Imidazole → HCID 131734587, compound

HRID 595312Notes

Reaction equation

HRID 595312 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[F:14][CH:15]([F:40])[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]2[CH:24]=[C:25]([C:30]3[CH:31]=[N:32][N:33]([CH2:35][CH:36]([OH:39])[CH2:37][OH:38])[CH:34]=3)[CH:26]=[C:27]([CH3:29])[CH:28]=2)[N:17]=1>CN(C=O)C.CCOC(C)=O>[Si:10]([O:38][CH2:37][CH:36]([OH:39])[CH2:35][N:33]1[CH:34]=[C:30]([C:25]2[CH:26]=[C:27]([CH3:29])[CH:28]=[C:23]([NH:22][C:18]3[N:17]=[C:16]([CH:15]([F:14])[F:40])[CH:21]=[CH:20][N:19]=3)[CH:24]=2)[CH:31]=[N:32]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 118208676HCID 118208676, compound

Product 1

HCID 131734587HCID 131734587, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Imidazole (0.28 g, 4.16 mmol) and tert-butylchlorodimethylsilane (0.574 g, 3.81 mmol) were added to a solution of 3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propane-1,2-diol (1.3 g, 3.46 mmol) in DMF (12 mL) at 0° C. The mixture was stirred at 0° C. for 90 minutes. The mixture was allowed to warm to room temperature, diluted with EtOAc, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-100% EtOAc/Hexane) to afford 1-((tert-butyldimethylsilyl)oxy)-3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propan-2-ol. MS ESI calc'd. for C24H34F2N5O2Si [M+H]+ 490. found 490.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (0-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-705a8e9be7b74e7594b7cfc52b2ccf18
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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