Sodium Hydroxide → 3-(3-(Pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoic acid

HRID 446315Notes

Reaction equation

HRID 446315 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([NH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=3[C:25]([F:28])([F:27])[F:26])[C:17]([O:19]CC)=[O:18])=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:3][CH:2]=1.[OH-].[Na+]>CCO>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([NH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=3[C:25]([F:28])([F:26])[F:27])[C:17]([OH:19])=[O:18])=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66970285Ethyl 3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoate

Product 1

HCID 669704063-(3-(Pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoate (2.50 g, 6 mmol) was suspended in EtOH (30 ml) and treated with 5N Sodium hydroxide (4 ml). The mixture was stirred at reflux overnight. The reaction was cooled down and the volatiles removed in vacuo. The residue was washed with diluted acetic acid (10:1 water:acetic acid) and then washed with water, to give 3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoic acid as a yellow solid, after drying in a vacuum oven at 60° C. overnight. MS m/z=361 [M+1]+. Calc'd for C17H11F3N4O2: 360.08.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction was cooled down
  3. customthe volatiles removed in vacuo
  4. washThe residue was washed with diluted acetic acid (10:1 water:acetic acid)
  5. washwashed with water

Sources & evidence

ORD record
ord-6136ae04b633421cb718b07fe11948d9
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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