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Triethylamine → N-[2-Acetyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]-N-(methylsulfonyl)methanesulfonamide

HRID 8784
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8784
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26](=[O:28])[CH3:27].[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[C:26]([C:3]1[O:4][C:5]2=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=[C:10]2[C:2]=1[N:1]([S:30]([CH3:29])(=[O:32])=[O:31])[S:30]([CH3:29])(=[O:32])=[O:31])(=[O:28])[CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 104105121-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

Produkt 1

HCID 10348361N-[2-Acetyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]-N-(methylsulfonyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 0.030 g (0.0696 mmol)of the product from Example 5 in CH2Cl2 (1 mL) cooled to 0° C. was treated with methanesulfonyl chloride (5 μL; 0.0696 mmol), followed by triethylamine (30 μL; 0.209 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 586.9 (M+1), 588.9 (M+3); Rt=4.16 min.

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  3. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-8c635e54935543898c0a9c00395ecef1
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091216B2

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