Trifluoroacetic acid → HCID 68739702, compound

HRID 240781Notes

Reaction equation

HRID 240781 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]#[N:25])[CH:22]=3)[CH:16]=2)[N:11](C(OC(C)(C)C)=O)[N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]#[N:25])[CH:22]=3)[CH:16]=2)[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68736786HCID 68736786, compound

Product 1

HCID 68739702HCID 68739702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(bis(tert-butoxycarbonyl)amino)-5-(1-(cyanomethyl)-1H-pyrazol-4-yl)-1H-indazole-1-carboxylate (0.30 g, 0.557 mmol) in dichloromethane (4.0 mL) was added trifluoroacetic acid (2.0 mL). After about 45 minutes, the reaction was slowly quenched with saturated aqueous sodium bicarbonate. The resulting mixture was extracted with dichloromethane (3×25 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a crude solid. A white precipitate that was suspended in both the initial aqueous layer and the brine layer was filtered and added to the crude solid. The resulting solid was triturated with dichloromethane/methanol (19:1). The remaining solid was collected by vacuum filtration and dried in a vacuum oven at about 70° C. to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.37 (s, 1H), 8.12 (s, 1H), 7.92 (s, 1H), 7.89 (s, 1H) 7.49-7.41 (m, 1H), 7.24 (d, J=8.71 Hz, 1H), 5.52 (s, 2H), 5.31 (s, 2H). MS (ESI+) m/z 239.1 (M+H)+.

Workup

  1. customthe reaction was slowly quenched with saturated aqueous sodium bicarbonate
  2. extractionThe resulting mixture was extracted with dichloromethane (3×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude solid
  8. filtrationthe brine layer was filtered
  9. additionadded to the crude solid
  10. customThe resulting solid was triturated with dichloromethane/methanol (19:1)
  11. filtrationThe remaining solid was collected by vacuum filtration
  12. customdried in a vacuum oven at about 70° C.

Sources & evidence

ORD record
ord-82d360ea46314198bf5bfb346f838055
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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