Acetonitrile → [5-Amino-3-(2-chloro-phenyl)-pyridazin-4-yl]-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-methanone

HRID 349284

Reaktionsgleichung

Reaktionsgleichung von HRID 349284
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[O:19][N:20]=[C:21]3[C:26]=2[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])=[N:24][N:23]=[CH:22]3)[N:9]=[N:8]1.C(#N)C>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].O>[NH2:20][C:21]1[C:26]([C:18]([C:10]2[N:9]=[N:8][N:7]([CH2:6][C:5]3[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=[C:3]([C:2]([F:42])([F:41])[F:1])[CH:4]=3)[C:11]=2[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[O:19])=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:24]=[N:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 6342AcetonitrileHCID 866012383-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-phenyl)-isoxazolo[3,4-d]pyridazine

Produkt 1

HCID 58804053[5-Amino-3-(2-chloro-phenyl)-pyridazin-4-yl]-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-methanoneAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 3-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-phenyl)-isoxazolo[3,4-d]pyridazine (100 mg, 0.166 mmol), add 8.0 ml of acetonitrile, and 170 μL of water, followed by molybdenum hexacarbonyl (22 mg, 0.083 mmol). Heat the mixture to 80° C. for 4 h., then cool to RT. Pour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm). Concentrate and purify the residue by chromatography (silica gel, hexanes/EtOAc gradient) to provide 42 mg of a yellow solid. Exact Mass 603.1: MS (aspci): m/z=603.9 (M+1), m/z=601.9 (M−1); 1H NMR (300 MHz, CDCl3) δ 8.65–8.80 (m, 3H), 7.79 (s, 1H), 7.65 (br d, J=7.4 Hz, 1H), 7.31 (s, 2H), 7.15–7.00 (m, 2H), 6.96 (d, J=7.4 Hz, 1H), 6.87 (br t, J=7.4 Hz, 1H), 6.12 (br s, 2H), 5.21 (ABq, J=22.5, 7.5 Hz, 2H).

Aufarbeitung

  1. temperaturecool to RT
  2. additionPour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm)
  3. concentrationConcentrate
  4. custompurify the residue by chromatography (silica gel, hexanes/EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-b949b268fd1d4f06a08f53ee566942ca
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179804B2

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