Methanol → 4-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butyric acid

HRID 1891373Notes

Reaction equation

HRID 1891373 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:5]([S:14]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH3:28])([CH3:27])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:4][C:3]=1[C:29]1[C:34]([C:35]#[N:36])=[CH:33][C:32]([C:37]([F:40])([F:39])[F:38])=[N:31][CH:30]=1.C(#N)C.[OH2:44].CO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:29]2[CH:30]=[N:31][C:32]([C:37]([F:39])([F:38])[F:40])=[CH:33][C:34]=2[C:35]#[N:36])=[CH:4][C:5]([S:14]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH3:28])([CH3:27])[CH2:19][CH2:18]2)(=[O:15])=[O:16])=[C:6]([CH:7]=1)[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:44])=[O:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6342AcetonitrileHCID 251551005-[2-chloro-5-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-4-(4-hydroxy-butoxy)-phenyl]-2-trifluoromethyl-isonicotinonitrile

Product 1

HCID 251553644-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-[2-chloro-5-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-4-(4-hydroxy-butoxy)-phenyl]-2-trifluoromethyl-isonicotinonitrile 11-1 (65 mg, 0.11 mmol) in a mixture of DCM (0.5 mL), acetonitrile (0.5 mL) and water (0.6 mL) was added NalO4 (71 mg, 0.33 mmol) and RuCl3 (4.5 mg, 0.022 mmol). After stirring at rt for 30 minutes, 0.5 mL of methanol was added. The mixture was stirred for 30 minutes, filtered, and purified by prep. LCMS to afford 4-[5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butyric acid 12-1. MS: 608.1 (M+H)+; tR=5.87 min (method 5).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. filtrationfiltered
  3. custompurified by prep

Sources & evidence

ORD record
ord-b26195c3743c424fb4a097d470fbf74d
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

Loading…