Triacetoxyperiodinane → HCID 57757922, compound

HRID 2198068Notes

Reaction equation

HRID 2198068 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=4[F:33])=[O:21])=[CH:15][CH:14]=3)[C:9]([CH2:11][OH:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[CH:25][C:24]=4[F:33])=[O:21])=[CH:17][CH:18]=3)[C:9]([CH:11]=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57758061HCID 57758061, compound

Product 1

HCID 57757922HCID 57757922, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{4-[4-amino-6-(hydroxymethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]phenyl}-N′-[2-fluoro-5-(trifluoromethyl)phenyl]urea (40.0 mg, 0.09 mmol) was dissolved in THF (5.0 mL) and to it was added Dess-Martin Periodinane reagent (44.0 mg, 0.10 mmol). The reaction was stirred at rt until HPLC indicated completion of reaction. Reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3/Na2S2O3 1:1 (3×). The aqueous layer was back extracted with EtOAc (2×). Organic was dried (Na2SO4) and evaporated to give a crude oil that was purified via HPLC (10-90% ACN/H2O) to give a yellow solid (35.0 mg, 88%). 1H-NMR (CD3OD) δ 9.76 (s, 1H), 8.61 (d, J=8.0 Hz, 1H), 8.11 (s, 1H), 7.87 (s, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H); MS [M+H]+=459; LCMS RT=2.95 min.

Workup

  1. customcompletion of reaction
  2. customReaction
  3. washwashed with saturated aqueous NaHCO3/Na2S2O3 1:1 (3×)
  4. extractionThe aqueous layer was back extracted with EtOAc (2×)
  5. dry with materialOrganic was dried (Na2SO4)
  6. customevaporated
  7. customto give a crude oil that
  8. customwas purified via HPLC (10-90% ACN/H2O)

Sources & evidence

ORD record
ord-f513998f2fd245be817f32eff28836be
Source dataset
uspto-grants-2012_12
Patent number
US08338595B2

Reaction notes

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