Trifluoroacetic acid → HCID 22106140, compound

HRID 1456398Notes

Reaction equation

HRID 1456398 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[CH:16]=2)=[C:7]([NH:32][C:33]([NH:35][C:36]2[C:41]([CH:42]([CH3:44])[CH3:43])=[CH:40][CH:39]=[CH:38][C:37]=2[CH:45]([CH3:47])[CH3:46])=[O:34])[C:6]1=[O:48])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH2:23][NH2:24])[CH:16]=2)=[C:7]([NH:32][C:33]([NH:35][C:36]2[C:37]([CH:45]([CH3:46])[CH3:47])=[CH:38][CH:39]=[CH:40][C:41]=2[CH:42]([CH3:44])[CH3:43])=[O:34])[C:6]1=[O:48])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22106109HCID 22106109, compound

Product 1

HCID 22106140HCID 22106140, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(3-tert-butoxycarbonylamino-1-propynyl)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropyl-phenyl)urea (104 mg, 0.16 mmol) in chloroform (5 ml) was added trifluoroacetic acid (1 ml) at under ice-cooling. The mixture was warmed to room temperature, and then stirred for 1.5 hour. The mixture was concentrated under reduced pressure to remove the solvent, and to the residue was added 5% aqueous sodium chloride solution. The mixture was treated with aqueous ammonia to be converted into a free form, and then extracted with ethyl acetate. The oily layer was washed with 5% aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (4% methanol in chloroform) to give the title compound (64 mg, 0.12 mmol).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove the solvent
  4. additionto the residue was added 5% aqueous sodium chloride solution
  5. additionThe mixture was treated with aqueous ammonia
  6. extractionextracted with ethyl acetate
  7. washThe oily layer was washed with 5% aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe resultant was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (4% methanol in chloroform)

Sources & evidence

ORD record
ord-b156eea5be2a4d50bb9f29f67f097b1d
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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