Sodium periodate → 3-(2-{[4-Chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid

HRID 661627Notes

Reaction equation

HRID 661627 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:23]1[CH:24]=[N:25][C:26]([C:30]#[N:31])=[CH:27][C:28]=1[CH3:29].I([O-])(=O)(=O)=[O:33].[Na+]>C(#N)C.ClCCl.O.CO.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH3:9])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][C:19]([OH:33])=[O:20])=[O:7])=[CH:4][C:3]=1[C:23]1[CH:24]=[N:25][C:26]([C:30]#[N:31])=[CH:27][C:28]=1[CH3:29]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 686027404-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

Product 1

HCID 686027573-(2-{[4-Chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid

Reagents, catalysts & solvents 5

HCID 61850Ruthenium trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide 9-1 (30 mg, 0.07 mmol) in acetonitrile (0.25 mL) and dichloromethane (0.25 mL), a solution of sodium periodate (40 mg, 0.19 mmol) in water (0.4 mL) was added followed by ruthenium (III) chloride (2 mg, 0.0096 mmol). The mixture was stirred 15 min, diluted with MeOH, stirred for 15 min and filtered. The filtrate was purified by prep. LCMS to yield 3-(2-{[4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid 11-1. MS [M+H]: 449.8; tR=6.76 min. (method 2)

Workup

  1. stirringstirred for 15 min
  2. filtrationfiltered
  3. customThe filtrate was purified by prep

Sources & evidence

ORD record
ord-c252cc2d118a4ff99ce1578b23bed8b7
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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