Lithium Hydroxide → 3-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic Acid

HRID 2261856Notes

Reaction equation

HRID 2261856 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:13]2[C:14]([CH3:40])=[N:15][C:16]([O:19][CH2:20][C:21]3[N:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][C:36]([F:39])([F:38])[F:37])[N:23]=[CH:24][C:25]=3[CH:26]([CH3:28])[CH3:27])=[CH:17][CH:18]=2)[CH3:12])[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[CH:26]([C:25]1[CH:24]=[N:23][N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][C:36]([F:38])([F:39])[F:37])[C:21]=1[CH2:20][O:19][C:16]1[N:15]=[C:14]([CH3:40])[C:13]([N:11]([CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:41])=[O:2])[CH3:12])=[CH:18][CH:17]=1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675279973-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic acid methyl ester

Product 1

HCID 247803693-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To an ambient temperature solution of 3-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic acid methyl ester (106 mg, 0.186 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (279 μL, 0.558 mmol, 2.0N in water). The reaction mixture is heated to 50° C. The reaction is concentrated under reduced pressure and the residue is partitioned between Et2O and water. The aqueous layer pH is adjusted to approximately 7 and is extracted with a second portion of Et2O. The combined organic layers are washed with water, dried (MgSO4), filtered, and concentrated to yield the title compound (99 mg, 96%). ES/MS m/e 555.3 (M+1)

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue is partitioned between Et2O and water
  3. extractionis extracted with a second portion of Et2O
  4. washThe combined organic layers are washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-624956b873064090be49e69be6b5d94e
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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