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

HRID 520703

Reaction equation

HRID 520703 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[N:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20](C(N)=O)[CH:19]=3)=[CH:13][CH:12]=2)=[O:9])[C:4](=[O:27])[N:3]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CCOC(C)=O.CC#[N:57].O>>[NH2:57][C:20]1[CH:19]=[C:18]([O:17][C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:27])[N:3]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[N:16][CH:15]=2)[CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 730532664-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamideHCID 86658869EtOAc CH3CN water

Product 1

HCID 73053627N-(5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 77%

Procedure

To a solution of 4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamide (60 mg, 0.13 mmol) in EtOAc/MeCN/H2O (2 mL/2 mL/1 mL) was added iodobenzene diacetate (54 mg, 0.16 mmol) at 0° C. The reaction was stirred at rt for 2 hours, then concentrated in vacuo. The resulted residue was dissolved in EtOAc (10 mL), washed with saturated aq. NaHCO3, and then dried over anhydrous Na2SO4. The organic solution was concentrated in vacuo to give the title compound as a yellow solid (43 mg, 77%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulted residue was dissolved in EtOAc (10 mL)
  3. washwashed with saturated aq. NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-edb924292f0243a6a1ea7cd403fcefb3
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Linked notes

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