Trifluoroacetic anhydride → N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874407

Reaction equation

HRID 1874407 reaction equation
[NH2:1][C:2](=O)[CH2:3][N:4]1[C:9](=[N:10]S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=[CH:7][C:6]([O:21][C:22]2[CH:23]=[C:24]([NH:29][C:30]([C:32]3[N:36]([CH3:37])[N:35]=[C:34]([CH3:38])[CH:33]=3)=[O:31])[CH:25]=[C:26]([CH3:28])[CH:27]=2)=[CH:5]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]2[CH:8]=[CH:7][C:6]([O:21][C:22]3[CH:23]=[C:24]([NH:29][C:30]([C:32]4[N:36]([CH3:37])[N:35]=[C:34]([CH3:38])[CH:33]=4)=[O:31])[CH:25]=[C:26]([CH3:28])[CH:27]=3)=[CH:5][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 68987360N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 57749097N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (3.20 g, 5.82 mmol), trifluoroacetic anhydride (20 mL) and dichloromethane (30 mL) was stirred at room temperature for 4 hr. The reaction solution was concentrated under reduced pressure, ethanol (30 mL), water (15 mL) and 8N aqueous sodium hydroxide solution (15 mL) were added to the residue, and the mixture was stirred at room temperature for 60 hr. The reaction solution was concentrated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water and 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 diethyl ether to give the title compound (1.22 g, 56%) as a pale-brown solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, ethanol (30 mL), water (15 mL) and 8N aqueous sodium hydroxide solution (15 mL)
  2. additionwere added to the residue
  3. stirringthe mixture was stirred at room temperature for 60 hr
  4. concentrationThe reaction solution was concentrated under reduced pressure and ethyl acetate
  5. additionwas added to the residue
  6. washThe mixture was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. filtrationthe residue was collected by filtration
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6b0b17adc56d4beebdd3c69b3441f3ce
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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