Triacetoxyperiodinane → HCID 136348396, compound

HRID 522326Notes

Reaction equation

HRID 522326 reaction equation
[Cl:1][C:2]1[C:3]([C:29]2[NH:30][CH2:31][CH2:32][N:33]=2)=[N:4][N:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:17]=3[CH:18]([CH3:20])[CH3:19])[C:9]2=[O:28])[C:6]=1[CH3:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O>[Cl:1][C:2]1[C:3]([C:29]2[NH:33][CH:32]=[CH:31][N:30]=2)=[N:4][N:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[C:17]=3[CH:18]([CH3:20])[CH3:19])[C:9]2=[O:28])[C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86723039HCID 86723039, compound

Product 1

HCID 136348396HCID 136348396, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-5-methylpyrazol-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.041 g, 0.087 mmol) and Dess-Martin periodinane (0.150 g, 0.35 mmol) in DMSO (2.0 mL) was stirred at 80° C. for 1.5 hr. The mixture was then cooled to room temperature, quenched with sat. aq. NaHCO3 (50 mL), and extracted with EtOAc (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to yield the title compound (0.025 g, TFA salt, 50%). 1H NMR (TFA salt) (400 MHz, CDCl3) δ 7.62 (s, 1H), 7.35 (dd, J=8.4, 4.8 Hz, 2H), 7.16 (m, 4H), 5.15 (dd, J=8.6, 8.6 Hz, 1H), 4.02 (m, 1H), 3.82 (m, 1H), 3.05 (m, 1H), 2.97 (septet, J=7.0 Hz, 1H), 2.35 (s, 3H), 2.70 (m, 1H), 1.18 (d, J=6.8 Hz, 3H), 1.14 (d, J=6.8 Hz, 3H); MS: (ES) m/z calculated for C23H23ClFN7O (free form) [M+H]+ 468.1. found 468.1.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with sat. aq. NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-f477438f9c1049daa749092084348c58
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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