p-Toluenesulfonic acid → HCID 135804515, compound

HRID 549019Notes

Reaction equation

HRID 549019 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.[C:22]1(C)C=CC(S(O)(=O)=O)=C[CH:23]=1>C(O)C>[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

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 135804513HCID 135804513, compound

Product 1

HCID 135804515HCID 135804515, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 para-toluenesulfonic 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-413fdd48391a48a985c91bda323f522f
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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