Water → N-[4-(3-Amino-1H-pyrazolo[3,4-b]pyridin-6-yl)phenyl]-2,3-dichlorobenzenesulphonamide

HRID 556444Notes

Reaction equation

HRID 556444 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[NH:14][N:15]=[C:16]([NH2:17])[C:11]3=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34].O>CN(C=O)C>[NH2:17][C:16]1[C:11]2[C:12](=[N:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:33]([C:27]4[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=4[Cl:25])(=[O:35])=[O:34])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[NH:14][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 178507390HCID 178507390, compound

Product 1

HCID 178509221N-[4-(3-Amino-1H-pyrazolo[3,4-b]pyridin-6-yl)phenyl]-2,3-dichlorobenzenesulphonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.44 mmol) of 6-(4-aminophenyl)-1H-pyrazolo[3,4-b]pyridin-3-ylamine are dissolved in 3 ml of anhydrous DMF. The solution is then degassed for 15 minutes with argon. 123.8 μl (89.9 mg, 0.89 mmol, 2 eq.) of triethylamine are subsequently added. The solution is once again degassed for 15 minutes. Finally, 0.109 g (0.444 mmol, 1 eq.) of 2,3-dichlorophenylsulphonyl chloride is added. The solution is stirred at ambient temperature under argon overnight. At the end of the reaction, 10 ml of water are added. A yellow-brown precipitate forms. The mixture is filtered. The solid is dried and purified on a column of 4 g of silica with an eluent gradient of 0 to 10% of methanol in dichloromethane. A beige solid is isolated (11 mg).

Workup

  1. customThe solution is then degassed for 15 minutes with argon
  2. customThe solution is once again degassed for 15 minutes
  3. additionare added
  4. filtrationThe mixture is filtered
  5. customThe solid is dried
  6. custompurified on a column of 4 g of silica with an eluent gradient of 0 to 10% of methanol in dichloromethane
  7. customA beige solid is isolated (11 mg)

Sources & evidence

ORD record
ord-61ca815bcb82466193077519d8ac1e1d
Source dataset
uspto-grants-2011_11
Patent number
US08058290B2

Reaction notes

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