Potassium Carbonate → HCID 15684579, compound

HRID 728136Notes

Reaction equation

HRID 728136 reaction equation
[CH2:1]([NH:3][C:4](=[O:25])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[N:15]=[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][N:17]3[CH:23]=2)=[CH:8][C:7]=1O)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O1CCCC1.O>[CH3:22][C:20]1[CH:19]=[CH:18][N:17]2[CH:23]=[C:14]([CH2:13][CH2:12][C:9]3[CH:10]=[CH:11][C:6]4[N:5]=[C:4]([NH:3][CH2:1][CH3:2])[O:25][C:7]=4[CH:8]=3)[N:15]=[C:16]2[CH:21]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 15684657HCID 15684657, compound

Product 1

HCID 15684579HCID 15684579, compoundYield 8.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[2-{4-(3-ethylureido)-3-hydroxyphenyl}ethyl]-7-methylimidazo[1,2-a]pyridine (17.5 g) and polyphosphate ester (170 g) was stirred at 110° to 120° C. for one hour. The reaction mixture was dissolved in a mixture of ethyl acetate, tetrahydrofuran and water and the resultant solution was adjusted to pH 8.0 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The crude product obtained by concentration was purified by alumina column chromatography eluting with chloroform. The eluted fraction containing the desired product was evaporated to give 6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-ethylaminobenzoxazole (1.41 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by alumina column chromatography
  5. washeluting with chloroform
  6. additionThe eluted fraction containing the desired product
  7. customwas evaporated

Sources & evidence

ORD record
ord-3bb1826c535c44288a06888c45aeb05f
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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