Water → 5-[Benzyl-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonyl)-amino]-2-fluoro-N-isopropyl-benzamide

HRID 62824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62824
[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=1)[C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[O:31]=[C:32]1[NH:37][C:36]2[CH:38]=[C:39]([S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:41][C:35]=2[O:34][CH2:33]1.O>ClCCl>[CH2:1]([N:8]([S:42]([C:39]1[CH:40]=[CH:41][C:35]2[O:34][CH2:33][C:32](=[O:31])[NH:37][C:36]=2[CH:38]=1)(=[O:44])=[O:43])[C:9]1[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=1)[C:14]([NH:16][CH:17]([CH3:18])[CH3:19])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 52002293-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-sulfonyl chlorideHCID 673103385-Benzylamino-2-fluoro-N-isopropyl-benzamide

Produkt 1

HCID 461825985-[Benzyl-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonyl)-amino]-2-fluoro-N-isopropyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-benzylamino-2-fluoro-N-isopropyl-benzamide (30 mg, 0.1 mmol), diisopropylethylamine (37 μL, 0.2 mmol), and 3-oxo-3,4-dihydro-2H-1,4-benzooxazine-6-sulfonyl chloride (52 mg, 0.2 mmol) was refluxed in dry dichloromethane (3 ml) for 18 hrs. On cooling, water (10 ml) was added with stirring. The organic layer was separated, dried (PTFE frit), then concentrated in vacuo. The crude residue was purified by preparative TLC (10% v/v ethyl acetate/dichloromethane) to afford the title compound as an off white solid (23 mg). HPLC retention time 7.72 min. Mass spectrum (ES+) m/z 499 (M+H).

Aufarbeitung

  1. temperatureOn cooling
  2. customThe organic layer was separated
  3. dry with materialdried (PTFE frit)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative TLC (10% v/v ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d87b9b67f16b494887bdf40fd67a8c02
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447033B2

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