Hydrochloric Acid → HCID 86659192, compound

HRID 2367428Notes

Reaction equation

HRID 2367428 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](SC)[N:5]=[C:4]([N:10]2[C@H:15]([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][C@H:12]([C:20]([OH:22])=[O:21])[CH2:11]2)[CH:3]=1.O[O:24][S:25]([O-:27])=O.[K+].Cl.[CH3:30]O>O>[Cl:1][C:2]1[N:7]=[C:6]([S:25]([CH3:30])(=[O:27])=[O:24])[N:5]=[C:4]([N:10]2[C@H:15]([C:16]([F:18])([F:19])[F:17])[CH2:14][CH2:13][C@H:12]([C:20]([OH:22])=[O:21])[CH2:11]2)[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86659191HCID 86659191, compound

Product 1

HCID 86659192HCID 86659192, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A suspension of cis-1-[6-chloro-2-(methylthio)-4-pyrimidinyl]-6-(trifluoromethyl)-3-piperidinecarboxylic acid (180 mg, 0.506 mmol) in CH3OH (8 mL) and water (2.5 mL) was cooled in an ice bath and treated slowly with a premixed solution of oxone (778 mg, 1.27 mmol) in water (3 mL). The reaction was stirred at room temperature overnight. The pH was adjusted pH to acidic with 1N HCl and then 5 mL of water was added. The resulting mixture was filtered over fritted funnel to isolate the title compound (79 mg) as a white solid. LC-MS (ES) m/z=388, 390 [M+H]+.

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationThe resulting mixture was filtered over fritted funnel

Sources & evidence

ORD record
ord-8a81719e4584445295b2f6a1f331eb5a
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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