Imidazole → HCID 66839274, compound

HRID 546691Notes

Reaction equation

HRID 546691 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Cl:24][CH2:25][CH:26]([OH:49])[CH2:27][CH:28]([C:40]1[CH:45]=[C:44]([F:46])[C:43]([F:47])=[C:42]([F:48])[CH:41]=1)[C:29]([NH:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[Si:5]([O:49][CH:26]([CH2:25][Cl:24])[CH2:27][CH:28]([C:40]1[CH:45]=[C:44]([F:46])[C:43]([F:47])=[C:42]([F:48])[CH:41]=1)[C:29]([NH:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30])([C:1]([CH3:4])([CH3:3])[CH3:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 66839189HCID 66839189, compound

Product 1

HCID 66839274HCID 66839274, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyldiphenylchlorosilane (0.889 mL), imidazole (233 mg) and DMAP (41.9 mg) were added to a solution of tert-butyl N′-[5-chloro-4-hydroxy-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (680 mg) in DMF (5 mL). The reaction solution was stirred at 60° C. for two hours and then left to cool to room temperature. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 831 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-f5f989d8bd3b43b6bb1dc7d7dbfadc86
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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