Iodoacetamide → N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874324Notes

Reaction equation

HRID 1874324 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[N:19][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:21][CH:22]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:34])=[N:3]1.C(N(CC)C(C)C)(C)C.CN(C)C=O.I[CH2:50][C:51]([NH2:53])=[O:52]>O>[NH2:53][C:51](=[O:52])[CH2:50][N:19]1[C:20](=[N:23][S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[CH:21]=[CH:22][C:17]([O:16][C:12]2[CH:11]=[C:10]([NH:9][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:34])[CH:5]=3)=[O:8])[CH:15]=[CH:14][CH:13]=2)=[CH:18]1

Participants

6

Reactant 4

HCID 3727IodoacetamideHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 577491871,3-dimethyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

Product 1

HCID 68987305N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,3-dimethyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide (1.11 g, 2.32 mmol), N,N-diisopropylethylamine (424 μL, 2.44 mmol) and N,N-dimethylformamide (7 mL) was stirred at room temperature for 2 hr, iodoacetamide (451 mg, 2.44 mmol) was added and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (883 mg, 71%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationthe residue was collected by filtration
  8. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-582607d9332540ec9b4bfb8f83053473
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…