Trifluoroacetic acid → HCID 117702497, compound

HRID 1503266Notes

Reaction equation

HRID 1503266 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][C:11]([NH:19]C(=O)OC(C)(C)C)([CH2:12]3)[CH2:10]1)[CH2:16]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][C:11]([NH2:19])([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117702448HCID 117702448, compound

Product 1

HCID 117702497HCID 117702497, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(pyrazin-2-ylethynyl)-1-adamantylcarbamate (108 mg, 0.31 mol) in DCM (3 mL) was added TFA (0.5 mL). After stirring at room temperature for an hour, the reaction was concentrated under reduced pressure. The resulting residue was diluted with DCM (25 mL), washed with Sat. NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to yield 60 mg (78%) of the title compound, 3-(pyrazin-2-ylethynyl)-1-adamantylamine, as a white solid. ESI-MS m/z: 254 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with DCM (25 mL)
  3. washwashed with Sat. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0236e4d941aa4f5aae8e328ad1886ef9
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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