Methanol → HCID 58504729, compound

HRID 2367433Notes

Reaction equation

HRID 2367433 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]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:11]2)[CH:3]=1.O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>O>[Cl:1][C:2]1[N:7]=[C:6]([S:32]([CH3:36])(=[O:34])=[O:31])[N:5]=[C:4]([N:10]2[CH:15]([C:16]([F:18])([F:19])[F:17])[CH2:14][CH2:13][CH:12]([C:20]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:11]2)[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86659194HCID 86659194, compound

Product 1

HCID 58504729HCID 58504729, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A suspension of cis-1-[6-chloro-2-(methylthio)-4-pyrimidinyl]-N-(phenylmethyl)-6-(trifluoromethyl)-3-piperidinecarboxamide (550 mg, 1.236 mmol) in CH3OH (5 mL) and water (1.5 mL) was cooled in an ice bath and treated slowly with a premixed solution of oxone (2280 mg, 3.71 mmol) in water (0.5 mL). The reaction was stirred at room temperature over the weekend. Water (10 mL) was added and the resulting mixture was filtered. The solid was dried in vacuum oven at 35° C. overnight to afford the crude title compound (834 mg) as an off-white solid. LC-MS (ES) m/z=477 [M+H]+.

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationthe resulting mixture was filtered
  3. customThe solid was dried in vacuum oven at 35° C. overnight

Sources & evidence

ORD record
ord-be4ffab9260f4c04b6a941892e15038c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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