Dimethylformamide → HCID 11750164, compound

HRID 1666550Notes

Reaction equation

HRID 1666550 reaction equation
[H-].[Na+].[CH:3]1(Br)[CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.[CH:14]1([N:19]2[CH2:24][CH2:23][CH:22]([O:25][C:26]3[N:31]=[CH:30][C:29]([C:32]4[CH:33]=[CH:34][C:35](=[O:38])[NH:36][CH:37]=4)=[CH:28][N:27]=3)[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1>O>[CH:14]1([N:19]2[CH2:24][CH2:23][CH:22]([O:25][C:26]3[N:27]=[CH:28][C:29]([C:32]4[CH:33]=[CH:34][C:35]([O:38][CH:3]5[CH2:7][CH2:6][CH2:5][CH2:4]5)=[N:36][CH:37]=4)=[CH:30][N:31]=3)[CH2:21][CH2:20]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 113712202-(1-cyclopentylpiperidin-4-yloxy)-5-(1H-pyridin-2-on-5-yl)pyrimidine

Product 1

HCID 11750164HCID 11750164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% sodium hydride (21 mg) and cyclopentyl bromide were added to a DMF solution (4 ml) of 2-(1-cyclopentylpiperidin-4-yloxy)-5-(1H-pyridin-2-on-5-yl)pyrimidine (120 mg), and stirred at room temperature for 2 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1) to obtain the entitled compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1)
  6. customto obtain the entitled compound

Sources & evidence

ORD record
ord-efec3f051ea04909a7d98a816431971f
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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