Trifluoroacetic acid → HCID 22106154, compound

HRID 1456387Notes

Reaction equation

HRID 1456387 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]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[CH:16]=2)=[C:7]([NH:37][C:38]([NH:40][C:41]2[C:46]([CH:47]([CH3:49])[CH3:48])=[CH:45][CH:44]=[CH:43][C:42]=2[CH:50]([CH3:52])[CH3:51])=[O:39])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(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]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:16]=2)=[C:7]([NH:37][C:38]([NH:40][C:41]2[C:42]([CH:50]([CH3:51])[CH3:52])=[CH:43][CH:44]=[CH:45][C:46]=2[CH:47]([CH3:49])[CH3:48])=[O:39])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22106046HCID 22106046, compound

Product 1

HCID 22106154HCID 22106154, compoundYield 571.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-butyl-4-[3-{2-(4-tert-butoxycarbonyl-1-piperazinyl)-ethoxy}phenyl]-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (26 mg, 0.035 mmol) in methylene chloride (5 ml) was added trifluoroacetic acid (1 ml, 13 mmol), and the mixture was stirred at room temperature for two hours. The mixture was concentrated under reduced pressure to remove the solvent, and to the residue was added 5% aqueous ammonia (50 ml), and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and the residue was purified by thin layer chromatography (20% methanol in chloroform) to give the title compound (13 mg, 0.20 mmol).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove the solvent
  3. additionto the residue was added 5% aqueous ammonia (50 ml)
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resultant was concentrated under reduced pressure
  9. customthe residue was purified by thin layer chromatography (20% methanol in chloroform)

Sources & evidence

ORD record
ord-df77a22b030c4af1941314cee75ba9d5
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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