Sodium Cyanide → 6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (PYRIDIN-2-YL-METHYL)AMIDE

HRID 2056611

Reaktionsgleichung

Reaktionsgleichung von HRID 2056611
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=O.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1NC.[C-:37]#[N:38].[Na+]>>[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:37][NH:38][C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:26])[F:27])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=[O:2]

Komponenten

4

Edukt 3

HCID 8929Sodium CyanideHCID 207272-Pyridinamine, N-methyl-HCID 668495266-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester

Produkt 1

HCID 160360956-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (PYRIDIN-2-YL-METHYL)AMIDEAusbeute 48 %

Versuchsvorschrift

A mixture of 6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester (0.099 g, 0.25 mmol), pyridin-2-yl-methylamine (0.7 mL) and sodium cyanide (0.245 g, 0.5 mmol) was stirred at ambient temperature overnight and purified by column chromatography to yield the title compound in 48% yield (0.057 g). m.p. 179-181° C. 1H NMR (300 MHz, CDCl3) δ 8.81, 8.59, 8.12, 7.78-7.50, 7.37, 7.21-7.13, 6.93, 4.83, 4.17-3.66, 3.37. 13C NMR (75 MHz, CDCl3) δ 167.6, 163.3, 160.0, 156.5, 149.0, 145.3, 137.0, 134.2, 132.4, 129.5, 127.2, 122.5, 121.9, 112.3, 46.4, 44.6, 44.4, 41.3. MS (ES+) m/z 471 (M+1).

Aufarbeitung

  1. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-573499f9cab24bd8b626bb4deb4811ae
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335658B2

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