Hydrochloric Acid → HCID 19823304, compound

HRID 728137Notes

Reaction equation

HRID 728137 reaction equation
[CH2:1]([NH:3][C:4](=[O:25])[NH:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:23]=1O)[CH2:9][C:10]1[N:14]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]2=[N:12][C:11]=1[CH3:20])[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH3:20][C:11]1[N:12]=[C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]2[C:10]=1[CH2:9][C:8]1[CH:21]=[CH:22][C:23]2[O:25][C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15171499HCID 15171499, compound

Product 1

HCID 19823304HCID 19823304, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[3-(3-ethylureido)-4-hydroxybenzyl]-2,7-dimethylimidazo[1,2-a]pyridine (3.7 g) and polyphosphate ester (37 g) was stirred at 110° to 120° C. for one hour. The reaction mixture was dissolved in a mixture of ethyl acetate and water and the resultant solution was acidified to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with aqueous 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on alumina. The fraction eluted with a mixture of chloroform and methanol (98:2 V/V) was collected and the solvent was evaporated in vacuo and the residue was recrystallized from a mixture of chloroform and diethyl ether to give 5-(2,7-dimethylimidazo[1,2-a]pyridin-3-ylmethyl)-2-ethylaminobenzoxazole (0.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. washThe fraction eluted with a mixture of chloroform and methanol (98:2 V/V)
  6. customwas collected
  7. customthe solvent was evaporated in vacuo
  8. customthe residue was recrystallized from a mixture of chloroform and diethyl ether

Sources & evidence

ORD record
ord-5295996bf2ef473ca695133d457976e5
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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