Methanol → HCID 59410231, compound

HRID 1891392Notes

Reaction equation

HRID 1891392 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 NalO4 (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-0ba9f0c8a82245cc8df04653f4c0bd5c
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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