Hydrochloric Acid → HCID 59186305, compound

HRID 336397Notes

Reaction equation

HRID 336397 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>[OH-].[Na+].O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59186495HCID 59186495, compound

Product 1

HCID 59186305HCID 59186305, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-{[5-(3-chlorophenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}benzoate (0.50 g, 1.3 mmol, 1 equiv) in 2M sodium hydroxide aqueous solution and 1,4-dioxane was stirred at about 80-90° C. After 3 h, the reaction mixture was neutralized with 6N aqueous hydrochloride acid solution to pH=4-5. The resulting solid was filtered and rinsed sequentially with water, isopropanol, and hexanes. The resulting crude product was used for the next step without further purification (330 mg, >85% purity by HPLC). LCMS (ESI) m/z: 365.0.

Workup

  1. filtrationThe resulting solid was filtered
  2. washrinsed sequentially with water, isopropanol, and hexanes
  3. customThe resulting crude product was used for the next step without further purification (330 mg, >85% purity by HPLC)

Sources & evidence

ORD record
ord-cc05cff889144976b52f516cbdaa6721
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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