Trifluoroacetic acid → HCID 178507322, compound

HRID 45860

Reaction equation

HRID 45860 reaction equation
C([NH:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:26]3[CH:27]=[C:28]([NH:32][C:33]([NH:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=4)=[O:34])[CH:29]=[CH:30][CH:31]=3)=[N:14][N:15](CC3C=CC(OC)=CC=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1)(C)(C)C.FC(F)(F)C(O)=O.[Na]>O>[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:26]3[CH:27]=[C:28]([NH:32][C:33]([NH:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]([F:44])([F:45])[F:43])=[CH:38][CH:37]=4)=[O:34])[CH:29]=[CH:30][CH:31]=3)=[N:14][NH:15][CH:16]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 671847851-(3-{4-[2-(tert-butylamino)pyridin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]urea

Product 1

HCID 178507322HCID 178507322, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

100 mg (0.16 mmol) of 1-(3-{4-[2-(tert-butylamino)pyridin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]urea were dissolved with 5 ml of trifluoroacetic acid and the solution stirred at 70° C. for 6 hours. The mixture was then poured into icy water, neutralized with aqueous sodium hydrogenocarbonate and extracted with ethylacetate. The organic layer was dried over sodium sulphate and evaporated to dryness. The residue was purified by flash-chromatography on a silica gel column (dichloromethane-methanol, from 1% to 10%), giving 63 mg (90%) of the title compound.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated to dryness
  4. customThe residue was purified by flash-chromatography on a silica gel column (dichloromethane-methanol, from 1% to 10%)

Sources & evidence

ORD record
ord-48fd2eb8e607474183172622be198abb
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

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