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

HRID 910870
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HRID 910870 반응식
[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
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참가 물질

5

반응물 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

생성물 1

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

반응 조건

온도
90 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-84c433670f8646a5be55f83af31ce6cf
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022248B2

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