Pyridine → HCID 69804326, compound

HRID 1976394Notes

Reaction equation

HRID 1976394 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[NH:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[N:11]([S:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

Product 1

HCID 69804326HCID 69804326, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.35 g (5.233 mmol) of the product of Example 50 dissolved in 20 mL of chloroform and 1.5 mL of pyridine was added 1.02 g (5.233 mmol) of 4-fluorobenzenesulfonyl chloride and the resulting mixture was stirred overnight at room temperature. The chloroform was removed in vacuo and the residue was diluted with ether and washed with water, 5% HCl solution and saturated sodium bicarbonate solution and then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether/hexanes (1:1) and the solid was collected by filtration and dried in vacuo to provide 1.50 g (69%) of the sulfonamide as a white solid. Electrospray Mass Spec: 416.9 (M+H)+

Workup

  1. customThe chloroform was removed in vacuo
  2. additionthe residue was diluted with ether
  3. washwashed with water, 5% HCl solution and saturated sodium bicarbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ether/hexanes (1:1)
  8. filtrationthe solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d942fd6e00f54fd69be5262b022b770c
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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