Trifluoroacetic acid → HCID 136230085, compound

HRID 2274467Notes

Reaction equation

HRID 2274467 reaction equation
[NH2:1][C:2]1[N:3]([CH2:34][CH3:35])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[N:13](COCC[Si](C)(C)C)[CH:14]=[CH:15][N:16]=1)=[CH:8][CH:7]=[C:6]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([Cl:33])[CH:27]=1)[N:5]=2.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:3]([CH2:34][CH3:35])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)=[CH:8][CH:7]=[C:6]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([Cl:33])[CH:27]=1)[N:5]=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 136377276HCID 136377276, compound

Product 1

HCID 136230085HCID 136230085, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg (0.59 mmol) of impure 2-amino-7-(3-chloro-4-hydroxy-phenyl)-1-ethyl-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-1H-[1,8]naphthyridin-4-one was dissolved in 20 ml DCM. At 0° C., 3.39 g of TFA were added and the mixture was stirred at room temperature for 24 hours. The solution is neutralized by adding an excess of aqueous NaHCO3 solution. The mixture was then extracted three times with DCM. The combined organic phases were dried over MgSO4 and the solvents were evaporated off under reduced pressure. The so-gained raw material was purified on silica gel (DCM:MeOH:NH4OH=4:10.1) yielding 0.035 g of the unprotected title compound.

Workup

  1. extractionThe mixture was then extracted three times with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were evaporated off under reduced pressure
  4. customThe so-gained raw material was purified on silica gel (DCM:MeOH:NH4OH=4:10.1)

Sources & evidence

ORD record
ord-81f3240c0dcb475f8511bf04fb8c89bf
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

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