Iodo benzene diacetate → N-(4-((2-aminopyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-c arboxamide

HRID 520713

Reaction equation

HRID 520713 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18](C(N)=O)[CH:17]=3)=[C:13]([F:27])[CH:12]=2)=[O:9])[C:4](=[O:28])[N:3]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CCOC(C)=O.CC#[N:58].O>>[NH2:58][C:18]1[CH:17]=[C:16]([O:15][C:14]2[CH:25]=[CH:26][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:28])[N:3]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[CH:12][C:13]=2[F:27])[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 730532674-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamideHCID 86658869EtOAc CH3CN water

Product 1

HCID 73053650N-(4-((2-aminopyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-c arboxamideYield 81%

Procedure

To a solution of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide (2.5 g, 6.0 mmol) in EtOAc/MeCN/H2O (60 mL/60 mL/30 mL) was added iodobenzene diacetate (2.9 g, 9.0 mmol) at 0° C. The reaction was stirred at rt for 2 hours, then concentrated in vacuo. The resulted residue was dissolved with EtOAc (150 mL), washed with saturated aq. NaHCO3 (80 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was washed with DCM/ether (1/10, 22 mL) to give the title compound as a yellow solid (2.09 g, 81% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulted residue was dissolved with EtOAc (150 mL)
  3. washwashed with saturated aq. NaHCO3 (80 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with DCM/ether (1/10, 22 mL)

Sources & evidence

ORD record
ord-835a6f0ed3704225a84ec051756f8cc5
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Linked notes

Loading…