Methyl iodide → HCID 69059007, compound

HRID 1817318Notes

Reaction equation

HRID 1817318 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:23][CH3:24])[C:11](=[O:22])[N:12]([CH3:21])[C:13]=3[NH:17][C:18](=[O:20])[CH3:19])[C:8]2=[O:25])=[CH:4][CH:3]=1.[C:28]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:23][CH3:24])[C:11](=[O:22])[N:12]([CH3:21])[C:13]=3[N:17]([CH3:28])[C:18](=[O:20])[CH3:19])[C:8]2=[O:25])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 69056896HCID 69056896, compound

Product 1

HCID 69059007HCID 69059007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-[6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-1-yl]acetamide (0.073 g, 0.196 mmol) in 2 mL DMF was added Cs2CO3 (0.084 g, 0.25 mmol) and methyl iodide (0.044 mL, 0.7 mmole) and the reaction was stirred overnight at room temperature. The solvent was removed and the residue was partitioned between CHCl3 and 10% KHSO4, the organic was dried with Na2SO4, filtered and evaporated to give the crude product.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between CHCl3 and 10% KHSO4
  3. dry with materialthe organic was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bcbff920696a4a3eaa3b384aaa6ccac3
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

Loading…