Dimethylamine → HCID 19701623, compound

HRID 862087Notes

Reaction equation

HRID 862087 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([O:20][CH2:21][O:22][CH3:23])=[C:6]([CH:19]=1)[C:7]([C:9]1[C:14]([O:15][CH2:16][O:17][CH3:18])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].[CH3:25][NH:26][CH3:27]>CN(C=O)C>[Cl:1][C:2]1[C:3]([N:26]([CH3:27])[CH3:25])=[CH:4][C:5]([O:20][CH2:21][O:22][CH3:23])=[C:6]([CH:19]=1)[C:7]([C:9]1[C:14]([O:15][CH2:16][O:17][CH3:18])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 10594396HCID 10594396, compound

Product 1

HCID 19701623HCID 19701623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(5-chloro-4-fluoro-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine (1.98 g), a 50% aqueous solution of dimethylamine (20 ml) and DMF (50 ml) was stirred overnight at room temperature. The reaction mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, successively, which was then dried (anhydrous magnesium sulfate). The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography (ethyl acetate/hexane) to afford 2-(5-chloro-4-dimethylamino-2-methoxymethoxybenzoyl)-3-methoxymethoxypyridine (1.82 g) (Compound F-3).

Workup

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous saline solution, successively, which was then dried (anhydrous magnesium sulfate)
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by means of a silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-328ee354e70a4c738c189a3d5c1caa6c
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

Loading…