Trifluoroacetic acid → HCID 59511254, compound

HRID 604314Notes

Reaction equation

HRID 604314 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:26]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[N:25][CH:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[N:27]1([C:26]2[C:21]([N:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[N:22][CH:23]=[CH:24][N:25]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66601690HCID 66601690, compound

Product 1

HCID 59511254HCID 59511254, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1.00 mL, 13.24 mmol, 10 eq) to a solution of 3′-piperidin-1-yl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.46 g, 1.32 mmol, 1 eq) in DCM (10 mL) then stir the mixture at room temperature for 4 hr. Concentrate the reaction mixture, then dissolve in methanol and load on to a 10 g SCX-2 ion exchange cartridge (pre-washed with methanol). Wash with one column volume of methanol then elute with one column volume of 3.5 M ammonia in methanol. Concentrate to give 3′-piperidin-1-yl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.317 g, 0.97%). MS (m/z): 248.2 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture
  2. dissolutiondissolve in methanol
  3. washload on to a 10 g SCX-2 ion exchange cartridge (pre-washed with methanol)
  4. washWash with one column volume of methanol
  5. washthen elute with one column volume of 3.5 M ammonia in methanol
  6. concentrationConcentrate

Sources & evidence

ORD record
ord-b193afb683984110bd83a574b8e54da6
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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