Trichloroisocyanuric Acid → HCID 71515812, compound

HRID 574218Notes

Reaction equation

HRID 574218 reaction equation
[NH2:1][C:2]1[C:3]([C:14]2[O:18][C:17]([C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:16][N:15]=2)=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Cl:26]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(#N)C>[NH2:1][C:2]1[C:3]([C:14]2[O:18][C:17]([C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:16][N:15]=2)=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:10])([F:9])[F:11])[C:7]=1[Cl:26]

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 71515758HCID 71515758, compound

Product 1

HCID 71515812HCID 71515812, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (R)-2-(5-(3-amino-6-methoxy-5-(trifluoromethyl)pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol (Example 2) (150 mg, 0.403 mmol) in acetonitrile (1 ml) was added trichloroisocyanuric acid (37.5 mg, 0.161 mmol) and the resulting mixture was heated using microwave radiation at 100° C. for 30 minutes followed by 125° C. for 10 minutes. The mixture was partitioned between EtOAc and water. The organic portion was separated and washed with sat.NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded the title compound;

Workup

  1. temperaturethe resulting mixture was heated
  2. customat 100° C.
  3. customfor 30 minutes
  4. customThe mixture was partitioned between EtOAc and water
  5. customThe organic portion was separated
  6. washwashed
  7. dry with materialNaHCO3, brine, dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customPurification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-f8d8375556f64031ba7f70d1f844aa0b
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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