Trifluoroacetic acid → HCID 67654654, compound

HRID 2393448Notes

Reaction equation

HRID 2393448 reaction equation
C(OC([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([N:17]3[CH:21]=[N:20][N:19]=[CH:18]3)[CH:16]=[C:11]2[C:10]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:19]1[N:20]=[CH:21][N:17]([C:15]2[CH:16]=[C:11]3[C:10]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9][NH:8][C:12]3=[CH:13][N:14]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 73503327HCID 73503327, compound

Product 1

HCID 67654654HCID 67654654, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-[1-tert-butyloxycarbonyl-5-(1,2,4-triazol-4-yl)pyrrolo[2,3-c]pyridin-3-yl]prop-2-enoate (0.92 g) and trifluoroacetic acid (5 mL) in dry DCM (20 mL) was stirred at ambient temperature under nitrogen for 16 hours. The solvent was evaporated in vacuo and the residue azeotroped with toluene. The residue was chromatographed on silica eluting with 5 to 20% MeOH in DCM to give a cream solid. This was triturated with MeOH and the solid was collected by filtration to afford the title compound (0.4 g, 62%) as a a cream solid. mp 235° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 1.29 (3H, t, J=7.1Hz), 4.21 (2H, q, J=7.1Hz), 6.68 (1H, d, J=16.2Hz), 7.91 (1H, d, J=16.1Hz), 8.33 (1H, s), 8.36 (1H, s), 8.74 (1H, s), 9.35 (2H, s) and 12.44 (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 5 to 20% MeOH in DCM
  4. customto give a cream solid
  5. customThis was triturated with MeOH
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-5587f26b307749abacb340bb9f00c452
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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