Hydrochloric Acid → (4,7-Dichloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591433Notes

Reaction equation

HRID 591433 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([Cl:27])=[CH:11][C:12]([O:15][CH2:16][C:17]3[N:21]([CH3:22])[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[C:13]([Cl:14])[C:8]=2[S:7][CH:6]=1.C1COCC1.[OH-].[Na+].Cl>CO>[Cl:27][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:6][S:7][C:8]=2[C:13]([Cl:14])=[C:12]([O:15][CH2:16][C:17]2[N:21]([CH3:22])[N:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89768823Methyl(4,7-dichloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 118656083(4,7-Dichloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl(4,7-dichloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (167.4 mg), THF (dry) (2.0 mL) and MeOH (2.0 mL) was added 1N NaOH (1.11 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was neutralized with 1N HCl and concentrated in vacuo. The precipitate was collected by filtration, and crystallized from EtOAc-hexane to give the title compound (131 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe precipitate was collected by filtration
  3. customcrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-52ea49f69832498c890ca04188c64ccb
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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