Potassium Carbonate → HCID 22252247, compound

HRID 1611963Notes

Reaction equation

HRID 1611963 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[C:6]([NH2:13])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][O:23][CH2:24][CH2:25]I>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[C:6]([N:13]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 34307792-Iodoethyl etherHCID 22252238HCID 22252238, compound

Product 1

HCID 22252247HCID 22252247, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 800 mg (4.47 mmol) 4-methoxy-benzooxazole-2,7-diamine in 40 ml DMF at room temperature were added 2.47 g (17.9 mmol) potassium carbonate and 2.18 g (6.70 mmol) 1-iodo-2-(2-iodo-ethoxy)-ethane and the mixture heated at 60° C. for 48 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, then dried over sodium sulphate and concentrated in vacuo. Flash chromatography (2/98 methanol/dichloromethane, then 10/90 methanol/dichloromethane) afforded 585 mg (53%) 4-methoxy-7-morpholin-4-yl-benzooxazol-2-ylamine as a light brown solid. ES-MS m/e (%): 250 (M+H+, 100).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afdc7b2623844dd6b0d59e2767512259
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

Loading…