Sulfanilamide → 4-[4-[4,6-Bis(4-fluorophenyl)-2-methylpyrazolo[3,4-b]pyridin-5-yl]pyridin-2-ylamino]benzenesulfonamide

HRID 42610Notes

Reaction equation

HRID 42610 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:12][C:11]3=[N:21][N:22]([CH3:24])[CH:23]=[C:10]3[C:9]=2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:5]=[CH:4][N:3]=1.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:9]2[C:10]3[C:11](=[N:21][N:22]([CH3:24])[CH:23]=3)[N:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:40])=[O:41])=[CH:35][CH:34]=3)[CH:7]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 5333SulfanilamideHCID 86606799HCID 86606799, compound

Product 1

HCID 670149714-[4-[4,6-Bis(4-fluorophenyl)-2-methylpyrazolo[3,4-b]pyridin-5-yl]pyridin-2-ylamino]benzenesulfonamideYield 17.6%

Conditions

Temperature
190 °C

Procedure

A mixture of 5-(2-chloropyridin-4-yl)-4,6-bis(4-fluorophenyl)-2-methylpyrazolo[3,4-b]pyridine (100 mg, 0.23 mmol, obtained in example 190) and 4-aminobenzenesulfonamide (46 mg, 0.27 mmol) was heated at 190° C. overnight. It was allowed to cool and the crude product obtained was purified by chromatography on silica gel using EtOAc as eluent, to afford 23 mg of the desired compound (yield: 17%).

Workup

  1. temperatureto cool
  2. customthe crude product obtained
  3. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-abc0a3995dda4f148fc57b217cac05c7
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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