Benzenesulfonyl chloride → HCID 18674042, compound

HRID 1635934Notes

Reaction equation

HRID 1635934 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[NH2:16][C:17]1[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[C:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[NH:19][N:18]=1>C(N(CC)CC)C>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:20]2[NH:19][N:18]=[C:17]([NH:16][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:21]=2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 155131015-(4-Fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-amine

Product 1

HCID 18674042HCID 18674042, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under a stream of argon gas, 333 mg of benzenesulfonyl chloride was added dropwise to 4 ml of a tetrahydrofuran solution containing 150 mg of 3-amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole and 191 mg of triethylamine, followed by stirring at room temperature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, the resulting residue was purified by column chromatography using 20 g of silica gel [with an elution solvent comprising chloroform-methanol (100:1)]. Thus, 35 mg (15% yield) of the title compound was obtained as a pale-yellow powder.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d38483ec67f497e8e972897d16e96d6
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

Loading…