Trifluoroacetic acid → HCID 178436402, compound

HRID 1875102Notes

Reaction equation

HRID 1875102 reaction equation
[Cl:1][C:2]1[N:6](COCC[Si](C)(C)C)[CH:5]=[N:4][C:3]=1[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([O:27][C:28]2[CH:33]=[C:32]([C:34]#[N:35])[CH:31]=[C:30]([Cl:36])[CH:29]=2)[C:20]=1[F:37])=[O:16].C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[N:6]=[CH:5][NH:4][C:3]=1[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([O:27][C:28]2[CH:33]=[C:32]([C:34]#[N:35])[CH:31]=[C:30]([Cl:36])[CH:29]=2)[C:20]=1[F:37])=[O:16]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68485100HCID 68485100, compound

Product 1

HCID 178436402HCID 178436402, compoundYield 63.9%

Procedure

A solution of 5-chloro-N-({3-[(3-chloro-5-cyanophenyl)oxy]-4-ethyl-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-4-carboxamide (0.12 g, 0.213 mmol) and TFA (1.641 ml, 21.29 mmol) were stirred at RT under an atmosphere of nitrogen for 16 h then the solution was concentrated under vacuum. The material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA). The desired product was washed with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (50 mL), water (50 mL), dried over MgSO4, filtered and concentrated to give the title compound (0.059 g, 61%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.73 (s, 1H), 7.50 (s, 1H), 7.31 (t, 1H), 7.15-7.22 (m, 3H), 4.64 (s, 2H), 2.58 (q, 2H), 1.15 (t, 3H). LCMS m/z 434.1 (M+H).

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. customThe material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA)
  3. washThe desired product was washed with saturated NaHCO3 solution
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous NaHCO3 solution (50 mL), water (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b31817ea758c42aa8bea19cb891e7370
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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