Imidazole → HCID 59625297, compound

HRID 2192813Notes

Reaction equation

HRID 2192813 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:40][CH:41]([CH3:43])[CH3:42])[CH:21]2[CH2:26][CH:25]([CH2:27]OS(C)(=O)=O)[CH2:24][N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:44]1[CH:48]=[CH:47][N:46]=[CH:45]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:40][CH:41]([CH3:42])[CH3:43])[CH:21]2[CH2:26][CH:25]([CH2:27][N:44]3[CH:48]=[CH:47][N:46]=[CH:45]3)[CH2:24][N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 59625170HCID 59625170, compound

Product 1

HCID 59625297HCID 59625297, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (100 mg) and imidazole (30 mg) were dissolved in N,N-dimethylacetamide (4 ml), cesium carbonate (130 mg) was added and the mixture was stirred at 60° C. for 1 day. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object compound (43.1 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane (10:90-100:0)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ba9b85d228b4df7a5286691c5a70d35
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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