2-Dimethylaminopyridine → HCID 10275329, compound

HRID 1060865Notes

Reaction equation

HRID 1060865 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([CH3:23])[C:5]([O:6][C:7]2[C:12]([CH3:13])=[C:11]([CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[CH:10]=[C:9]([CH3:20])[N:8]=2)=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([N:28]=[C:29]=[O:30])[CH2:26][CH3:27].CN(C1C=CC=CN=1)C>ClCCl>[Cl:1][C:2]1[CH:22]=[C:21]([CH3:23])[C:5]([O:6][C:7]2[C:12]([CH3:13])=[C:11]([CH:14]([O:19][C:29](=[O:30])[NH:28][CH2:25][CH2:26][CH3:27])[C:15]([F:16])([F:17])[F:18])[CH:10]=[C:9]([CH3:20])[N:8]=2)=[C:4]([CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 61033Propyl isocyanateHCID 21912157HCID 21912157, compound

Product 1

HCID 10275329HCID 10275329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[2-(4-chloro-2,6-dimethyl-phenoxy)-3,6-dimethyl-pyridin-4-yl]-2,2,2-trifluoro-ethanol (21 mg, 0.0589 mmol), propyl isocyanate (0.1 ml), dimethylaminopyridine (20 mg) in dichloromethane (2 ml) was heated at reflux for 6 hrs. The mixture was quenched with water and extracted with chloroform. The organic layer was separated, dried and concentrated to give 23 mg of yellow solid. The solid was purified by preparative thin layer chromatography (run in 20% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. customThe mixture was quenched with water
  4. extractionextracted with chloroform
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-97bd44a5e3694bec9e9f213dae9770a1
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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