1,2-Dichloroethane → {8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol

HRID 1678777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678777
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[NH:28][NH2:29])[N:13]=2)=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.[C:40](O)(=O)[CH2:41][OH:42].C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C.C(O)(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:40]([CH2:41][OH:42])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

Produkt 1

HCID 59472958{8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-4 (5 g, 13 mMol), HOBT (1.9 g, 14.3 mMol), and glycolic acid (1.2 g, 15.6 mMol) in anhydrous DMF (100 mL) was added EDC (2.7 g, 14.3 mMol). The solution was stirred overnight at ambient temperature. The solution was then treated with 5 mL of glacial acetic acid and was heated to 80° C. in an oil bath for 2 hours. Upon cooling to room temperature, the reaction was diluted with ethyl acetate and washed with NaHCO3 (aq), water, and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to yield 14-1 as a red solid. LC/MS (M+1) calculated: 425.5; observed: 425.6

Aufarbeitung

  1. temperaturewas heated to 80° C. in an oil bath for 2 hours
  2. temperatureUpon cooling to room temperature
  3. washwashed with NaHCO3 (aq), water, and brine
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0bdbee5f9a564cfc82009b91521ade84
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008317B2

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