Dimethylformamide → 4-Chloro-2-[[2-chloro-4-(methylsulfonyl)phenyl]amino]-benzenepropanoic acid

HRID 910870Notes

Reaction equation

HRID 910870 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[Cl:15][C:16]1[CH:37]=[C:36]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:35]=[CH:34][C:17]=1OC1C=C(C(F)(F)F)C=CC=1CCC(O)=O.CN(C=[O:46])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:12])=[O:46])=[C:10]([NH:9][C:17]2[CH:34]=[CH:35][C:36]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:37][C:16]=2[Cl:15])[CH:11]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 116259773-[2-[2-Chloro-4-(methylsulfonyl)phenoxy]-4-(trifluoromethyl)phenyl]propanoic acidHCID 136907667-Chloro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 115528094-Chloro-2-[[2-chloro-4-(methylsulfonyl)phenyl]amino]-benzenepropanoic acid

Conditions

Temperature
90 °C

Procedure

A solution of the product from step (ii) (0.174 g) and sodium hydride (60% wt. disp. oil, 0.039 g) in DMF (10 ml) was stirred at 50° C. for 1 hour. The product from example 3 step (vi)-(vii) (0.200 g) was added and the mixture was refluxed at 90° C. for 3 hours. The mixture was partitioned between 2M sodium hydroxide and diethyl ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate and the organic layer dried and concentrated under reduced pressure to give an oil. The residue was purified using RP prep HPLC. Yield 0.061 g

Workup

  1. customThe mixture was partitioned between 2M sodium hydroxide and diethyl ether
  2. extractionextracted with ethyl acetate
  3. customthe organic layer dried
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThe residue was purified

Sources & evidence

ORD record
ord-84c433670f8646a5be55f83af31ce6cf
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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