Hydrochloric Acid → HCID 57799417, compound

HRID 2101344Notes

Reaction equation

HRID 2101344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:32])[N:15]([CH2:17][C:18]4[C:19]([C:28]([O:30]C)=[O:29])=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)=[CH:4][CH:3]=1.Cl>[OH-].[Na+].C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:32])[N:15]([CH2:17][C:18]4[C:19]([C:28]([OH:30])=[O:29])=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:33]2[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16004873HCID 16004873, compound

Product 1

HCID 57799417HCID 57799417, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title compound was also prepared as follows: A solution of methyl 3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)picolinate (60 mg, 0.11 mmol) in a mixture of 1 M aqueous NaOH (1 mL) and THF (1 mL) was stirred at room temperature for 4 h. After cooling to 0° C., the reaction mixture was neutralized to pH 6-7 by addition of 1 M aqueous HCl solution, then extracted with EtOAc (30 mL×3). The combined EtOAc extracts were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound.

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined EtOAc extracts were washed with saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e2c0d21cdd44a489e8bd7ea3e35740d
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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