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

HRID 556444노트

반응식

HRID 556444 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-61ca815bcb82466193077519d8ac1e1d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058290B2

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