Sodium Sulfite → HCID 59706251, compound

HRID 2196612Notes

Reaction equation

HRID 2196612 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]([CH3:46])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[C:25]([C:37]([NH:39][C:40]3[S:44][N:43]=[C:42]([CH3:45])[N:41]=3)=[O:38])=[N:26][C:27]([S:30][C:31]3[N:35]([CH3:36])[CH:34]=[N:33][N:32]=3)=[CH:28][CH:29]=2)=[CH:19][CH:18]=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:12][N+:13]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[C:25]([C:37]([NH:39][C:40]3[S:44][N:43]=[C:42]([CH3:45])[N:41]=3)=[O:38])=[N:26][C:27]([S:30][C:31]3[N:35]([CH3:36])[CH:34]=[N:33][N:32]=3)=[CH:28][CH:29]=2)=[CH:19][CH:18]=1)([CH3:46])[O-:9]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 25065977HCID 25065977, compound

Product 1

HCID 59706251HCID 59706251, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 9.2 mg of m-chloroperbenzoic acid was added to a chloroform solution of 20 mg of 3-({4-[2-(dimethylamino)ethoxy]phenyl}thio)-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide obtained in Example 1, and stirred at 0° C. for 30 minutes. Aqueous sodium sulfite solution was added to it, extracted with chloroform, and the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid]. The solvent of the obtained fraction was evaporated away under reduced pressure to obtain 17.5 mg of the entitled compound as a yellow solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid]
  5. customThe solvent of the obtained fraction was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-4d28f1d8af7e4eba9909b943d8829ff0
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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