Methyl iodide → HCID 178482204, Verbindung

Reaktionsgleichung

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)=[O:20])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:37]([F:40])([F:39])[F:38])([O-:3])=[O:2].[H-].[Na+].[CH3:43]I>O1CCCC1>[CH3:43][N:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:37]([F:40])([F:39])[F:38])[CH:6]=1)[C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=3)[CH2:25][CH2:26]2)=[O:20])[CH2:13][CH2:12]1

Komponenten

Versuchsvorschrift

2-[Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-ethanone (172 mg, 0.30 mmol, prepared in accordance with Example 11) and sodium hydride (12 mg, 0.30 mmol) were placed under an inert atmosphere. Dry tetrahydrofuran (3 mL) was then added. After gas evolution ceased, methyl iodide (20 μL, 0.31 mmol) was added under stirring to the dark orange colored solution. The resulting mixture was stirred at room temperature. After an hour, HPLC-MS monitoring of the reaction showed about 75% conversion to the desired product. More methyl iodide was added (5 μL, 0.08 mmol), and the mixture was stirred for an additional 30 min. HPLC-MS showed 85% conversion. The mixture was quenched with saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (25 mL). The organic layer was separated, washed with water (10 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum. A yellow oil was isolated. The oil was purified by preparative HPLC. Following lyophilization of the fractions of interest, the desired product was isolated as a yellow solid (106 mg, 59% yield). The structure was confirmed using Protocol I-A. Calculated mass=589; observed mass=589; HPLC retention time=4.69 min.