5-Nitro-2-Furoic Acid → HCID 16730809, Verbindung

HRID 507337

Reaktionsgleichung

Reaktionsgleichung von HRID 507337
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:44][CH:43]=1>CN(C=O)C.C(Cl)Cl>[CH:42]1[C:54]2[NH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[C:45]([O:55][CH2:56][CH:57]([OH:65])[CH2:58][N:59]2[CH2:64][CH2:63][N:62]([C:9]([C:7]3[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:61][CH2:60]2)=[CH:44][CH:43]=1

Komponenten

8

Edukt 5

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16730483HCID 16730483, Verbindung

Produkt 1

HCID 16730809HCID 16730809, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-Nitrofuroic acid (1.56 g, 9.9 mmol) in DMF (30 mL) was added DIPEA (4.3 mL, 24.8 mmol), EDCI (3.18 g, 16.5 mmol), HOBt (0.44 g, 3.3 mmol) followed by the 1-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol (2.7 g, 8.3 mmol, prepared following the procedure described above in step 11, example 26). The reaction mixture was stirred at room temperature for 12 hours and was diluted with DCM (100 mL), washed with water and brine solution. The organic layer was dried on anhydrous Na2SO4, concentrated and purified by silica gel column chromatography, using hexane/EtOAc (4:6) to afford the title compound as yellow colored solid (2.0 g, 51% yield) with m.p: 178-181° C. 1H NMR (400 MHz, DMSO): δ 2.30-2.60 (m, 4H), 2.67-2.69 (m, 2H), 3.63-3.69 (m, 4H), 4.13-4.21 (m, 3H), 5.08 (s, 1H), 6.69 (d, 1H, J=8.0 Hz), 7.06 (d, 1H, J=8.0 Hz), 7.14 (t, 1H, J=8.0 Hz), 7.24-7.36 (m, 3H), 7.44 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=4.0 Hz), 8.22 (d, 1H, 8.0 Hz), and 11.25 (s, 1H). MS m/z: 464.8 (M+1).

Aufarbeitung

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried on anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b1f89fd6d798400ab29c3f617f4af488
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786142B2

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