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

HRID 888265

反応式

HRID 888265 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24386Thionyl Chloride溶媒HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-09b79a31a3b14fc8815f51bfdb85fac3
出典データセット
uspto-grants-2012_08
特許番号
US08247573B2

関連ノート

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