Methyl iodide → 4-(((5-Chloro-2-thienyl)methyl)(methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

HRID 2203010Notes

Reaction equation

HRID 2203010 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([CH3:27])=[C:22]([CH:24]5[CH2:26][CH2:25]5)[N:23]=4)[CH:20]=3)[C:11](=[O:28])[CH:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:32]>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:32])[C:9]2[CH:14]=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([CH3:27])=[C:22]([CH:24]5[CH2:26][CH2:25]5)[N:23]=4)[CH:20]=3)[C:11](=[O:28])[CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 896901934-(((5-Chloro-2-thienyl)methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

Product 1

HCID 896903694-(((5-Chloro-2-thienyl)methyl)(methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-(((5-chloro-2-thienyl)methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (11.5 mg) in DMF (1 ml) was added NaH (60% in oil, 1.7 mg) at 0° C. After the reaction mixture was stirred at 0° C. for 10 min, iodomethane (2.61 μl) was added to the reaction mixture. The mixture was stirred at room temperature for 3 h. The mixture was quenched with water, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was triturated with IPE, and the resulting solid was collected by filtration and washed with EtOAc-IPE to give the title compound (4.0 mg) as a pale yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with IPE
  9. filtrationthe resulting solid was collected by filtration
  10. washwashed with EtOAc-IPE

Sources & evidence

ORD record
ord-80e5f09fdf0e49cda73d6bc7a8d09cc1
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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