1,2-Dichloroethane → 3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678773
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[NH:30][C:29]([C:31]5[N:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[CH3:53][N:54]1[CH:58]=[C:57]([C:59](O)=O)[N:56]=[CH:55]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)C>[CH3:53][N:54]1[CH:58]=[C:57]([C:59]2[N:12]3[C:3]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[C:7]([C:13]5[CH:18]=[CH:17][C:16]([CH2:19][N:20]6[CH2:21][CH2:22][CH:23]([C:26]7[NH:30][C:29]([C:31]8[N:36]=[CH:35][CH:34]=[CH:33][N:32]=8)=[N:28][N:27]=7)[CH2:24][CH2:25]6)=[CH:15][CH:14]=5)=[N:8][C:9]=4[CH:10]=[CH:11]3)=[N:1][N:2]=2)[N:56]=[CH:55]1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178514342HCID 178514342, Verbindung

Produkt 1

HCID 1784812663-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 11-3 (0.23 g, 0.4 mMol), HOBT (0.06 g, 0.45 mMol), and 1-methyl-1H-imidazole-4-carboxylic acid (0.06 g, 0.45 mMol) in anhydrous DMF (2 mL) was added DIEA (0.13 mL, 0.8 mMol) followed by EDC (0.09 g, 0.5 mMol). The solution was heated in the microwave reactor for 15 minutes at 80° C. Solution was then treated with 0.2 mL of acetic acid and was heated to 80° C. in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+1) calculated: 632.2742 observed: 632.274

Aufarbeitung

  1. temperaturewas heated to 80° C. in the microwave reactor for 20 minutes
  2. temperatureUpon cooling to room temperature
  3. customthe solution was passed through a syringe
  4. filtrationfilter
  5. custompurified on a C18 reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bf05e73271d44b21928093b65535d432
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008317B2

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