Methanol → HCID 59410231, compound

HRID 2382715Notes

Reaction equation

HRID 2382715 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:13]=2[C:14]#[N:15])=[CH:6][C:5]([S:20]([N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)(=[O:22])=[O:21])=[C:4]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[CH:3]=1.C(#N)C.[OH2:40].CO>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:13]=2[C:14]#[N:15])=[CH:6][C:5]([S:20](=[O:22])(=[O:21])[N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:4]([CH:3]=1)[O:31][CH2:32][CH2:33][CH2:34][C:35]([OH:40])=[O:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6342AcetonitrileHCID 68469291HCID 68469291, compound

Product 1

HCID 59410231HCID 59410231, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-benzenesulfonamide (45 mg, 0.083 mmol) in a mixture of DCM (0.3 mL), acetonitrile (0.3 mL) and water (0.4 mL) was added NaIO4 (54 mg, 0.25 mmol) and RuCl3 (2.7 mg, 0.013 mmol). After stirring at rt for 20 minutes, 0.5 mL of methanol was added. The mixture was stirred for 5 minutes, filtered, and purified by prep. LCMS to afford 4-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(methyl-pyridin-2-yl-sulfamoyl)-phenoxy]-butyric acid 18-1. MS: 555.1 (M+H)+; tR=7.61 min (method 2).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. filtrationfiltered
  3. custompurified by prep

Sources & evidence

ORD record
ord-648bba1398964d06a248e6a9cac889e4
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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