Trifluoroacetic acid → HCID 86730145, compound

HRID 1850117Notes

Reaction equation

HRID 1850117 reaction equation
[N:1]1[N:2]=[CH:3][N:4]2[CH2:9][CH2:8][N:7]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C@@H:17]([NH:19]C(=O)OC(C)(C)C)[CH3:18])=[CH:13][CH:12]=3)[CH2:6][C:5]=12.C(O)(C(F)(F)F)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl>[N:1]1[N:2]=[CH:3][N:4]2[CH2:9][CH2:8][N:7]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C@@H:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=3)[CH2:6][C:5]=12

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 86730144HCID 86730144, compound

Product 1

HCID 86730145HCID 86730145, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(4-((5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylcarbamate (168 mg, 0.47 mmol) in DCM (2 mL) was added TFA (2 mL, 26 mmol) slowly at −78° C. The reaction was stirred at room temperature for 1 h then concentrated and diluted with DCM (10 mL). The solution was stirred with 3 eq. of MP-carbonate resin (3.28 mmol/g, Biotage) for 1 hour at room temperature. The resin was removed by filtration and washed (2×5 mL) with DCM. The filtrate was concentrated and the crude residue was used to next step without further purification.

Workup

  1. concentrationthen concentrated
  2. additiondiluted with DCM (10 mL)
  3. customThe resin was removed by filtration
  4. washwashed (2×5 mL) with DCM
  5. concentrationThe filtrate was concentrated
  6. customthe crude residue was used to next step without further purification

Sources & evidence

ORD record
ord-9bf2202a1a084d0187a7341b5ff1d4a9
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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