Hydrochloric Acid → 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoic acid

HRID 218146

Reaction equation

HRID 218146 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:18]([CH2:23][CH2:24][CH3:25])[C:19]([O:21]C)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl>[OH-].[Na+].CO.CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:18]([CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68706692methyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoate

Product 1

HCID 592511522-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 86640187NaOH MeOH DMSOSolvent

Procedure

Methyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoate was heated to 100° C. overnight in a mixture of 2 M NaOH/MeOH/DMSO (1:1:1). The next day, the reaction was cooled, acidified to pH 5 with HCl and extracted 2× EtOAc. The organic layers were washed with water×2, dried over MgSO4, filtered, concentrated in vacuo, and purified by HPLC to give 140 mg (91% yield) of acid 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl) pentanoic acid. MS found: (M+H)+=403.

Workup

  1. temperatureThe next day, the reaction was cooled
  2. extractionextracted 2× EtOAc
  3. washThe organic layers were washed with water×2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-e1d51a5d7c844edca62c023e791a012f
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Linked notes

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