Hydrochloric Acid → HCID 118092616, compound

HRID 2207383Notes

Reaction equation

HRID 2207383 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:38])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([NH:26][C:27]4[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=4)[CH:23]=[C:22]([CH3:37])[CH:21]=3)=[CH:16][N:15]=2)=[CH:9][CH:8]=1)C.C1COCC1.Cl>CO>[CH3:37][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:38])=[O:5])=[CH:8][CH:9]=3)=[N:15][CH:16]=2)[CH:25]=[C:24]([NH:26][C:27]2[N:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:30]=[CH:29][N:28]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118092678HCID 118092678, compound

Product 1

HCID 118092616HCID 118092616, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (1 M in water, 1.41 mL, 1.41 mmol) was added to a solution of ethyl-4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]oxy}benzoate (349 mg, 0.706 mmol) in methanol (3.53 mL) and stirred at 60° C. for 16 hours. THF (5 mL) was added to the reaction mixture and heated at 60° C. for 6 hours. The reaction was cooled to room temperature and acidified with aqueous 1N HCl. The aqueous layer was extracted with 3:1 CHCl3:isopropanol (3×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]oxy}benzoic acid (114 mg, 0.244 mmol) as a white solid. MS ESI calc'd for C24H18F3N4O3 [M+H]+ 467. found 467.

Workup

  1. temperatureheated at 60° C. for 6 hours
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe aqueous layer was extracted with 3:1 CHCl3
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-083cc8a840e54fbca3ce1c57daecbdf9
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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