Water → HCID 21865253, compound

HRID 857675Notes

Reaction equation

HRID 857675 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=4[NH2:28])[CH:13]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30].C([O-])(O)=O.[Na+].O>ClCCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:20][C:19]=4[NH:28][C:29](=[O:31])[CH3:30])[CH:13]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 10474988HCID 10474988, compound

Product 1

HCID 21865253HCID 21865253, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenylamine, (Example 163), (0.25 g, 0.65 mmol) in 1,2-dichloroethane (6.5 mL) was added acetic anhydride (0.15 mL, 1.6 mmol). The mixture was stirred at room temperature for 18 h and then treated with satd NaHCO3 and H2O. The mixture was extracted with EtOAc (2×75 mL) and the combined extracts were washed with H2O (75 mL) and brine (75 mL), dried over Na2SO4, filtered, and concentrated onto silica gel. Purification by silica gel chromatography (gradient, 10 to 40% EtOAc/hexanes) afforded the title compound as a yellow solid. Mp: 137–138° C. MS (ESI, pos. ion) m/z: 479.2 (M+1).

Workup

  1. extractionThe mixture was extracted with EtOAc (2×75 mL)
  2. washthe combined extracts were washed with H2O (75 mL) and brine (75 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel
  6. customPurification by silica gel chromatography (gradient, 10 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-147c5d27b7f94965b4d28b0f9aceddec
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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