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

HRID 520722Notes

Reaction equation

HRID 520722 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)=[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: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: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])=[CH:12][CH:13]=2)[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 86658869EtOAc CH3CN waterHCID 1178425924-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamid

Product 1

HCID 73053608N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 48%

Procedure

To a solution of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamid (1.773 g, 3.998 mmol) in EtOAc/MeCN/H2O (20 mL/20 mL/10 mL) was added iodobenzene diacetate (1.6 g, 4.96 mmol) at 0° C. The reaction was stirred at rt overnight, then concentrated in vacuo and diluted with EtOAc (100 mL). The mixture was washed with saturated aq. NaHCO3 (60 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a yellow solid (799 mg, 48%).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc (100 mL)
  3. washThe mixture was washed with saturated aq. NaHCO3 (60 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=30/1)

Sources & evidence

ORD record
ord-6cd25f1834c745f98eb84ae3f774c80b
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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