Hydrochloric Acid → HCID 25097084, compound

HRID 1944353Notes

Reaction equation

HRID 1944353 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]2[C:10]=1[C:11]([CH3:39])=[C:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]3[CH:35]=[CH:34][N:33]([CH:36]([CH3:38])[CH3:37])[N:32]=3)=[CH:27][CH:26]=1)[C:13]([O:20][CH:21]([F:23])[F:22])=[N:14]2)(C)(C)C.[OH-].[Na+].Cl>O1CCCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:9]([O:8][CH2:7][C:6]([OH:40])=[O:5])=[C:10]2[C:15]=1[N:14]=[C:13]([O:20][CH:21]([F:22])[F:23])[C:12]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]3[CH:35]=[CH:34][N:33]([CH:36]([CH3:38])[CH3:37])[N:32]=3)=[CH:29][CH:30]=1)=[C:11]2[CH3:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67457414HCID 67457414, compound

Product 1

HCID 25097084HCID 25097084, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {8-chloro-2-difluoromethoxy-3-[4-(1-isopropyl-1H-pyrazol-3-yl)benzyl]-4-methylquinolin-5-yloxy}acetic acid tert-butyl ester (0.24 g) in tetrahydrofuran (5.0 mL) was treated with 1.0M aqueous sodium hydroxide solution (0.64 mL), and the resulting mixture was stirred at room temperature for 16 hour. The mixture was neutralised by the addition of 1.0M aqueous hydrochloric acid solution (0.64 mL) and then concentrated under reduced pressure. Purification of the residue by preparative reverse-phase HPLC gave the title compound as a white solid (0.051 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification of the residue by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-0fb7bd8320e0459fb3782abf57355f21
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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