Triacetoxyperiodinane → HCID 58799012, compound

HRID 2117105Notes

Reaction equation

HRID 2117105 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22](=[O:34])[CH2:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:20])[C:16]([CH2:18][OH:19])=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22](=[O:34])[CH2:23][C:24]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:20])[C:16]([CH:18]=[O:19])=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58798988HCID 58798988, compound

Product 1

HCID 58799012HCID 58799012, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N1-(3-fluoro-4-(6-(hydroxymethyl)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide (12 mg, 0.026 mmol, Example 41) in 1 mL of THF was added Dess-Martin periodinane (48 mg, 0.11 mmol, Aldrich) at room temperature. The mixture was allowed to stir for 2 h and HPLC analysis indicated total consumption of the starting material. The mixture was filtered through a plug of SiO2, washed with EtOAc. The organic solvent was then removed under reduced pressure and the residue was purified on preparative HPLC to afford the title compound (10 mg, 83%). MS(ESI+) m/z 466.2 (M+H)+.

Workup

  1. customconsumption of the starting material
  2. filtrationThe mixture was filtered through a plug of SiO2
  3. washwashed with EtOAc
  4. customThe organic solvent was then removed under reduced pressure
  5. customthe residue was purified on preparative HPLC

Sources & evidence

ORD record
ord-bd7338fc65ae4f26b64fd891a958dc32
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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