Water → HCID 70663509, compound

HRID 878304Notes

Reaction equation

HRID 878304 reaction equation
[N:1]1([CH2:5][CH2:6][S:7][C:8]2[CH:9]=[C:10]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=2)[C:11]([N:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[O:28][CH3:29])[CH3:14])=[O:12])[CH2:4][CH2:3][CH2:2]1.[OH:37]OS([O-])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O.[OH2:56]>CO>[N:1]1([CH2:5][CH2:6][S:7]([C:8]2[CH:9]=[C:10]([CH:30]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:32]=2)[C:11]([N:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[O:28][CH3:29])[CH3:14])=[O:12])(=[O:37])=[O:56])[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 70663289HCID 70663289, compound

Product 1

HCID 70663509HCID 70663509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 3-(2-(azetidin-1-yl)ethylthio)-N-(4-(4-fluoro-2-methoxyphenyl)-pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide (0.05 g, 96.2 μmol, example 259) in MeOH (2 mL) and water (0.5 mL) was added Oxone® (148 mg, 241 μmol) and the white suspension was stirred at room temperature for 3 hours. The reaction mixture was poured on 10% aqueous Na2S2O3 solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The crude product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.05% triethylamine) (20:80 to 98:2). Colorless solid (0.017 g; 32%). MS (ESI): m/z=552.16 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washThe organic layers were washed once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe crude product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-483c5bcc879448c6855e34aa41458b49
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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