p-Toluenesulfonic acid → HCID 24738172, compound

HRID 1363074Notes

Reaction equation

HRID 1363074 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1.[C:19]1(C)C=CC(S(O)(=O)=O)=C[CH:20]=1>C(O)C>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 58985366HCID 58985366, compound

Product 1

HCID 24738172HCID 24738172, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 mg of 5-(3-amino-1H-indazol-5-yl)furan-2-carboxylic acid and 78 mg of p-toluenesulfonic acid are heated at 75° C. for 3 days in 5 ml of ethanol. The batch is evaporated, water is added, and the mixture is neutralised. The mixture is extracted three times with EA, the combined org. phases are washed with water, dried and evaporated to dryness. Purification by RP chromatography gives 30 mg of ethyl 5-(3-amino-1H-indazol-5-yl)furan-2-carboxylate, corresponding to a yield of 27%.

Workup

  1. customThe batch is evaporated
  2. additionwater is added
  3. extractionThe mixture is extracted three times with EA
  4. washphases are washed with water
  5. customdried
  6. customevaporated to dryness
  7. customPurification by RP chromatography

Sources & evidence

ORD record
ord-445a05b985ad4ed6946c9a300dac5205
Source dataset
uspto-grants-2011_02
Patent number
US07884126B2

Reaction notes

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