Potassium Hydroxide → HCID 56943047, compound

HRID 341412Notes

Reaction equation

HRID 341412 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[O:18][N:17]=2)[N:3]=1.[OH-].[K+].[F:30][C:31]([F:35])([F:34])[CH2:32]I>CS(C)=O.C(OCC)(=O)C>[CH3:15][N:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[C:26]([O:27][CH2:32][C:31]([F:35])([F:34])[F:30])=[CH:25][CH:24]=[CH:23][N:22]=3)[O:18][N:17]=2)[N:5]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 136377133HCID 136377133, compound

Product 1

HCID 56943047HCID 56943047, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{3-[4-amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-pyridin-3-ol (prepared in an analogous manner to Intermediate 58, 85 mg, 0.23 mmol) in DMSO (5 mL) was added potassium hydroxide (77 mg, 138 μmol) and 1,1,1-trifluoro-2-iodo-ethane (159 mg, 760 μmol). The resultant solution was heated at 120 C for 12 h, allowed to cool to room temperature, diluted with ethyl acetate (10 mL) and washed with brine (3×10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by prep HPLC (Method A) to give the title compound as a cream solid (58 mg, 57%).

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by prep HPLC (Method A)

Sources & evidence

ORD record
ord-0eafd2a224454a1da9b817f829d47edc
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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