Cesium carbonate → N-{2-[4-(5-Cyclopentyloxypyridin-2-yloxy)phenyl]ethyl}acetamide

HRID 1260499Notes

Reaction equation

HRID 1260499 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:22]1([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:7]=3)=[N:16][CH:17]=2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 121051N-AcetyltyramineHCID 583690662-Chloro-5-cyclopentyloxypyridine

Product 1

HCID 44608463N-{2-[4-(5-Cyclopentyloxypyridin-2-yloxy)phenyl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[2-(4-Hydroxyphenyl)ethyl]acetamide (668.3 mg, 3.73 mmol), 2-chloro-5-cyclopentyloxypyridine (737 mg, 3.73 mmol) and cesium carbonate (1.458 g, 4.475 mmol) were treated at 230° C. in 24 ml of DMF in a microwave reactor for 2 h. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate and water. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 8 mg (1%), M+H+: 341.13.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-ba0b39b6a976458a96046ba31a283f6f
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

Loading…