Hydrochloric Acid → HCID 89768809, compound

HRID 591571Notes

Reaction equation

HRID 591571 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([Cl:26])=[CH:11][C:12]([O:14][CH2:15][C:16]3[N:20]([CH3:21])[N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)=[CH:13][C:8]=2[S:7][C:6]=1[CH3:27].C1COCC1.[OH-].[Na+].Cl>CO>[Cl:26][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[C:6]([CH3:27])[S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[N:20]([CH3:21])[N:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89768806HCID 89768806, compound

Product 1

HCID 89768809HCID 89768809, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl(4-chloro-2-methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (184.5 mg), THF (dry) (2.0 mL) and MeOH (2.0 mL) was added 1N NaOH (1.28 mL). The mixture was stirred at room temperature for 2 h and at 50° C. for 1 h. The mixture was neutralized with 1N HCl. The generated precipitate was collected by filtration to give a colorless solid. The solid was crystallized from EtOAc-hexane to give the title compound (161 mg).

Workup

  1. filtrationThe generated precipitate was collected by filtration
  2. customto give a colorless solid
  3. customThe solid was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-cc7f47fefd1e492387b9e516e2b519f1
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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