Water → HCID 21984824, compound

HRID 8822Notes

Reaction equation

HRID 8822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])=[C:16]([NH:17]C(=O)C(F)(F)F)[C:11]2=[CH:10][C:9]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH2:17][C:16]1[C:11]2[C:12](=[N:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[CH:10]=2)[O:14][C:15]=1[C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 219849286-(2-Chlorophenyl)-5-(4-chlorophenyl)-N,N-diethyl-3-[(trifluoroacetyl)amino]-furo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 21984824HCID 21984824, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a magnetically stirred solution of 0.273 g (0.50 mmol) of the product of Example 182 in 5 mL MeOH was added 0.343 g (0.248 mmol) of potassium carbonate and 0.5 mL water. The reaction mixture was stirred at 60° C. for 3 h then cooled to room temperature and partitioned between EtOAc and 10% aq. NaHSO4. The organic extracts were separated, washed with water and brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the titled compound. HPLC/MS: 453.9 (M+1), 455.8 (M+3); Rt=4.15 min.

Workup

  1. temperaturethen cooled to room temperature
  2. custompartitioned between EtOAc and 10% aq. NaHSO4
  3. customThe organic extracts were separated
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 0–20% EtOAc-hexane
  10. customEvaporation of the purified fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-7ac6da8dab584ebf9629637fb9e6f584
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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