Trifluoroacetic acid → HCID 66744384, compound

HRID 1959446Notes

Reaction equation

HRID 1959446 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19]([CH:33]=[CH2:34])=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:27]1([C:24]2[O:23][C:22]([C:21]3[C:16]([NH2:8])=[N:17][CH:18]=[C:19]([CH:33]=[CH2:34])[N:20]=3)=[N:26][N:25]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744369HCID 66744369, compound

Product 1

HCID 66744384HCID 66744384, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-vinyl-pyrazin-2-yl]carbamate (138 mg, 0.3 mmol) in DCM (0.7 mL) at room temperature under an atmosphere of N2 was added TFA (338 mg, 228 μL, 3 mmol) and reaction mixture was stirred for 20 minutes. The reaction mixture was diluted with DCM and slowly quenched with satd. NaHCO3. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated to yield 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-vinyl-pyrazin-2-amine (67 mg, 85%) as a yellow solid. LC/MS m/z 266.4 [M+H]+.

Workup

  1. customslowly quenched with satd
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-508f4eefd76541e7a6e0add1d73dfb4c
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…