Water → HCID 57387818, compound

HRID 1800382Notes

Reaction equation

HRID 1800382 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) produced in Example A3(vii) 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 filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→80/20), and fractions containing the object product was 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. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→80/20), and fractions
  7. additioncontaining the object product
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-124103b1d6a14b89a8d5ebcb4193bd58
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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