Trifluoroacetic acid → HCID 22106272, compound

HRID 1456384Notes

Reaction equation

HRID 1456384 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[C:11]([NH:27][C:28]([NH:30][C:31]2[C:36]([CH:37]([CH3:39])[CH3:38])=[CH:35][CH:34]=[CH:33][C:32]=2[CH:40]([CH3:42])[CH3:41])=[O:29])[C:10]1=[O:43])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:6]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[C:11]([NH:27][C:28]([NH:30][C:31]2[C:32]([CH:40]([CH3:41])[CH3:42])=[CH:33][CH:34]=[CH:35][C:36]=2[CH:37]([CH3:39])[CH3:38])=[O:29])[C:10]1=[O:43])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22105936HCID 22105936, compound

Product 1

HCID 22106272HCID 22106272, compoundYield 405.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1-tert-butoxycarbonylmethyl)-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (110 mg, 0.19 mmol) in methylene chloride (20 ml) was added trifluoroacetic acid (1 ml, 13 mmol), and the mixture was stirred at room temperature for 1.5 hour. The mixture was concentrated under reduced pressure, diluted with water, and basified with 4N aqueous NaOH solution, and washed with ethyl acetate. The aqueous layer was acidified with 2N aqueous HCl solution, extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and purified by preparative thin layer chromatography to give the title compound (41 mg, 0.77 mmol).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe residue was concentrated under reduced pressure
  8. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-ff96460505c94a3180ee04403e145cd3
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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