Water → HCID 22106093, compound

HRID 1456397Notes

Reaction equation

HRID 1456397 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[C:10]([NH:26][C:27]([NH:29][C:30]2[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][CH:33]=[CH:32][C:31]=2[CH:39]([CH3:41])[CH3:40])=[O:28])[C:9]1=[O:42].[F-].[K+].O>CN(C=O)C>[CH2:7]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[C:10]([NH:26][C:27]([NH:29][C:30]2[C:31]([CH:39]([CH3:40])[CH3:41])=[CH:32][CH:33]=[CH:34][C:35]=2[CH:36]([CH3:38])[CH3:37])=[O:28])[C:9]1=[O:42])[CH2:6][CH2:5][C:4]#[CH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 22105974HCID 22105974, compound

Product 1

HCID 22106093HCID 22106093, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[1-(5-trimethylsilyl-4-pentynyl)-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (81 mg, 0.133 mmol) in DMF (4 ml) was added potassium fluoride (138 mg, 2.38 mmol), and the mixture was stirred at room temperature for 7 hours. The mixture was poured into water, and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and purified by preparative thin layer chromatography to give the title compound (58 mg, 0.14 mmol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe resultant was concentrated under reduced pressure
  5. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a2921f739e3046ebbc7ee441c6186fc5
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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