Trifluoroacetic acid → HCID 58382335, compound

HRID 1628114Notes

Reaction equation

HRID 1628114 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]3[CH:12]=[CH:13][N:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5](COCC[Si](C)(C)C)[C:4]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][CH:24]=1)[CH3:2].C(O)(C(F)(F)F)=O.[NH4+].[OH-]>C(Cl)Cl.O>[CH2:1]([C:3]1[C:11]2[N:10]3[CH:12]=[CH:13][N:14]=[C:9]3[CH:8]=[N:7][C:6]=2[NH:5][C:4]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][CH:24]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 58382132HCID 58382132, compound

Product 1

HCID 58382335HCID 58382335, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-(1-Ethyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone (0.12 g, 0.28 mmol) in DCM (2 mL) was treated with TFA (1.50 mL, 19.5 mmol) then stirred at rt for about 45 min. The solvents were evaporated under reduced pressure then the material was dissolved in 1,4-dioxane (2 mL) and treated with ˜28 wt % aqueous NH4OH (1.2 mL, 31 mmol). The mixture was stirred for about 15 min then diluted with water (10 mL). The volatiles were removed by evaporation under reduced pressure (bath temp 40° C., 85 mm Hg) then the mixture was further diluted with water (20 mL). The solids were collected by filtration then the material was dried to constant weight under vacuum at about 60° C. to give 1-(4-(1-ethyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone (0.062 g, 74%): LC/MS (Table 2, Method a) Rt=1.92 min; MS m/z 305 (M+H)+.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionthe material was dissolved in 1,4-dioxane (2 mL)
  3. stirringThe mixture was stirred for about 15 min
  4. customThe volatiles were removed by evaporation under reduced pressure (bath temp 40° C., 85 mm Hg)
  5. additionthe mixture was further diluted with water (20 mL)
  6. filtrationThe solids were collected by filtration
  7. customthe material was dried to constant weight under vacuum at about 60° C.

Sources & evidence

ORD record
ord-a56e34a25c844322a1e3836fb762b461
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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