Trifluoroacetic acid → HCID 67655264, compound

HRID 2393436Notes

Reaction equation

HRID 2393436 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[CH:14]=2)[N:9](C(OC(C)(C)C)=O)[CH:8]=1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:28])[CH:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67689969HCID 67689969, compound

Product 1

HCID 67655264HCID 67655264, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl-3-[1-tert-butyloxycarbonyl-5-(1,2,4-triazol-1-yl)pyrrolo[2,3-c]pyridin-3-yl]prop-2-enoate (1.73 g, 4.5 mmol) and trifluoroacetic acid (5 mL) in dry DCM (20 mL) was stirred at ambient temperature under nitrogen for 5 hours. The solvent was evaporated in vacuo and the residue azeotroped with toluene. The residue was chromatographed on silica eluting with 20% EtOAc in DCM followed by a gradient of 5 to 10% MeOH in DCM to give a colourless solid. This was triturated with ether to give the title compound (1.05 g, 82%) as a colourless solid. mp 235°-238° C. 1H NMR (360 MHz, d6 -DMSO) δ 1.29 (3H, t, J=7.1Hz), 4.20 (2H, q, J=7.1Hz), 6.44 (1H, d, J=16.0Hz), 7.92 (1H, d, J=16.1Hz), 8.22 (1H, s), 8.27 (1H, s), 8.33 (1H, d, J=2.7Hz), 8.76 (1H, s), 9.31 (1H, s) and 12.46 (1H, br s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue azeotroped with toluene
  3. customThe residue was chromatographed on silica eluting with 20% EtOAc in DCM
  4. customto give a colourless solid
  5. customThis was triturated with ether

Sources & evidence

ORD record
ord-9271545f55f047b3a5c917fc731d6090
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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