Diphenyl Ether → 2-Propyl-4H-thiazolo[5,4-b]pyridin-7-one

HRID 607141Notes

Reaction equation

HRID 607141 reaction equation
CC1(C)OC(=O)[C:5](=[CH:9][NH:10][C:11]2[S:15][C:14]([CH2:16][CH2:17][CH3:18])=[N:13][CH:12]=2)[C:4](=O)[O:3]1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:16]([C:14]1[S:15][C:11]2[NH:10][CH:9]=[CH:5][C:4](=[O:3])[C:12]=2[N:13]=1)[CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 668083152,2-Dimethyl-5-[(2-propyl-thiazol-5-ylamino)-methylene]-[1,3]dioxane-4,6-dione

Product 1

HCID 668085072-Propyl-4H-thiazolo[5,4-b]pyridin-7-oneYield 83%

Procedure

The product of Example 5E (230 mg, 0.7781 mmol) was added to refluxing diphenyl ether (5 mL) under a nitrogen atmosphere. After refluxing for 5 minutes, the solution was cooled in an ice bath and diluted with hexanes (50 mL). The resulting golden solid was collected by vacuum filtration and thoroughly washed with hexanes to give the title compound (125 mg, 0.644 mmol, 83%).

Workup

  1. temperatureAfter refluxing for 5 minutes
  2. temperaturethe solution was cooled in an ice bath
  3. filtrationThe resulting golden solid was collected by vacuum filtration
  4. washthoroughly washed with hexanes

Sources & evidence

ORD record
ord-dd6f539f66534e5e83b801c3e67d02ab
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…