m-Chloroperbenzoic acid → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfonyl)isonicotinamide

HRID 2233977Notes

Reaction equation

HRID 2233977 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[C:20]([CH:26]=[C:27]([S:29]([CH3:31])=[O:30])[N:28]=2)[C:21]([NH:23][O:24][CH3:25])=[O:22])[CH2:14][CH2:13]1)=[O:10].C1C=C(Cl)C=C(C(OO)=[O:40])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:19]=[C:20]([CH:26]=[C:27]([S:29]([CH3:31])(=[O:40])=[O:30])[N:28]=2)[C:21]([NH:23][O:24][CH3:25])=[O:22])[CH2:16][CH2:17]1)=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866083232-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfinyl)isonicotinamide

Product 1

HCID 112029112-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfonyl)isonicotinamideYield 11.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-6-(methylsulfinyl)isonicotinamide (Example 152) (90 mg, 0.185 mmol) was dissolved in anhydrous DCM (5 ml). mCPBA (32 mg, 0185 mmol) was added and the mixture was stirred at room temperature for 12 h. The crude mixture was diluted and washed with 10% sodium thiosulfate, water, brine and dried over sodium sulfate and concentrated in vacuo. The brown oil was purified by flash chromatography eluting with acetonitrile/water (0.1% TFA) to give the title compound (11 mg).

Workup

  1. washwashed with 10% sodium thiosulfate, water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe brown oil was purified by flash chromatography
  5. washeluting with acetonitrile/water (0.1% TFA)

Sources & evidence

ORD record
ord-237cfaf1f049413dbc3247154b7c9501
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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