Hydrochloric Acid → 4-[({4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amino)-methyl]-2-methoxy-benzoic Acid

HRID 2261870Notes

Reaction equation

HRID 2261870 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][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]3[CH2:28][CH2:27]3)=[CH:15][C:14]=2[CH3:40])[CH3:12])=[CH:6][C:5]=1[O:41][CH3:42].[OH-].[Na+].C1COCC1.Cl>O.CO>[CH:26]1([C:25]2[CH:24]=[N:23][N:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][C:36]([F:37])([F:38])[F:39])[C:21]=2[CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([N:11]([CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[C:5]([O:41][CH3:42])[CH:6]=3)[CH3:12])=[C:14]([CH3:40])[CH:15]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 675285424-[({4-[4-cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amino)-methyl]-2-methoxy-benzoic acid methyl ester

Product 1

HCID 579312864-[({4-[4-Cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amino)-methyl]-2-methoxy-benzoic AcidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[({4-[4-cyclopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amino)-methyl]-2-methoxy-benzoic acid methyl ester (0.30 g, 0.51 mmol), sodium hydroxide (5 N, 0.5 mL), THF (3 mL) and methanol (3 mL) is heated to reflux for 1 h. The reaction is cooled and acidified with 5 N HCl, then diluted with water and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over MgSO4 to give the tile compound (285 mg, 97%) as an off-white foam. LC-ES/MS m/e 582.0 (M+1).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 h
  3. temperatureThe reaction is cooled
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9fddab07bd8c435993b41f31d75a31a3
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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