Triacetoxyperiodinane → 2,4-dichloro-N-{4-cyclopropanecarbonyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

HRID 1366860Notes

Reaction equation

HRID 1366860 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[S:31]([NH:34][C:35]1[CH:40]=[C:39]([CH:41]([CH:43]2[CH2:45][CH2:44]2)[OH:42])[C:38]([S:46][C:47]2[CH:52]=[CH:51][C:50]([S:53]([N:56]3[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]3)(=[O:55])=[O:54])=[CH:49][CH:48]=2)=[CH:37][N:36]=1)(=[O:33])=[O:32]>ClCCl.C(OCC)(=O)C>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[S:31]([NH:34][C:35]1[CH:40]=[C:39]([C:41]([CH:43]2[CH2:44][CH2:45]2)=[O:42])[C:38]([S:46][C:47]2[CH:52]=[CH:51][C:50]([S:53]([N:56]3[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]3)(=[O:55])=[O:54])=[CH:49][CH:48]=2)=[CH:37][N:36]=1)(=[O:33])=[O:32]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 577182332,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

Product 1

HCID 577182852,4-dichloro-N-{4-cyclopropanecarbonyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamideYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess Martin periodinane (60 mg, 0.14 mmol) was added to a stirred solution of 2,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide (74 mg, 0.12 mmol) in dichloromethane (5 ml) and the mixture stirred at room temperature overnight under nitrogen. The reaction was diluted with ethyl acetate (30 ml), washed with NaHCO3 solution (20 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to give 2,4-dichloro-N-{4-cyclopropanecarbonyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin -2-yl}-benzenesulfonamide as a yellow solid (38 mg, 51%). 1H NMR (CDCl3): 8.32 (1 H, s, py); 8.08 (1 H, d, Ar); 7.57 (2 H, d, Ar); 7.46 (1 H, s, py); 7.36 (1 H, d, Ar); 7.27 (2 H, d, Ar); 2.89 (4 H, m, 2×CH2 pip); 2.17 (1 H, m, COCH); 1.54 (4 H, m, 2×CH2 pip); 1.33 (2 H, m, CH2 pip); 0.82 (4 H, m, 2×CH2 cprop). HPLC (Luna 2, Gradient 5): rt=6.47 minutes. LCMS rt=7.24 minutes, 627 (M+H)+. By a similar method using the appropriate starting materials the following can be prepared:

Workup

  1. washwashed with NaHCO3 solution (20 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-fd0dbc0278284d95a47b8a653f99b204
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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