Hydrochloric Acid → 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-3-fluoro-benzoic acid

HRID 1095976Notes

Reaction equation

HRID 1095976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH:18]([CH3:33])[C:19]([OH:32])([C:24]1[CH:29]=[CH:28][C:27](=[O:30])[N:26]([CH3:31])[CH:25]=1)[C:20]([F:23])([F:22])[F:21])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#N)=[CH:8][C:7]=1[F:14].O1CCOCC1.[OH2:40].Cl.[OH-:42].[K+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH:18]([CH3:33])[C:19]([OH:32])([C:24]1[CH:29]=[CH:28][C:27](=[O:30])[N:26]([CH3:31])[CH:25]=1)[C:20]([F:22])([F:23])[F:21])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:42])=[O:40])=[CH:8][C:7]=1[F:14]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 252105824-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-3-fluoro-benzonitrile

Product 1

HCID 667824974-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-3-fluoro-benzoic acid

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-3-fluoro-benzonitrile (100 mg) in 2 M aqueous KOH solution (5.2 ml) was added dioxane (1 ml). The mixture was stirred at 90° C. for 30 minutes. Water was added and the mixture was acidified with 2 M aqueous HCl. The solid was collected by filtration, washed with water and dried to give the title compound (99 mg) as a colorless solid. MS (m/e, ISP neg. ion)=498.1 [M−H+].

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-722fc46c9d834da1bd604484c1b779f9
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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