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

HRID 556444ノート

反応式

HRID 556444 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 178507390HCID 178507390、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-61ca815bcb82466193077519d8ac1e1d
出典データセット
uspto-grants-2011_11
特許番号
US08058290B2

反応ノート

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