Pyridine-2-sulfonyl Chloride → N-[3-(2-acetoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulfonamide

HRID 1368655Notes

Reaction equation

HRID 1368655 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:11]([NH:20][S:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)(=[O:30])=[O:29])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3787675Pyridine-2-sulfonyl ChlorideHCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

Product 1

HCID 22282030N-[3-(2-acetoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 5) (750 mg) in dry pyridine (5 ml) at room temperature was added pyridine-2-sulphonyl chloride (748 mg), the mixture was stirred for 72 hours. The reaction was concentrated under reduced pressure and the residue re-evaporated from toluene. The residue was then partitioned between ethyl acetate (20 ml) and water (20 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue re-evaporated from toluene
  3. customThe residue was then partitioned between ethyl acetate (20 ml) and water (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f2f34c19620477d9d4e992802cf7fba
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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