Sodium Sulfite → HCID 86608326, compound

HRID 2233980Notes

Reaction equation

HRID 2233980 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[N:23]=[C:22]([O:24][CH2:25][CH2:26]SC)[N:21]=[C:20]([C:29]([NH:31][O:32][CH3:33])=[O:30])[CH:19]=2)[CH2:14][CH2:13]1)=[O:10].[CH:34]1C=C(Cl)C=C(C(OO)=O)C=1.[S:45]([O-:48])([O-])=[O:46].[Na+].[Na+]>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[N:23]=[C:22]([O:24][CH2:25][CH2:26][S:45]([CH3:34])(=[O:48])=[O:46])[N:21]=[C:20]([C:29]([NH:31][O:32][CH3:33])=[O:30])[CH:19]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 86608327HCID 86608327, compound

Product 1

HCID 86608326HCID 86608326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-2-[2-(methylthio)ethoxy]pyrimidine-4-carboxamide (Example 165, 0.10 g, 0.19 mmol) was suspended in DCM (5 ml) and cooled to 0° C. mCPBA (0.067 g, 0.387 mmol, 70%) was added, then the reaction was warmed to room temperature and stirred for 4 h. A further equivalent of mCPBA was added and the mixture was stirred overnight. A solution of sodium sulfite (5%, 3 ml) was added and the layers separated. The aqueous phase was extracted with EtOAc and the combined organic extract was dried over magnesium sulfate and concentrated to give a white solid which was purified by reverse phase chromatography eluting with (20% to 75% acetonitrile in water, 0.1% TFA) affording the title compound (44 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. extractionthe combined organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give a white solid which
  9. customwas purified by reverse phase chromatography
  10. washeluting with (20% to 75% acetonitrile in water, 0.1% TFA)

Sources & evidence

ORD record
ord-d478327e34d54fa7962616469998f427
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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