Ethyl isocyanate → N-{3-[(2-{[(ethylamino)carbonyl]amino}imidazo[1,2-a]pyridin-6-yl) oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874409

Reaction equation

HRID 1874409 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:6][N:5]2[CH:28]=1.[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30]>N1C=CC=CC=1>[CH2:29]([NH:31][C:32]([NH:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:6][N:5]2[CH:28]=1)=[O:33])[CH3:30]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 57749097N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 57749217N-{3-[(2-{[(ethylamino)carbonyl]amino}imidazo[1,2-a]pyridin-6-yl) oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 22%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (301 mg, 0.800 mmol), ethyl isocyanate (100 μL, 1.27 mmol) and pyridine (10 mL) was stirred at 50° C. for 18 hr. The mixture was concentrated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→0/100) and recrystallized from ethyl acetate-hexane to give the title compound (78.0 mg, 22%) as a pale-yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→0/100)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9ca562863e3e4a59960e56df53cc40bd
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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