Cycloheptanecarbonyl chloride → HCID 58932929, Verbindung

HRID 854088

Reaktionsgleichung

Reaktionsgleichung von HRID 854088
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:20]1([C:27](Cl)=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:27]([CH:20]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[O:28])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 12556870Cycloheptanecarbonyl chlorideHCID 589329182-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamine

Produkt 1

HCID 58932929HCID 58932929, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of amine 8 (0.200 g, 0.78 mmol) in dry Pyridine (5 ml) and cycloheptane carbonyl chloride (0.200 ml, 1.24 mmol) was heated at 80° C. for 2 h. The reaction was quenched by addition of water and the yellow product was filtered, air dried and passed through a SiO2 gel column. Eluting with hexane: EtOAc (6:4) yielded the desired product 18 (0.088 g, 30%); 1H NMR (DMSO-d6, 500 MHz): δ10.38 (1H, brs, NH), 8.76 (1H, brs, NH), 8.44-8.39 (4H, m), 8.33 (1H, brs), 2.92 (1H, m), 1.86-145 (12H, m), EIMS m/z: 380 (M+1), 739.1 (M+).

Aufarbeitung

  1. customThe reaction was quenched by addition of water
  2. filtrationthe yellow product was filtered
  3. customair dried
  4. washEluting with hexane: EtOAc (6:4)

Quellen und Nachweise

ORD-Eintrag
ord-c61ef3c01c324ea6ac68f6e75f2021a0
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256287B2

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