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 2382696Notes

Reaction equation

HRID 2382696 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 NaIO4 (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-1757313323f446cc8bc41304b9a0f9ae
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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