Sodium Iodide → 1-(2,6-Difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-urea

HRID 1634806Notes

Reaction equation

HRID 1634806 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:3]=1[CH2:4][N:5]([CH:29]([CH3:31])[CH3:30])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][CH:21]([CH:24](OC)[O:25]C)[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1)=[O:7].[I-].[Na+].ClC([SiH3])(Cl)Cl>C(#N)C>[F:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]([CH:29]([CH3:31])[CH3:30])[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([N:18]2[CH2:19][CH2:20][CH:21]([CH:24]=[O:25])[CH2:22][CH2:23]2)(=[O:17])=[O:16])=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 186784841-(2,6-Difluoro-benzyl)-3-[4-(4-dimethoxymethyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-ureaHCID 71317501CID 71317501

Product 1

HCID 186785251-(2,6-Difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under anhydrous conditions, a solution of 1-(2,6-difluoro-benzyl)-3-[4-(4-dimethoxymethyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-urea (0.32 g, 0.6 mmol), sodium iodide (0.228 g, 1.5 mmol), and trichloromethylsilane (0.143 mL, 1.2 mmol) in acetonitrile (2.5 mL) was stirred at ambient temperature for 15 minutes. The reaction mixture was quenched with water and partitioned with methylene chloride. The organic phase was washed with Na2S2O3 dilute solution and dried (Na2SO4). Removal of solvent afforded the crude product which was used directly in the next step without characterization.

Workup

  1. customThe reaction mixture was quenched with water
  2. custompartitioned with methylene chloride
  3. washThe organic phase was washed with Na2S2O3 dilute solution
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-9c102a2e3fef44f5b81767859290d234
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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