Acetone → HCID 46888642, compound

HRID 28871Notes

Reaction equation

HRID 28871 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]5[NH:28][CH:29]=[CH:30][C:23]=45)=[CH:20][N:19](CC=C)[N:18]=3)=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:34][C:35]([CH3:37])=[O:36].O.C[N+]1([O-])CC[O:43]CC1>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[OH:36][CH:35]([CH2:37][OH:43])[CH2:34][N:19]1[CH:20]=[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)[C:17]([C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])=[CH:12][CH:13]=2)=[N:18]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 58979999HCID 58979999, compound

Product 1

HCID 46888642HCID 46888642, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of N-phenyl-N′-{4-[1-(2-propen-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea (0.18 mmol) in 5:1 acetone:water (1.2 mL) was added N-methylmorpholine N-oxide (0.276 mmol) followed by a 2.5% solution of osmium tetroxide in t-butanol (93.5 mg). The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated aqueous sodium sulfate (11 mL), filtered through a pad of celite (rinsing with ethyl acetate) and concentrated in vacuo. The residue was purified by Gilson reverse phase HPLC to afford the title compound as a white solid (14%). ESMS [M+H]+: 469.2

Workup

  1. customThe reaction was quenched with saturated aqueous sodium sulfate (11 mL)
  2. filtrationfiltered through a pad of celite (rinsing with ethyl acetate)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-ea4f79b8798d40bcafd59f1f4439c2e7
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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