Trimethylsilyl iodide → N-(6-(3-chloro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 870002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870002
[Cl:1][C:2]1[C:3]([O:32]C)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([NH:15][C:16]([C:18]2([C:21]3[CH:31]=[CH:30][C:24]4[O:25][C:26]([F:29])([F:28])[O:27][C:23]=4[CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[N:9]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:32])[NH:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[C:10]([NH:15][C:16]([C:18]2([C:21]3[CH:31]=[CH:30][C:24]4[O:25][C:26]([F:28])([F:29])[O:27][C:23]=4[CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14]

Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 91096555N-(3'-chloro-2'-methoxy-3-methyl-2,4'-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Produkt 1

HCID 117640728N-(6-(3-chloro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To N-(3′-chloro-2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (71 mg, 0.15 mmol) in chloroform (2 mL) was added iodotrimethylsilane (90 mg, 0.45 mmol). The reaction mixture was stirred at room temperature for six hours. The reaction mixture was evaporated to dryness and purified by reverse phase preparative liquid chromatography to yield the product as a trifluoroacetic acid salt. The salt was dissolved in dichloromethane (5 mL) and washed with a saturated sodium bicarbonate solution (2×5 mL). The organics were dried over sodium sulfate and evaporated to yield the product (23 mg, 33%). ESI-MS m/z calc. 459.08. found 460.3 (M+1)+. Retention time 1.11 minutes. 1H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H), 9.11 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.55 (m, 1H), 7.44 (d, J=6.6 Hz, 1H), 7.40-7.38 (m, 1H), 7.35-7.32 (m, 1H), 6.11 (d, J=6.6 Hz, 1H), 2.06 (s, 3H), 1.51-1.50 (m, 2H), 1.17-1.15 (m, 2H).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by reverse phase preparative liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21bd8aaf4f6643d485c38150ec44eeaf
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

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