1,2-Dichloroethane → 8-[4-(1,3-dioxolan-2-yl)phenyl]-3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678774
[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.[CH3:40][N:41]1[CH:45]=[C:44]([C:46](O)=O)[N:43]=[CH:42]1.C(Cl)CCl>CN(C=O)C.O.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:46]([C:44]5[N:43]=[CH:42][N:41]([CH3:40])[CH:45]=5)[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 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

Produkt 1

HCID 594729458-[4-(1,3-dioxolan-2-yl)phenyl]-3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-4 (5 g, 13 mMol), HOBT (1.9 g, 14.3 mMol), and 1-methyl-1H-imidazole-4-carboxylic acid (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 24 mL of acetic acid and was heated to 80° C. in an oil bath for 5 hours. Upon cooling to room temperature, an equal volume of water was added and the resulting suspension was filtered and washed with copious amounts of water. The collected solid was dried azeotropically with toluene three times to yield 13-1 as a tan solid. Mass (M+1) calculated: 475.1877 observed: 475.1871

Aufarbeitung

  1. temperaturewas heated to 80° C. in an oil bath for 5 hours
  2. temperatureUpon cooling to room temperature
  3. filtrationthe resulting suspension was filtered
  4. washwashed with copious amounts of water
  5. dry with materialThe collected solid was dried azeotropically with toluene three times

Quellen und Nachweise

ORD-Eintrag
ord-436cf5f3f54c421ca59b53e27cb5dba5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008317B2

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