Sodium Sulfite → HCID 86659171, compound

HRID 2367235Notes

Reaction equation

HRID 2367235 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][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:21])[CH2:11]2)[CH:3]=1.[CH:29]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:40][S:41]([O-:43])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([S:41]([CH3:29])(=[O:43])=[O:40])[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]([NH:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:21])[CH2:11]2)[CH:3]=1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86659170HCID 86659170, compound

Product 1

HCID 86659171HCID 86659171, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To cis-1-[6-chloro-2-(methylthio)-4-pyrimidinyl]-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (590 mg, 1.350 mmol) in CH2Cl2 (12 mL) was added mCPBA (757 mg, 3.38 mmol), and the reaction mixture was stirred for 1 hour at room temperature. A saturated solution of Na2SO3 was added, and the resulting mixture was stirred for 30 minutes. The mixture was poured onto saturated aqueous NaHCO3 and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to afford the title compound (640 mg) as a white solid. LC-MS (ES) m/z=469, 471 [M+H]+.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b635590ce4a44a394910365a9afeda0
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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