Triethylamine → (S)-N-[5-(4-Methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-furan-2-carboxamide

HRID 131130

Reaktionsgleichung

Reaktionsgleichung von HRID 131130
[NH2:1][C@H:2]1[CH2:7][C:6]2[C:8]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.C(N(CC)CC)C.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:18][N:15]1[CH2:14][CH2:13][N:12]([C:8]2[C:6]3[CH2:7][C@H:2]([NH:1][C:31]([C:27]4[O:26][CH:30]=[CH:29][CH:28]=4)=[O:32])[CH2:3][O:4][C:5]=3[CH:11]=[CH:10][CH:9]=2)[CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 11139461(S)-3-amino-5-(4-methylpiperazin-1-yl)-1,4-dihydro-2H-1-benzopyran

Produkt 1

HCID 54000140(S)-N-[5-(4-Methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-furan-2-carboxamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled stirred solution of (S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (230 mg, 0.930 mmol) and triethylamine (194 μL, 1.39 mmol) in anhydrous methylene chloride (10 mL) was added 2-furoyl chloride (101 μL, 1.02 mmol) under nitrogen. The ice-bath was removed, and the reaction mixture was allowed to reach room temperature. The mixture was washed with a 2 M NH3 solution, dried (MgSO4), and the solvent was removed in vacuo. The remains was purified on a chromatotron (accelerated thin layer chromatography, eluent: chloroform/ethanol; 92:8+0.5% conc. NH3) affording 249 mg (79% yield) of the title compound as a white solid: mp sinters >50° C.; [α]21D −83° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 341 (52, M+).

Aufarbeitung

  1. customThe ice-bath was removed
  2. customto reach room temperature
  3. washThe mixture was washed with a 2 M NH3 solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe remains was purified on a chromatotron (accelerated thin layer chromatography, eluent: chloroform/ethanol; 92:8+0.5% conc. NH3)

Quellen und Nachweise

ORD-Eintrag
ord-3ce034501a3d408493e9e56ce94ee367
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384943B2

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