p-Toluenesulfonic acid → HCID 24959532, compound

HRID 1947013Notes

Reaction equation

HRID 1947013 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[N:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:31][C:32]1[CH:33]=[C:34]([S:38]([NH2:41])(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1>CC(O)C>[N:11]1([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:31][C:32]3[CH:33]=[C:34]([S:38]([NH2:41])(=[O:39])=[O:40])[CH:35]=[CH:36][CH:37]=3)[N:10]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7377Benzenesulfonamide, 3-amino-HCID 59743357HCID 59743357, compound

Product 1

HCID 24959532HCID 24959532, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-(2-methylsulfonyl-pyrimidin-4-yl)-1H-indazole (100 mg, 0.36 mmol) and p-toluenesulfonic acid (139 mg, 0.73 mmol) in i-PrOH (4 ml) was treated with 3-aminobenzene-sulfonamide (251 mg, 1.46 mmol) in a microwave synthesizer at 150° C. for 20 min. The mixture was partitioned between water and ethyl acetate, the organic layer separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was absorbed on silica gel and purified by flash chromatography (EtOAc/hexane, gradient from 30:70 to 50:50) to afford the title compound. This residue was triturated with aqueous NaOH (1 M), the solid collected by filtration, washed with water and dried under vacuum to afford 3-(4-indazol-1-ylpyrimidin-2-ylamino)-benzenesulfonamide (50 mg, 37% yield). MS=367 [M+H]+.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was absorbed on silica gel
  8. custompurified by flash chromatography (EtOAc/hexane, gradient from 30:70 to 50:50)

Sources & evidence

ORD record
ord-7182ec0382c74a769190359a5b897241
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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