Tetrahydrofuran → N-(6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl)-4-isopropyl-benzenesulfonamide, hydrochloride

HRID 450741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450741
[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][CH:11]3[CH:7]([CH2:8][N:9]([CH2:15][CH2:16][CH3:17])[CH2:10]3)[C:6]=2[CH:5]=[C:4]([Cl:18])[C:3]=1[NH2:19].C([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30])(C)C.O1C[CH2:36][CH2:35][CH2:34]1>>[ClH:1].[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][CH:11]3[CH:7]([CH2:8][N:9]([CH2:15][CH2:16][CH3:17])[CH2:10]3)[C:6]=2[CH:5]=[C:4]([Cl:18])[C:3]=1[NH:19][S:29]([C:24]1[CH:23]=[CH:28][C:27]([CH:35]([CH3:36])[CH3:34])=[CH:26][CH:25]=1)(=[O:30])=[O:31]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 129164822-(Propan-2-yl)benzene-1-sulfonyl chloride2×HCID 670239596,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine

Produkt 1

HCID 131730711N-(6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl)-4-isopropyl-benzenesulfonamide, hydrochloride

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine (100 mg, 0.33 mmol) and polystyrene-bound DMAP (4-(N,N-dimethylamino)pyridine) (loading 1.06 mmol/g, 32 mg) were treated with tetrahydrofuran (10 ml). Subsequently isopropylphenylsulfonyl chloride (73 mg, 0.33 mmol) was added and stirred for 5 hours at 150° C. in the microwave (CEM). Another portion of isopropylphenylsulfonyl chloride and polystyrene-bound DMAP was added and stirring continued for 7 hours at 160° C. in the microwave. The solvent was evaporated under reduced pressure, the residue treated with water (30 ml) and twice extracted with ethyl acetate (2×30 ml). The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give an oil (470 mg). The crude product was purified via HPLC chromatography. Fractions containing the product were combined and the solvent evaporated. The residue was converted into the hydrochloride salt (4 mg, 2%).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 7 hours at 160° C. in the microwave
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue treated with water (30 ml)
  5. extractiontwice extracted with ethyl acetate (2×30 ml)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae853c48d5a44292b77ea7a73be5c9ca
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486984B2

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