Ethanol → HCID 135804515, compound

HRID 1835196Notes

Reaction equation

HRID 1835196 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1.[CH2:22](O)[CH3:23]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 135804513HCID 135804513, compound

Product 1

HCID 135804515HCID 135804515, compound

Procedure

A solution of 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid (0.02 g) [Example 30] in ethanol (2 mL) was treated with a catalytic amount of paratoluenesulfonic acid. The mixture was refluxed for 4 hours, the solvent removed by evaporation and the precipitate filtered. The solid was then taken in ethyl acetate, the organic layer washed with water, brine, dried over magnesium sulfate and evaporated to give a yellow solid which was subjected to flash chromatography on silica, eluting with ethyl acetate) to give the title compound. MS: 298 (MH+).HPLC (Method C): RT=2.58 minutes.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customthe solvent removed by evaporation
  3. filtrationthe precipitate filtered
  4. washthe organic layer washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a yellow solid which
  8. washeluting with ethyl acetate)

Sources & evidence

ORD record
ord-c5c5e78d78e04ee9b624a89e1695ff94
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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