Water → HCID 57387818, compound

HRID 1874570Notes

Reaction equation

HRID 1874570 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:35]=[CH:36][CH:37]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:20]=[CH:21][C:22]3[N:23]([CH:25]=[C:26]([NH:28]C(=O)C(F)(F)F)[N:27]=3)[CH:24]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[OH-].[Na+].O>C(O)C>[NH2:28][C:26]1[N:27]=[C:22]2[CH:21]=[CH:20][C:19]([O:18][C:14]3[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]4[CH:35]=[CH:36][CH:37]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=4)[CH:17]=[CH:16][CH:15]=3)=[CH:24][N:23]2[CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57386824HCID 57386824, compound

Product 1

HCID 57387818HCID 57387818, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]benzamide (400 mg, 0.788 mmol) in ethanol (4.0 mL) was added 1N aqueous sodium hydroxide solution (8.0 mL), and the mixture was stirred at 45° C. for 12 hr. Water (100 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/methanol=100/0→80/20), and fractions containing the desired product were concentrated under reduced pressure to give the title compound (0.35 g, quantitative) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with saturated brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/methanol=100/0→80/20), and fractions
  7. additioncontaining the desired product
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-421d97b7016e411baeb7d81278a0ec4b
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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