Sodium hydride → HCID 69252175, compound

HRID 2370918Notes

Reaction equation

HRID 2370918 reaction equation
[CH:1]1([N:6]2[CH:10]=[C:9]([CH:11]([C:20]([O:22][CH3:23])=[O:21])[C:12]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])[N:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([NH:34]C(=O)OC(C)(C)C)=[N:32][CH:33]=1>CN(C=O)C>[NH2:34][C:31]1[N:32]=[CH:33][C:28]([CH2:27][C:11]([C:9]2[N:8]=[CH:7][N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:10]=2)([C:20]([O:22][CH3:23])=[O:21])[C:12]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:13])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 69250022HCID 69250022, compound

Product 1

HCID 69252175HCID 69252175, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopentyl methyl 2-(1-cyclopentyl-1H-imidazol-4-yl)malonate (0.46 g; 1.44 mmol) was dissolved in absolute DMF (5 ml). At 0° C., sodium hydride (50%; 0.07 g; 1.44 mmol) was added. The mixture was stirred at RT for 1 h and then cooled again to 0° C. Then tert-butyl (5-bromomethylpyridin-2-yl)carbamate (0.41 g; 1.44 mmol) was added, and the mixture was stirred at RT for 2 h. While cooling in ice, the mixture was quenched with H2O and then extracted twice with EA. The organic phase was separated off and dried over Na2SO4, and the solvent was removed under reduced pressure. Purification of the crude product through a cartridge (50 g of silica gel) resulted in 0.31 g of cyclopentyl methyl 2-(6-aminopyridin-3-ylmethyl)-2-(1-cyclopentyl-1H-imidazol-4-yl)malonate.

Workup

  1. temperaturecooled again to 0° C
  2. stirringthe mixture was stirred at RT for 2 h
  3. temperatureWhile cooling in ice
  4. customthe mixture was quenched with H2O
  5. extractionextracted twice with EA
  6. customThe organic phase was separated off
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the crude product through a cartridge (50 g of silica gel)
  10. customresulted in 0.31 g of cyclopentyl methyl 2-(6-aminopyridin-3-ylmethyl)-2-(1-cyclopentyl-1H-imidazol-4-yl)malonate

Sources & evidence

ORD record
ord-bc574569b3154dbb9c474d40f948e8b3
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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