Water → HCID 86587987, compound

HRID 1828202Notes

Reaction equation

HRID 1828202 reaction equation
C(OC(=O)C[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)=[C:11]([C:20]2[CH:33]=[CH:32][C:23]3[N:24]([CH2:30][CH3:31])[C:25](=[O:29])[N:26]([CH2:27][CH3:28])[C:22]=3[CH:21]=2)[CH:10]=[N:9]1)(C)(C)C.Br[CH2:36][C:37](OC(C)(C)C)=[O:38].O.I([O-])(=O)(=O)=O.[Na+]>C(O)(C)(C)C.C(OC(=O)C)C.C(=O)(O)[O-].[Na+].[Os](=O)(=O)(=O)=O>[CH2:30]([N:24]1[C:23]2[CH:32]=[CH:33][C:20]([C:11]3[C:12]([C:13]4[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=4)=[N:8][N:9]([CH2:36][CH:37]=[O:38])[CH:10]=3)=[CH:21][C:22]=2[N:26]([CH2:27][CH3:28])[C:25]1=[O:29])[CH3:31]

Participants

9

Reactant 4

HCID 962WaterHCID 79177tert-Butyl bromoacetateHCID 23581784HCID 23581784, compoundHCID 23667635Sodium periodate

Product 1

HCID 86587987HCID 86587987, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
23 °C

Procedure

5-(1-Allyl-3-m-tolyl-1H-pyrazol-4-yl)-1,3-diethyl-1,3-dihydro-benzoimidazol-2-one (obtained in the using the same procedure as utilized for the preparation of [4-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-5-m-tolyl-pyrazol-1-yl]-acetic acid tert-butyl ester (0.135 g), substituting allyl iodide for t-butyl bromoacetate) (0.107 g) was diluted with t-butanol (3 mL). To this solution was added water (3 mL), sodium periodate (0.120 g) and catalytic osmium tetroxide (0.1 mL, 2.5% solution in t-butanol). The mixture was stirred at 23° C. for 2 hours then was diluted with ethylacetate and saturated sodium bicarbonate and extracted. The organic layer was dried over sodium sulfate and concentrated. Subsequent chromatography on silica gel gave [4-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-m-tolyl-pyrazol-1-yl]-acetaldehyde (0.06 g).

Workup

  1. extractionextracted
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d912a79269a844d1ae63cb1eea64d7eb
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

Loading…