Trifluoroacetic acid → HCID 57590076, compound

HRID 605970Notes

Reaction equation

HRID 605970 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:22]4[N:23]([N:28]=[CH:29][N:30]=4)[C:24]([Br:27])=[CH:25][N:26]=3)=[CH:16][CH:15]=2)[C:10](=[O:31])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:27][C:24]1[N:23]2[N:28]=[CH:29][N:30]=[C:22]2[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]3=[O:31])=[CH:15][CH:16]=2)=[N:26][CH:25]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866196644-[4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57590076HCID 57590076, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (0.252 mg, 0.6 mmol) in 2:1 DCM:TFA (4.8 mL) is stirred for 1 hour at room temperature. The mixture is then diluted with DCM and basified with sat. NaHCO3. The aqueous layer is extracted with DCM (3×) and the organic layers are combined, dried over MgSO4, filtered and concentrated to afford the title compound as a solid (180 mg, 78%).

Workup

  1. extractionThe aqueous layer is extracted with DCM (3×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c00842db5804befa25a42eb41ccdce7
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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