Water → 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoic acid

HRID 1623732Notes

Reaction equation

HRID 1623732 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:24]=3)=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+].O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:24]=3)=[CH:16][C:11]=2[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68108351methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoate

Product 1

HCID 671068932-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoate (may be prepared as described in Description 113; 372 mg, 0.85 mmol) in tetrahydrofuran (25 ml) was added lithium hydroxide (60.8 mg, 2.54 mmol), water (5 ml) and the mixture was refluxed for 4 hours. The mixture was evaporated under reduced pressure on a buchi. The residue was taken up into water (10 ml) and acidified using 2M aqueous HCl to pH 1. The solid formed was filtered, washed with water and dried in air under vacuum to yield the title compound as a light brown solid. 170 mg.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe mixture was evaporated under reduced pressure on a buchi
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried in air under vacuum

Sources & evidence

ORD record
ord-19bc3bce6209481695d7fe26e6c5509b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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