ord-7e88ce7f175f4a058ceba29df95eaace
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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