Metaperiodic acid → 3-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid

HRID 1848670Notes

Reaction equation

HRID 1848670 reaction equation
I(O)(=O)(=O)=[O:2].[Cl:6][C:7]1[CH:29]=[CH:28][C:10]([C:11]([N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25])[CH3:14])=[O:12])=[CH:9][C:8]=1[C:30]1[CH:31]=[N:32][C:33]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:35]=1[C:36]#[N:37]>CC#N>[Cl:6][C:7]1[CH:29]=[CH:28][C:10]([C:11]([N:13]([CH3:14])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([CH3:27])([CH3:26])[C:24]([OH:2])=[O:25])=[O:12])=[CH:9][C:8]=1[C:30]1[CH:31]=[N:32][C:33]([C:38]([F:41])([F:39])[F:40])=[CH:34][C:35]=1[C:36]#[N:37]

Participants

4

Reactant 2

HCID 65185Metaperiodic acidHCID 686025284-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-[2-(3-hydroxy-2,2-dimethyl-propoxy)-phenyl]-N-methyl-benzamide

Product 1

HCID 593703443-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To periodic acid (68 mg, 0.30 mmol) in CH3CN (200 μL) at 0° C., Cr(VI)oxide (0.7 mg, 0.0073 mmol) was added and the mixture was stirred for 15 min at 0° C. A solution of 4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-[2-(3-hydroxy-2,2-dimethyl-propoxy)-phenyl]-N-methyl-benzamide (29 mg, 0.056 mmol) dissolved in CH3CN (200 μL) was added and the mixture was warmed to rt. After 2 hr at rt, the mixture was filtered, rinsed with CH3CN, concentrated, dissolved in MeOH and purified by prep HPLC yielding 3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-2,2-dimethyl-propionic acid 52-1. MS: 532.3 (M+H)+, tR=3.65 min (method 3).

Workup

  1. additionwas added
  2. temperaturethe mixture was warmed to rt
  3. waitAfter 2 hr at rt
  4. filtrationthe mixture was filtered
  5. washrinsed with CH3CN
  6. concentrationconcentrated
  7. dissolutiondissolved in MeOH
  8. custompurified by prep HPLC

Sources & evidence

ORD record
ord-8a24097174314492b5b13a37d6f2fafb
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

Loading…