Ethanol → HCID 135804515, compound

HRID 1765577Notes

Reaction equation

HRID 1765577 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 (MethodC): 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-7cb41bfe127f49a1a5a2d3dcd41dfa15
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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