Trifluoroacetic acid → HCID 178494191, compound

HRID 2377971Notes

Reaction equation

HRID 2377971 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:13]([CH3:15])[N:14]=1.FC(F)(F)C(O)=O>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]([C:16]([OH:18])=[O:17])=[C:13]([CH3:15])[N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178494190HCID 178494190, compound

Product 1

HCID 178494191HCID 178494191, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl 2-(4-iodo-2-methoxypyridin-3-yl)-4-methyl-1H-imidazole-5-carboxylate (0.047 g, 0.1131 mmol) in dichloromethane (0.8 mL) was added trifluoroacetic acid (0.6 mL) and the reaction was stirred at room temperature overnight. The solvent was evaporated after adding toluene (1 mL) and the residue was purified on Prep HPLC (trifluoroacetic acid/acetonitrile/water) to give the title material (0.039 g, 96%). 1H NMR (400 MHz, MeOH-d4) δ (ppm): 2.70 (s, 3H) 3.97 (s, 3H) 7.70 (d, J=5.56 Hz, 1H) 8.11 (d, J=5.56 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionafter adding toluene (1 mL)
  3. customthe residue was purified on Prep HPLC (trifluoroacetic acid/acetonitrile/water)

Sources & evidence

ORD record
ord-9288933b89804ab396840c73f5e1cbcb
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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