Sodium Carbonate → 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide

HRID 888265

반응식

HRID 888265 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[F:13][C:14]([F:35])([F:34])[C:15]1[CH:16]=[C:17]([S:21]([CH2:24][CH2:25][S:26][C:27]2[C:32]([NH2:33])=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>S(Cl)(Cl)=O.O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:33][C:32]2[C:27]([S:26][CH2:25][CH2:24][S:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:34])([F:35])[F:13])[CH:16]=3)(=[O:23])=[O:22])=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:8])=[C:4]([O:11][CH3:12])[CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27745454-Fluoro-2-methoxybenzoic acidHCID 67133713[2-[2-[[3-(Trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine

생성물 1

HCID 469178204-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide수율 58%

시약·촉매·용매 2

HCID 24386Thionyl Chloride용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 510 mg (3.0 mmol) 4-fluoro-2-methoxybenzoic acid in thionyl chloride (3 ml) was stirred for 2 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with dioxane (15 ml). Then a solution of 1.09 g (3.0 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) in dioxane (15 ml) and 1.06 g (10.0 mmol) Na2CO3 were added and the mixture was stirred for 16 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water and extracted with EE. The organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Crystallisation (DCM/hexane) of the residue yielded 895 mg (1.7 mmol, 58%) 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]-benzamide. MS: m/z 514.1 [M+H]+.

후처리

  1. concentrationThen the mixture was concentrated to small volume under vacuum
  2. concentrationThen the mixture was concentrated to small volume under vacuum
  3. extractionextracted with EE
  4. washThe organic phase was washed with a saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customCrystallisation (DCM/hexane) of the residue

출처 및 근거

ORD 기록
ord-09b79a31a3b14fc8815f51bfdb85fac3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247573B2

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